Dear Wendy
Dear Wendy

Your Turn: “Should I Dump my Boyfriend for My Supervisor?”

In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me:

I’m 24 years old and I have a boyfriend of four years. We’ve had our ups and downs through the years as many couples do — I’ve caught him cheating but was dumb enough to keep believing he’d change. I’m currently unhappy with my relationship because I’m the sole bread-winner and my boyfriend lacks ambition. He doesn’t work, is verbally disrespectful towards me, and jealous because I lack trust for him.

I have recently developed feelings for my supervisor at work, who flirts with me all the time. He has everything I deserve: he’s honest, thoughtful, free-spirited, confident and has an unbelievable amount of ambition. I am so attracted to the way he commands the attention when he steps into a room. At work I am the girl he will come to for anything he needs (work-related), and he seems to express interest in me. Recently, I met with him outside of work to hang out. He asked for a back massage and I thought “YES, MY BIG CHANCE!” But nothing happened, even though throughout the massage he got “happy” (couldn’t think of a cleaner way to say that). He suggested we do something and I rejected him. That was hard for me to do because I like him so much, but I’m not that type of girl. He kept assuming I was upset … which I was — at myself, for I felt I lost my chance.

Considering what I have been through with my boyfriend, I want the next man to work for me (my supervisor thinks I’m single by the way). He’s not looking for a relationship because he’s concentrating on buying a condo and setting himself up first, which I respect. He continues to flirt with me, though. How do I know if he’s waiting to be set up to make me his girlfriend or if this is strictly platonic? — Miss Understood

109 comments… add one
  • Kate August 22, 2011, 9:21 am

    YES, break up with your boyfriend. It sounds like a dead relationship that’s going nowhere and definitely not working for you. Sounds like you caught him cheating more than once, since you say you were “dumb enough to think he would change.” That plus verbal abuse, total lack of ambition, and inappropriate jealousy? Yes, move on, no question.

    BUT, do NOT do it because you think you have this other guy on the back burner which makes it a safe exit. You are not leaving your boyfriend “for” this other guy. You’re leaving him because it’s the right thing to do. Do not be afraid of being alone. Being single and available to find the right relationship feels great, and it will be awesome to put all that crap behind you. But do not pursue things with the supervisor. Frankly, he sounds like a creep. Be single, be happy, concentrate on yourself, and use the time to work through what you need to work through.

    Your supervisor should not be flirting, requesting back massages, and trying to hook up with you. That’s gross. He sounds like a guy who’d take advantage and use you for a fling, and why would you potentially put your job on the line to get entangled in something like that? Seriously, do not do it.

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    • fallonthecity August 22, 2011, 9:44 am

      Yeah, I agree that the supervisor sounds pretty creepy.

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    • sohara August 22, 2011, 11:54 am

      I, too, agree that the supervisor sounds like a creep. It is totally inappropriate to ask an employee for a back-rub, even more so for sex. He also sounds stupid, because that could get him fired.

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      • justpeachy August 22, 2011, 3:28 pm

        And how does being in a relationship interfere with buying furniture?

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      Jess of CityGirlsWorld.com August 22, 2011, 11:06 am

      Yes! Please, please, listen to Kate.

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    • retlaw August 23, 2011, 3:06 am

      Wow, modern romance. You’re living with a guy who doesn’t contribute income and cheats on you? You’re 24? Send him home to live in Mom’s basement.

      What’s all this about missing your “big chance” with your supervisor? Are you in love with him, or with his new condo? Are you afraid to be alone, or do you just want to “retire” from the workforce by marrying a moneyed guy?

      Your lack of values has brought you to this pass. You’ll be dissatisfied with what you have and on the make for someone better until you address your values.

      What is it that men are for?

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  • Lindsay August 22, 2011, 9:22 am

    I’m a firm believer that a person should not end a relationship for someone else. If you’re unhappy in your relationship, then by all means, dump your boyfriend. It doesn’t have to be tied to whether you start a new one or not. As for the boss, I find him somewhat creepy. Even if you are attracted to him, the fact that he thinks it’s appropriate to act that way at work, with an employee, doesn’t speak much for his professionalism or chaoracter. Not to mention that buying a condo has no bearing on whether a person can date or not, so to suspect that he doesn’t want a relationship because he doesn’t want a relationship. I say: MOA from the boyfriend and steer clear of your boss.

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    • sleepy August 22, 2011, 9:58 am

      Yeah, the boss is so clearly out of line. Not only is that inappropriate, it can border on sexual harrassment. Don’t let him try to manipulate you.

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      • SpaceySteph August 22, 2011, 10:07 am

        Border? I think this is way beyond the border to sexual harassment. Under no circumstances should your boss ask you for a back massage. Especially if he has a habit of getting aroused under such conditions. NONE.

      • Slamy August 22, 2011, 1:20 pm

        Yep. Your boss isn’t supposed to get a boner by you. Inappropriate.

      • Allison August 23, 2011, 1:19 pm

        Who are the people who are giving these sexual harassment comments a thumbs down?!

      • SpaceySteph August 23, 2011, 1:33 pm

        People who are sleeping with their bosses?

      • Ark August 28, 2011, 2:13 pm

        Count me as one of the people who would give the sexual harrassment comments a thumbs down. The supervisor may be a creep and his actions in hitting on his subordinate may not be the wisest thing for him to do (both for himself and for the good of the workplace) but in order for his actions to be sexual harrassment, by definition, they have to be unwelcome, and in the case of the LW, we know she welcomes them, because she tells us so. Her reaction to being asked for a massage was to figuratively pump her fist in the air and say, “Yes.” This is not somebody who is reluctantly going along with something that makes her feel uncomfortable (which I agree is a very real concern and a problem). She is thrilled. Yes, she turns him down when he asks to go further, but it seems like she does so because she is in a relationship (or because she doesn’t want to seem “easy”) and not because she doesn’t want his advances. This silly young woman may be setting back the fight against sexual harassment by years, but her boss is not sexually harassing her.

  • TheOtherMe August 22, 2011, 9:28 am

    I agree that you should leave your boyfriend but NOT for your supervisor. You’re not happy, do yourself a favor and MOA.

    Also, as Lindsay ˆˆ says, buying a condo has nothing to do with not wanting to start a relationship. Maybe he senses your attraction for him & that’s why you’re always the one he goes to for anything (work related) because he knows you’ll do anything (work related) for him.

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    • Kate August 22, 2011, 9:30 am

      Agree – that line about not being able to date because he’s buying a condo is a big red flag. Translation: “I know you’re attracted to me and I want to take advantage of that by messing around with you, but I definitely do not want to date you.”

      A guy who wants to date you asks you out on DATES. He doesn’t hang out after work and try to get you to hook up with him.

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        fast eddie August 23, 2011, 8:55 am

        Dump the deadbeat boyfriend and keep the relationship at work on a professional basis. You can be friends at work and still be professional. If you BOTH want to go beyond that fine but keep it separate. A no consideration roll in the hay is a very bad idea for anyone you work with and he’s your boss making it asking for trouble in spades. On the other hand Bill Gates married his secretary so who’s to say it has no chance to work.

  • bluesunday August 22, 2011, 9:28 am

    Yes, leave your deadbeat boyfriend who cheated on you.

    No, your supervisor’s not waiting to make your his girlfriend OR keep it platonic. He’s looking for an easy, non- committal office fling.

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  • PFG-SCR August 22, 2011, 9:30 am

    These are two different questions really – the first, “Should I dump my boyfriend?”, and the second, “Should I date my supervisor?”

    To the first, you’re clearly not happy, and the relationship doesn’t sound healthy from the little you’ve shared. It sounds like you not only know you should break up with him, but you want to, so “Yes, dump your boyfriend.”

    I find it concerning that you think you need someone “waiting” before you dump your boyfriend. That indicates to me that you don’t want to be alone, and that’s likely the reason you’ve stayed in a relationship for so long that isn’t happy and healthy. So before you start dating the next guy, work on yourself and your self-esteem.

    Your supervisor has made it clear that he’s looking for something casual, which you know since you included, “He’s not looking for a relationship because he’s concentrating on buying a condo and setting himself up first, which I respect.” I think a casual sexual relationship with your boss under the circumstances will be setting yourself up for hurt feelings and drama at work.

    So, break up with your boyfriend, work on yourself and keep your relationship with your boss strictly professional.

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    • PFG-SCR August 22, 2011, 9:36 am

      There were no comments posted yet when I wrote mine (and I assume it was the same for everyone else because these all were posted so close together) – the fact that we all have stated the exact same advice should speak volumes to the LW.

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        katie August 22, 2011, 8:46 pm

        we can only hope… lol

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    Elizabeth August 22, 2011, 9:32 am

    Very glad to hear that you’ve come to the realization that you deserve better than your boyfriend, but don’t fall back into a bad relationship situation by going out with your supervisor! First, as your supervisor there are some ethical questions with dating you. Second, uh back massage.. creepers. Isn’t that what college guys tried to pull to get girls in bed with them? The ‘you deserve better’ mantra isn’t just a one time thing; it’s a constant message you must remind yourself of! Live it, girl!

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    Lanchik August 22, 2011, 9:33 am

    “I’m currently unhappy with my relationship…”

    Out of your entire letter, this is the line that matters the very most. If you are unhappy and feel like your relationship with your boyfriend has reached a brick wall, then it’s time to MOA.

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  • The_Yellow_Dart August 22, 2011, 9:34 am

    Dumping your boyfriend sounds like a no-brainer – “He doesn’t work, is verbally disrespectful towards me, and jealous because I lack trust for him” – yikes! And above all, you say that you are unhappy, which, in itself, is a good enough reason to end a relationship.

    However, if you break up with your boyfriend, that does not necessarily mean you should begin dating someone else right away – especially your supervisor! Dating your supervisor is like playing with fire. (Have you heard the saying, “don’t shit where you sleep”?) Sure, there are some success stories of people who have married their bosses and lived happily ever after, but these are usually overshadowed by stories of people who have had brief flings/relationships with their bosses, and after those ended, have been uncomfortable in their workplace environment. Jobs are so few and far between these days, so do you really want to put yours at risk? If your supervisor has already told you that “He’s not looking for a relationship” right now, your chances of this ending well (i.e. “I want the next man to work for me”) do not sound very good.

    Instead of dating someone else right away, consider working on yourself and your own happiness. It can take a long time to recover from a four-year relationship, especially an unhappy one. Find a new hobby, hang out with your friends, learn more about yourself (people change a lot in their early 20s)! And if you still really want to start dating again, try to look outside the office…

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  • Maracuya August 22, 2011, 9:34 am

    What everyone else said. You should leave your boyfriend because he’s a jerk, not because some other more-put-together-by-comparison guy seems interested in you.

    Quite frankly, his reason for not wanting a relationship is lame. Plenty of people have bought property while in a relationship. It means he wants something casual, and he’s happy to have you be that person. Get out of your relationship, but don’t muck up the office environment by hooking up with this guy.

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  • fallonthecity August 22, 2011, 9:40 am

    First things first: dump your boyfriend before you even start worrying about your supervisor. It sounds like you are over that relationship. It also sounds like you’re living with your boyfriend, and if that’s the case, it may take awhile to get free and clear of him. Trust me, it’s always a huge drama fest when you try to start a new relationship before you’re completely out of the old one… and it would be complicated enough dating your boss.

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  • TheOtherMe August 22, 2011, 9:51 am

    Also, after asking you for a “back” massage, he showed you his boner and suggested you “do something” ? that part is not super clear for me but still seems totally inappropriate.

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    • PFG-SCR August 22, 2011, 10:03 am

      Her explanation of that situation was confusing, especially what her intentions were – she thought it was her big chance, he tried and she rejected him because she’s not that kind of a girl, and then she was upset with herself.

      These mixed messages seem to be that what she wants her “big chance” to be is not something (strictly) sexual, as much as she’s looking for something more emotionally fulfulling. What he wants to “fill” is anything but emotional…he sounds like a cad.

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      bagge72 August 22, 2011, 11:20 am

      Yeah, and I would also like to know where they met outside of work were it was appropriate to give him a massage, and for him to wave his boner around, and no one would care?

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  • mel August 22, 2011, 9:53 am

    It’s obvious that you should leave your boyfriend. And I think you know that, and you’re just asking our permission. You have mine, just go.

    Girls, you don’t ever owe anyone when it comes to personal relationships. If you’ve been a friend with someone for 6 years, if you’ve been in a relationship for 10, etc, doesn’t matter. If it’s not working for you, if the bad outweighs the good, if you feel like leaving is an option and you want to pursue it: you have every right to give yourself permission to leave.

    Now, keeping in mind that you don’t ever owe anyone anything:

    Leave the supervisor out of your decision. Because guess what? He doesn’t owe you a girlfriending once you’re available, just because he gave you a massage and got a boner once. And that excuse about buying a condo is him, in his own words, telling you that he’s not looking for a relationship. If you want to flirt, and have a crush on him – that’s fine. It might be a nice distraction while you’re going through your breakup.

    And really though… the reason you have this all-consuming crush on your supervisor is because you’re unhappy in your relationship. It in no way speaks to your ability to have a relationship with this supervisor, it’s just your brain telling you that “HEY, LOOK, OVER HERE. THIS IS WHAT A BOY MAKES YOU FEEL LIKE WHEN YOU’RE HAPPY! SEE. LOOK.” Especially since he just doesn’t seem THAT into it.

    Take some time off from relationship drama, and take care of yourself 🙂

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    • demoiselle August 22, 2011, 10:25 am

      He didn’t even do something “generous” like give her a massage. He asked for one and got his kicks from it, then tried to get further satisfaction. Not necessarily an indication of a bad person, but it is notable that he’s her boss and at every step of the way he was looking for how he could get her to give HIM pleasure and not the other way around. IE, he’s looking for his jollies, he’s not primarily interested in her as a person or a potential girlfriend.

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      • mel August 22, 2011, 10:54 am

        100 percent agreed

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    caitie_didn't August 22, 2011, 9:56 am

    First things first, your supervisor sounds creep-tacular. He doesn’t want to date you; he wants to abuse his position of power over you to have a fling with a hot chick and he’ll ditch you once that happens. You say you are 24, but I get the sense that you’re incredibly naive if you think dating your work supervisor is a good idea (trust, it’s not) AND that he actually wants to date you (he doesn’t, unless he takes you out on a date. “Hanging out” isn’t a date”).

    Secondly, yes, you need to break up with your boyfriend. End of story.

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  • Morgan August 22, 2011, 9:56 am

    I feel like we just had this question, but with an mcat tutor instead. My answer remains the same:

    Dump the boyfriend. Don’t date the supervisor. Take some time to be single. Also, dating your supervisor is almost always a bad idea.

    Also he sounds like a creeper.

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    • Maracuya August 22, 2011, 10:06 am

      Yeah, the key difference–instead of being a total creep, the MCAT tutor *asked her out on a date.* Like normal people.

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      • Morgan August 22, 2011, 10:10 am

        Oh yeah, he actually seemed like a decent guy, if the LW had been in any position to date him. This dude….oy. He reminds me of my old boss, in a “likely to appear on the nightly news” sort of way.

    • MsMisery August 22, 2011, 10:15 am

      This is pretty much what I was gonna say. And it seems like this should have been titled two questions: “Should I break up with my boyfriend?” (yes) “And should I date my supervisor?” (no). Sounds like the supervisor is taking advantage of his position and/or the LW’s vulnerability.

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    • Morgan August 22, 2011, 11:20 am

      Also, next time a guy hits on me, asks me out, whatever, rather than my standard “I’m sorry, I’m currently seeing someone” line, I’m going to go with “I’m sorry, I’m currently buying a condo.”

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      • SpaceySteph August 22, 2011, 2:02 pm

        Hah I should have told that to my boyfriend a year ago, because we started dating when my house was under construction. Obviously I should have concentrated on buying a house instead of dating him.
        What does your living situation have to do with your relationship availability unless you are living…
        a) in a crack den
        b) with your wife and kids/lover/girlfriend/mother with whom you have an inappropriate relationship a la Harold from BBT
        c)in a refrigerator box under the freeway

        LW, if he wanted to date you, he would not let his condo stand in his way.

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    bagge72 August 22, 2011, 10:32 am

    So many problems with what is going on at work, and with your boss. You find it OK that your BOSS asked you for a back massage, and shoved his boner at you to let you know how “happy” he was with it? You honestly think that if a guy really wanted to date you he would tell you that right now really isn’t a good time, because he’s buying a condo? Would you be ok with the ugly fat guy from working asking you for a massage, and showing you how big is tent is?

    You asked “How do I know if he’s waiting to be set up to make me his girlfriend or if this is strictly platonic?” You know that he doesn’t want to be in a relationship with you, because he told you so, and I can tell you with 100% accuracy that he is only looking for sex, or he wouldn’t have given you that lame ass excuse after trying to get you to massage his peepee!

    This is also a classic line from this letter “but I’m not that type of girl.” you said this after you thought it was your big chance to hook up with your boss, gave him a massage, and stared lovingly at how happy he was. You have a boyfriend! Guess what you are that type of girl. If you weren’t none of that would have happened with your boss, and while you were in a relationship.

    There is more I want to say, but I’m hoping Sarah, and BGM can say it better than I would be able too.

    Oh and DUMP YOUR BOYFRIEND he sounds like and ass, and you deserve better. Just don’t think better is going to come from your boss! Give yourself time, and meet somebody with the qualities you are looking for, who wants to be with you, and who wont get you fired just for being with him.

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      bagge72 August 22, 2011, 11:12 am

      I also have a feeling that we wont get an update on this one. She is going to take the advice, and dump her boyfriend, and she has already made up her mind that she is going bang her supervisor. Unfortunatley she is going to find out the hard way about what that does to the office enviroment. Guess who’s not going to be the go to girl (for work) anymore once he’s done getting his rocks off? It’ going to be the next hot young girl. Don’t let it bother you though, because if he sees that you are upset about it, he will probably just fire you.

      Also does this remind anyone of the Seinfeld episode where she was sitting in the guys car with him after her date, and without telling her he just pulled out his dick, and expected something to happen?

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      • Maracuya August 22, 2011, 11:16 am

        It kind of reminds me of Sarah’s worst date ever story.

      • TheOtherMe August 22, 2011, 11:26 am

        He took “it” out !!



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        bagge72 August 22, 2011, 11:32 am

        Haha love it! It’s a classic!

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        Budjer August 22, 2011, 11:13 am

        0% of the time….that works every time.

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      katie August 22, 2011, 9:06 pm

      “showing you how big is tent is”

      haha this is my new favorite phrase

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    Budjer August 22, 2011, 9:40 am

    As ALL other commenters have indicated you should never end a relationship only because you have another guy lined up…you should end it because you are unhappy.

    Even though your bf sounds like a dirt bag, I don’t don’t think you acted appropriately in this situation. The guy seems to me the type to let that managerial crap go to his head “commands attention in a room” is what stands out to me – keep in mind your co-workers are PAID to listen to this guy so don’t let that image go to your head. I agree with the advice up above….keep your work relationship professional and try the single life for a bit.

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  • Jena August 22, 2011, 10:41 am

    “I’m currently unhappy with my relationship”

    sooo yeah, even if you don’t jump right into bed with your supervisor, you should get out of your current relationship.

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  • MiMi August 22, 2011, 10:49 am

    Woman, are you cracked? You’re thinking about replacing your using, no-good lout of a boyfriend with an advantage-taking no-good lout of a supervisor who won’t even bother to pretend that he wants more from you than a lay? That’s downgrading from shittier to shittiest!
    You may be yearning to be with someone you admire and respect, but you don’t get there by acting in a suggestive manner and giving your boss such excellent massages that all the blood rushes to his other head! You want admirable? BE admirable! You want respectable? BE respectable!
    Leave these two losers in the dust, and with your attitude and behavior, be just the kind of stand-up, great person you want to attract.

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    • Vathena August 22, 2011, 11:11 am

      This is awesome. Couldn’t have done better myself.

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    • TMSC August 22, 2011, 2:56 pm

      yes, this. I have no sympathy at all for this LW. She created this entire scenario for herself.

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  • moonflowers August 22, 2011, 11:07 am

    I may be reading all this wrong, but the one thing that jumps out at me from this letter is a serious lack of honest, healthy self esteem.

    People with real self esteem don’t stay with an abusive cheating boyfriend – they know they do not have to put up with drama and jealousy and pain just to be “loved.” People with good self esteem also don’t fall hook line and sinker for overt displays for attention like the supervisor’s (raring ambition, commanding attention), because they know that folks with real confidence don’t need the ego boost from constantly show others (and themselves) that they’re big shots.

    The lines “the man I deserve” and “I want my next man to work for me” could be signs of someone who is insecure and lacks true self esteem, putting on a facade of being super go-getter and self-assured. No one on earth “deserves” anyone’s love; all love must be justified by actions and words – and that goes both ways. Likewise, why do men have to “work for” her and not vice versa? Both partners must contribute to make a relationship healthy. Saying these things sounds almost like LW doesn’t believe she could bring anything to a relationship or be worthy of being loved just for who she is.

    LW, take the time to be single and figure yourself out. If you are always with a man, you will always be afraid that you can’t live without one, because you will have never tried it. Confidence is built from experience. It may be a tough slog at first, but the insight you get from knowing yourself better will be a big help in all areas of life, and it will give you the self esteem you need in order to value yourself appropriately and choose partners who will also value you.

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    • kate August 22, 2011, 11:11 am

      I think you’re reading it all right.

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    • SpaceySteph August 22, 2011, 2:05 pm

      I agree. The fact that her boyfriend being a deadbeat and a cheater didn’t cause her to leave him until she found what she percieves as a new and better possibility smacks of someone afraid to be alone.

      Dump the guy because he’s not what you want, not just because you’ve found a new guy to latch on to. Spend some time by yourself until you learn that you can leave a relationship because its not working for you, without waiting until the next best thing is available.

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      katie August 22, 2011, 9:08 pm

      there are so so so many people in this world that need to read this.

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    Landygirl August 22, 2011, 11:07 am

    Quickly make your current boyfriend your ex boyfriend.

    Also, never EVER poop where you eat. Your supervisor is a creep who knows no boundries. You’re so desperate to make a change that you don’t see that you’d be going from the frying pan into the fire.

    Until you learn to love and respect yourself, you will always choose the wrong guy, so first take time to figure out what you want and what makes you happy that doesn’t include being someone’s girlfriend.

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  • SourGrapes August 22, 2011, 11:34 am

    The line that stood out to me the most was the last one – “How do I know if he’s waiting to be set up to make me his girlfriend or if this is strictly platonic?”
    Girl, the answer is neither. Your supervisor (inappropriately) wants a casual sexual relationship with you, and he’s being perfectly clear about it. The fact that you’re approaching the possibility of a relationship with your boss as “girlfriend or bust” screams that you are seeking an emotional investment, which I guarantee will not be reciprocated by your boss. Whether you’ve checked out emotionally from your four-year relationship or not, healing from a breakup takes time. You need to figure out who you are as an individual, and what you need next time around from a relationship, before you can be in a relationship again – especially one that’s healthy. While your supervisor has the qualities that you deserve, like honesty and ambition, he also lacks professionalism and respect for you. Even if this dude wasn’t your supervisor at work, I’d advise against dating him. Whether it’s a few weeks from now or a few months, you’ll be grieving over two failed relationships instead of one. You can do better, and you will do better.. believe that!

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  • meaghan August 22, 2011, 12:02 pm

    You should dump your boyfriend because he belongs in the sewer with the other scum. Leave your boss at the sewage center too until he finds room in his life for you. Why get rid of scum just to pick up toe jam?

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  • LTC039 August 22, 2011, 11:08 am

    Break up with your boyfriend only because you’re dating a dead beat, douche bag, & it’s an extremely unhealthy relationship. Do NOT break up with him because you have a fantasy about some guy that is going to come & “save” you from your boyfriend. Your relationship should’ve ended a long time ago, but it’s understandable why it hasn’t. Look, if you end this relationship & go directly to this supervisor & he breaks your heart (for w/e reason) then you’re going to most likely regret your initial break up, & are not going to see things clearly for what they are. You need to be on your own to process this relationship & heal.

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      bagge72 August 22, 2011, 11:16 am

      Yeah if you have had a boyfriend for 4 years, and people still think your single, I think it’s time to actually be single.

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        bagge72 August 22, 2011, 11:27 am


        sorry to any of the grammar all stars.

      • LTC039 August 22, 2011, 12:27 pm

        Yupp. Why even suffer through that madness of a relationship, if you, yourself are hiding it? Obviously you know that it’s not good. Life is too short for that shit.

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    Jess of CityGirlsWorld.com August 22, 2011, 11:15 am

    LW, please be careful. You have a chance here to greatly improve your life and also a chance to blow it up into a situation far worse.

    Leave your boyfriend because he is no good to you or for you. But do not jump into the arms of another man who is also totally wrong for you. Why is he wrong? Firstly, he is your boss. A relationship with your boss is going to ruin your work environment because sex and work do not mix. Secondly, the type of guy who commands attention when he walks in the room, who flirts with his supervisees, asks for massages, but doesn’t want a relationship (translation: wants sex with no strings) is NOT going to be a better boyfriend. Well, he’s not going to be a boyfriend at all. He’s going to be your boss that you’re sleeping with –not someone that cares for and respects you. This won’t make you happy. In fact it sounds worse than what you have right now.

    Please, please, steer clear of BOTH of these men and start thinking about the kind of man you want to marry. What are his qualities. I bet you he is not going to be the one flirting at the bar, freeloading of of people, cheating, massaging his employees, avoiding commitment, etc.

    Time to wipe the slate clean and start fresh. Take some time OFF to explore your options. Go on some dates. Try the online thing. Get out with your girlfriends. Think about people you know who are in healthy happy relationships (friends, family, etc). What qualities do those people exhibit? Make a list and start looking for those things.

    You have a real shot here of avoiding another relationship with a jerk. Take your time with that shot and don’t be too quick to spend it.

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  • Bethany August 22, 2011, 12:21 pm

    I would just like to point out that as of right now while I’m writing this comment there are ZERO red thumbs on this topic. That means that everyone who has posted or read these comments agrees that the LW should dump the boyfriend and steer clear of the creepy boss. Not one single person disagrees with that!
    LW, please listen to what every one of us here said/thinks… Dump the BF, stay away from the boss and work on loving yourself for a while. You’ll be much happier in the long run.

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      katie August 22, 2011, 9:10 pm

      your so right- as that even ever happened before? we deserve a metal or something!

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  • Stilgar666 August 22, 2011, 12:33 pm

    MOA boyfriend+creepy supervisor+clueless LW=classic/cliche

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  • Sarah August 22, 2011, 12:48 pm

    Soooo, you’ve been with a cheating loser for FOUR years, and now you’re testing the waters without dumping him first with another asshole who just seems to be interested in clothes on-boner massages. Is that right? This might be because I’m really being insightful or it might be that I have to fast all day for a stupid’s doctor’s appointment and I’m already hungry/crabby enough to choke out a co-worker for their blueberry muffin, but I have to say one thing: this all very stupid.

    Dating a cheating loser for four years= Stupid

    Flirting/boner inducing massaging another guy without dumping bf= Stupid

    Validating said flirting/boner inducing massaging while having a boyfriend by saying the boyfriend is a cheating loser= Stupid

    The other guy is emotionally unavailable, you are actually unavailable, and you’ve also started off your relationship with him by lying to him= Stupid

    You want the next man to “work for you”= Stupid, because you want someone to do all the work to make up for the bf you’ve kept for not doing any. You know good relationships require work from both people, right?

    Believing a guy when he says he can’t date because he wants to buy a condo: Stupid

    Looking at clothed boners as a sign you may have found a boyfriend: Ugggg

    So, what you want to hear is that we all think you should make a move on this dude and dump your boyfriend in whichever order you feel comfortable with. You want us to say that you deserve it because your bf is a loser and you deserve a chance to be happy. However, you’re forgetting about that little thing known as personal responsibility. You CHOSE to have a cheating loser boyfriend for four years. You’re CHOOSING to step in cheating territory (or wish you had) without being responsible enough to dump your boyfriend. You CHOOSE to chase some pathetically unavailable guy (either love only comes to those with condos or he doesn’t want you as a girlfriend) to rescue you from a situation you are pretending you didn’t set up in the first place.

    Please distance yourself from both of these men, and don’t pursue any others until you can find out how you can chose men that are good for you, not settle for whatever comes along.

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      caitie_didn't August 22, 2011, 1:27 pm

      I really can’t get past the whole “he basically waved his dick in my face” thing. Girl…..HE’S YOUR BOSS!! HE WAVED HIS DICK IN YOUR FACE!! WHAT MORE DO YOU NEED TO KNOW?!?!

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    • Mary August 22, 2011, 1:54 pm

      “either love only comes to those with condos or he doesn’t want you as a girlfriend”

      So so awesome.

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    • Theenemyofmyenemyisagrilledcheesesandwich August 22, 2011, 2:17 pm

      “Looking at clothed boners as a sign you may have found a boyfriend: Ugggg”

      This was my favorite comment of the day. Best advice all around.

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    • TMSC August 22, 2011, 3:03 pm

      thank you for saying this…

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      parton_doll August 22, 2011, 4:29 pm

      Thank you so much for pointing out that she was moving into cheating territory too and that her situation with her boyfriend doesn’t justify that.

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      • Maracuya August 22, 2011, 4:49 pm

        Agreed. She was so upset after she rejected her supervisor–not because she almost cheated on her boyfriend but because she “thought she lost her chance”!

  • Greebo August 22, 2011, 12:51 pm

    From your letter, you don’t want to be with your boyfriend. You don’t say you love him, don’t talk about his good qualities, don’t mention future plans together. The relationship is already over in your head, so disentangle your finances, residences and lives. You’ve nothing to gain by delay.

    As for the supervisor…I’m sorry, but this raises a lot of concerns. He’s your supervisor. Most companies forbid romance between management and direct reports for VERY good reason. Even if your company doesn’t, do you really want to do this? Depending on your career, this could cause serious and lasting harm to you both. Even if it doesn’t, so far the interest he’s expressed seems to be physical. It doesn’t sound like he’s asking you for dates or coffee. This could be serial behavior.

    Bottom line: this isn’t either or. You don’t want your current boyfriend. End that. But the boss is dangerous. Take some time off dating, get yourself together and then see where you are. Be well.

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  • ncp August 22, 2011, 12:58 pm

    It takes too much time to thumbs up every comment, so I’ll just say:

    ^^^^^^^^^^^^^^^ What THEY said.

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    bittergaymark August 22, 2011, 1:04 pm

    My advice is to get single and stay single. It appears you love drama. First you date a shiftless loser and now you want to get involved with your boss who has specifically said that he DOESN’T want a girlfriend…Meanwhile, you are already fantasizing about being his girlfriend… Yeah, there’s a real recipe for disaster. Of course he IS “going to buy the condo” when he can get the milk for free… So get single. Stay single. And work on your issues… Trust me, you are so not ready for a supervisor with benefits relationship.

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    • MsMisery August 22, 2011, 1:50 pm

      I wonder if this woman has ever been single for more than a month. After rereading the letter, she strikes me as the type to require a constant relationship, no matter how toxic or unrequited (or imagined).

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      • Theenemyofmyenemyisagrilledcheesesandwich August 22, 2011, 2:20 pm

        YES. That was my impression as well. In which case, the best hope of healthy relationships in the future is some single time to get her head straight both about what she’s really looking for in a partner, and her own discretion when it comes to choosing/settling for one.

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    mandalee August 22, 2011, 2:46 pm

    LW, really?!?! When I read letters like this, I wish I could track you down in real life and talk some sense into you! I get it, you’ve been with a horrible boyfriend for years who you’ve allowed to wreck your self esteem after his cheating and what seems just general loser-like behavior. So, now that your creepy ass boss is paying some borderline-weirdo attention to you, you see that as your way out. WRONG. I was you in my early twenties- I jumped from one long-term crap-tastic relationship to the next, never comfortable being alone. Knowing what I know now, I wish I would have dumped the first loser boyfriend and been by myself for awhile. You need to spend some time alone to realize your worth.

    You say “you’ve had your ups and down like many couples do” and then list cheating, unhappiness, jealousy and lack of ambition as the main qualities of your relationship. Those are not normal long-term ups and downs in healthy relationships. Get out of this relationship, and get a hobby or something, but please do not jump into the bed of your boss. Your love life is already dramatic enough, why on earth would you make your professional life just as bad?

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  • Ladybug August 22, 2011, 3:23 pm

    This is the first DW thread I’ve ever seen with everyone in agreement–there’s only one purple thumb to be seen, and I’m betting that was a mis-click. LW, the entire DW readership in all its diverse, snarky glory is begging to to ditch the loser boyfriend and stay far away from the creepy supervisor. If that’s not a clear sign, I don’t know what is.

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    • Ladybug August 22, 2011, 4:41 pm

      *begging you to*
      I have no excuse other than it’s Monday.

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  • Marie August 22, 2011, 3:50 pm

    LW–your honest thoughtful supervisor shouldn’t be making moves on his employees.The problem with you waiting to be his girlfriend is that it’ll never happened.How do I know this?Because he’s already told you he’s not looking for a relationship.You really should take him at his word.Getting a boner from your massage only means he’s horny;it doesn’t mean he’s interested in you.

    Instead of jumping from one loser(the cheating boyfriend–why are you with a guy who cheated on you?) to another,you should be single for awhile.You should work on being a better judge of character when it comes to men.

    And you should know that its inappropriate to give a guy a massage which induces a boner,while still in a relationship.

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    • beans629 August 22, 2011, 3:57 pm

      And it’s even more inappropriate when that said guy is your immediate boss and has the power to fire you or make your life incredibly miserable at your job.

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      • Marie August 22, 2011, 3:59 pm

        Yes,very true.It would be bad enough if this were a coworker,but her supervisor?Good god,he ought to be reported.

  • cookiesandcream August 22, 2011, 5:47 pm

    LW, when I first read your letter I didn’t think you were being stupid; I just think you’re acting out on your basic need for attention. Everyone has a need for attention, and your desire for attention seems to be hindering your ability to make healthy choices for yourself. I think you’re feeling so neglected and under-appreciated because of your boyfriend that you’re willing to get attention from any guy who’s willing to give it to you. It’s like when someone ends a fast, they’re not going to dedicate a considerable amount of time thoughtfully preparing a healthy meal; they’re going to go straight to McDonalds and order one of everything. LW, the supervisor is like fast food–cheap, easy, and fast but so bad for you in so many ways.

    From the way I see it, I think instead of cutting both the boyfriend and the supervisor from your life all at once, you should just focus on bringing the relationship you have with your supervisor back to one that’s strictly professional. Clearly he just sees you as a potential fling (also I want to add that I’d bet anything that he was waiting to get off company property to make a move so you’d be powerless to file any complaints or sexual harassment charges with the company. Plus he’d easily be able to spin anything you say into a lie and say, “She came onto ME!!!” and not face any consequences. In the meantime, you could easily get fired for inappropriate conduct). From now on, I’d recommend not talking to him unless you really have to and keeping your conversations strictly business. If he questions your behavior, you don’t owe him any explanation whatsoever! Have a visual reminder with you at all times to make sure you keep on track, such as an unpaid bill (so you see what you have to lose) or a string tied around your wrist. If he texts or calls you on your personal phone, you can even change the name to something like “Keep it professional” or “I could get fired–be careful.” Do whatever works for you. Then once you have that situation under control, you’d be able to focus more on the issues you have with your boyfriend.

    I know this is getting long, so I’ll wrap up with one final suggestion: therapy. A therapist will be able to guide you in your choices and discuss why you’re making the decisions that you’re making in a non-judgmental manner. It might take some work to find a therapist that’s right for you, but it’ll be so worth it to have someone there who’s 100% on your side and can help you get to the decisions that are right for you. All in all, I wish you the very best and I hope that in some time, you’ll be able to look back at this letter and say, “I WROTE THAT?!?!?! Damn!”

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  • WatersEdge August 22, 2011, 5:54 pm

    I’m gonna give you some practical advice.

    1) Yes, dump your loser boyfriend and hold out for someone better.


    2) Your supervisor is not looking to date you, he’s looking to fuck you. And then stop calling you.

    The right guy will be interested in taking you on a date and giving you a back massage, not inviting you over to his place to give him one. I mean, come on. Did he even order in a freakin pizza?! Plus, he already managed to tell you that he’s not looking for a relationship. If he’s telling you that outright before you hook up, he’s DEFINITELY not interested in dating you.

    My advice theme this week is book recommendations. You need to read Why Men Love Bitches.

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  • WatersEdge August 22, 2011, 5:57 pm

    PS- Wendy… too easy!

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      Wendy August 22, 2011, 6:06 pm

      Well, that’s why I made it a “Your Turn”! But don’t worry; I have a challenging Your Turn lined up for Thursday. Stay tuned.

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      • WatersEdge August 22, 2011, 7:31 pm


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    katie August 22, 2011, 8:46 pm

    ok, from your first paragraph- yes, dump your boyfriend. you obviously aren’t happy. you wouldn’t have written into DW if you were happy. he seems like a loser to me.

    as for your second paragraph- DO NOT get involved with your boss! that is just a recipe for trouble- all the time. ESPECIALLY a weirdo boss who asked for a happy ending after a massage. i can get behind the massage part- i honestly can. one of my co-workers will rub my back sometimes when it is hurting me. now, this is my coworker though, not my boss, and it has never even gone near sexual territory! he is honestly doing me a favor because i am in pain. a boss that is asking for happy endings is going to end badly, i dont care who you are or who you work for or whatever. just. dont. do. it. please!!

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  • Gothic Kitty August 22, 2011, 11:28 pm

    Miss Understood is a slag who needs to be dominated. As she says, she deserves to be used by her supervisor. She should let her current boyfriend go and become her boss’s toy, like she dreams of. It’s everything Miss Understood deserves out of life.

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  • Vinny B. August 22, 2011, 11:50 pm

    You should find out first if the supervisor is a Republican. He sounds like one. If so, avoid him like the plague. As for the boyfriend, he sounds like a victim of a george W. bush and has been disheartened at job searching. Give him a break.

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  • Tomcat August 22, 2011, 11:51 pm

    Sounds like the supervisor wants to give Miss Understood a position on his staff…

    Anyway, agree with everyone else here – dump the loser boyfriend. Do not date or even have sex with the supervisor.

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  • Lee Reynolds August 22, 2011, 11:53 pm

    Before you can have a healthy relationship with someone else, you have to get your own shit together.

    Dump your boyfriend, get your own shit straight, and then MAYBE consider looking for someone else, making very sure that the person you choose to be with also has their shit together. Your boss doesn’t qualify. Any man who isn’t looking for a relationship but is willing to flirt with someone whom he has professional power over is BAD NEWS. At best he wants to have sex with you with no strings attached. At worst he has power trip fantasies in which you are his physical and emotional plaything. Stay away.

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  • El Presidente Castro August 23, 2011, 12:11 am

    Dump the boyfriend for you, then figure out who to date next.

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  • Dave August 23, 2011, 12:12 am

    The correct answer is (c.): none of the above.
    Your bf is a loser.
    Don’t date your boss unless you find litigation and watching future job prospects wither away enjoyable.
    Don’t date men who ask for massages from strange women and then make no attempt to conceal their boners.
    Don’t date men who think you’re single when you’re not. You can’t even be honest about who you are, so don’t dupe him into dealing with your crazy.

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  • Kevin August 23, 2011, 12:42 am

    Dump the worthless slacker. And don’t date the supervisor. You don’t have to have another guy lined up. There is nothing wrong with being alone until you find someone who isn’t a jerk or trying to use you.

    It’s not legally sexual harassment unless it’s ‘unwelcome’. Until you tell him to stop and stop doing things like give backrubs it’s not ‘unwelcome’. (This doesn’t mean it isn’t prohibited by company policy…) But you should tell him no and stop going into those kind of situations with him unless you want to be “the chick at work he sleeps with when he can’t find anyone better”.

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  • RhyanShae August 23, 2011, 1:12 am

    LW…I was in a work situation similar to yours. Except I didn’t want my boss, but he thought I did (he was a horrible, cheating womanizer and sexual harasser), and I was his go-to girl for getting things done. Why did he come to me? He knew I’d do it, and he knew I wasn’t a threat to him. His bosses were his buds, and my complaints about all the crap he pulled fell on deaf ears. He was my boss, jobs were scarce, and so I worked my ass off doing what he asked just to get through it. Meanwhile, behind my back, he was running his mouth about how I was the reason things went wrong. Eventually higher ups became smarter, and I was free from him. Oh, he was also a guy that commanded attention when he came into the room. Didn’t mean he was OMG great, but rather, he was an oppressive personality.

    Trust me, if Sally next to you jumped at every opportunity to do what he asked, he’d be going to her. Guys like that love power and how they can puppet you. His bonus here is that you want him, and he knows it, so he’s pushed the envelope to see how far he can get. Don’t think for a second you even register on the girlfriend scale to him.

    Heck, I really want to know how your coworkers think about this boss considering you’re looking at him through those rosy lenses. I could hazard a guess they see him for what he is, even if they’re pretending he’s an okay guy at work.

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  • Purpleslog August 23, 2011, 12:42 am

    “I’ve caught him cheating but…”

    Dump him.

    As for the supervisor, I have no opinion.

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  • ape_escape August 23, 2011, 5:44 am

    “He’s not looking for a relationship…He continues to flirt with me, though. How do I know if he’s waiting to be set up to make me his girlfriend or if this is strictly platonic?”

    1. He is not looking for a relationship.
    2. Therefore, he is not waiting to “make you” his girlfriend.
    3. He flirts with you a lot. You gave him a massage, and he got a boner.
    4. It wouldn’t be “strictly platonic” if either of you even tried. Jeez.

    Add it up. He wants to have sex with you, and that is all. I’m sorry but I think you need the blunt answers. Been there, done that, and girl, just please don’t fool yourself into thinking this guy wants anything more than the culmination of that “massage.”

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    • ape_escape August 23, 2011, 5:48 am

      …..ugh I can’t even leave this alone. Your supervisor ASKED you for a massage, then SUGGESTED you “do” “something,” and he sounds like the sleaziest of sleazes.

      I think you need a self-esteem boost, and I think you might get it if you see that you’re worth more than EITHER of these “men” COMBINED. get out of BOTH situations, for your own sake. please.

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  • Jim Treacher August 23, 2011, 5:29 am

    “Which of these two narcissists should I submit myself to?” Decisions, decisions.

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  • BM August 23, 2011, 6:33 am

    Dump both of them. Lose the boyfriend because he is not what you want, and you are wasting your time. The boss sounds like he just wants to use you for sex. He realizes you are attracted to him because you are obviously sending all the signals, but has clearly communicated to you he doesn’t want you.

    BTW, the condo has nothing to do with it. One can have a relationship and save up for a condo. In case you didn’t get the news this is a horrible time to be investing in real estate in the first place, and will be for another ten years. A condo is just an apartment where the resident has to eat real estate losses.

    Drop the boyfriend. Make yourself available again. Guys who want long term relationships don’t behave like your boss. They express an interest in children, marriage, and actually having girlfriends. Heck this guy doesn’t even want to have an exclusive relationship. Your current boyfriend cheats but just wait till you get together with a guy who’s already expressed a desire to be free to fuck other women on the side. Yes, that’s what he’s told you but you don’t want to believe it.

    Furthermore, you said your boss thinks you are single. I wonder who deceived him into believing that. Great way to start a relationship.

    In addition this is going to totally screw up your career. Did you think about that? Get ready to look for a new job once things go sour, which will be soon after he has sex with you, and finds out you had a boyfriend all along.

    I had a married woman flirting with me at work even though I’m married. Telling me how her husband is inadequate in various ways. I got the hint and it certainly was fun at first because she’s way more attractive than my wife. However it’s became an irritation after a while. Like dangling red meat in front of a dog. Who would want someone who obviously would cheat with the next guy that came along. I told her to cut out the flirting.

    You are obviously at least the kinda girl who will shop around while in a relationship.

    If you disagree and think it is really your “one chance” which I think is nonsense then at least do this smart. Here are the proper steps to pursue this if you must:
    1) Find a new job where you do not work for or with the guy you are interested in.
    2) Drop the boyfriend, and maybe this should be step one. You are already cheating on your boyfriend by hanging out with your boss and giving him back rubs, and lamenting how you missed your big chance. The way you described it you missed your big chance to be “that kinda girl”. You only failed to make your move because you are so insecure.
    3) Do not go to step 4 until 1 and 2 are complete.
    4) Make sure bossy knows a) You are only interested in a permanent relationship. b) Has your phone number.
    5) He’ll call if he is interested.

    If you don’t think that will work then that only argues that he is not the right guy for you.

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  • paul August 23, 2011, 7:02 am

    No! Do not go with your supervisor. Never s*it where you eat. If the office romance goes bad, you’ll lose twice.

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  • 98wythgfvf8d79 August 23, 2011, 8:18 am

    I’d like to know how she is going to get her boyfriend to move out of her apartment.

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  • JDW August 23, 2011, 8:24 am

    You lost me at “buying a condo”. 🙂

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  • anon August 23, 2011, 3:19 pm

    It has already been said here over and over that:
    1. There are a lot of reasons to dump the boyfriend.
    2. The boss seems less than commited to YOU as a person, to say the least.
    3. Your desire to have a new man before relinquishing the old one makes one concerned that you are scared or embarassed (or something) to be man-less.

    One thing I haven’t seen here is this question: Why HAVE you stayed with an obvious loser for so long? No, really, there is an answer.

    He does SOMETHING for you. It might be that you are afraid to be alone. That friends or family will judge you (or you think they will). Maybe you feel that he physically protects you. Maybe you believe that you might not meet a better guy (until recently).

    At the root of a situation where someone does something that looks crazy to an outside observer, like staying with a cheater that makes you unhappy (for years?), one will usually find that the person believes a lie. That they are unworthy of love, that they need to do X to be/feel Y, etc.

    That’s the thing about lies, you believe them and never know you are decieved.
    Your boss is not the right guy, but finding the right guy won’t fix things if you still believe lies.

    You may not be able to find the lies yourself. If not, you need someone who knows you and loves you. By “love” I mean, the real definition of love: someone who will DO what is best for you, even if that is not what is best for them.

    Parents and siblings often fit the bill, but not if they are tied up with the same lies, are fearful, angry, or have an agenda (however well meaning).

    Beyond that, I can only say: The truth will set you free.

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  • skullwork August 23, 2011, 4:11 pm

    Couple of points —
    Your smart ‘ambitious’ boss is a twenty minute conversation with your HR department from having No job, no career, & no condo. At that point he’ll be pretty much exactly like the boyfriend you’re about to dump. Since you have a scorecard for your boyfriend I’d start one with this guy too and I would count this behavior in the creepy, foolish, stupid, BS, manipulative loser column.
    Be careful about becoming the badguy in all this — If your boyfriend was getting back massages from girls he was trying to seduce would you call that cheating? If your co-workers discovered you were the bosses pet you would be the badguy at work.

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    • convexed August 24, 2011, 11:44 am

      Yes. It’s a hard thing to wrap yr head around sometimes, but who we admire sometimes says more about us then them. The qualities you respect in this guy are qualities you want to see and not question, bc you are looking for men to counterpoint yr loser bf. But the evidence is clear: supervisor’s actions ans words are far from honest, admirable, or ambitious. He’s sneakinf around behind company policy, preying on a naive and eager young subordinate, and risking his career and reputation for the thrill of an easy lay. Honest, admirable people do not do this to themselves and others. They act with care, integrity, and consideration. You need to do as others suggested and take time to get to know your own character and how to read that of others. Look to actions when reading people, not swagger, status, or charm.

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  • MarkD December 20, 2011, 9:55 am

    Why would you want to be involved with a supervisor who is headed for the unemployment line? I’m a supervisor and it’s clear that this sort of behavior would be career ending. We have to take training on this every year.

    Relationships with subordinates are off-limits, for very good reasons. No matter how good a job you think you’re doing, anything done for you will be perceived as favoritism. If you want to pursue this, one of you must work somewhere else first.

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