Dear Wendy
Dear Wendy

“Oops, I Cheated”

It’s time again for Shortcuts. For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss cheating, mixed signals, and financially supporting a significant other.

My boyfriend and I met my freshman year of college and we were dating by the next semester. We have now been together for just over two years. He graduated the year we met and moved about 5 hours away. He works long hours overnight, so when he is not working, he is sleeping, and we don’t have many opportunities to talk. The long distance has been really tough on me because he’s not as good at telling me how he feels as he is about showing me.Everything is going along smoothly and seems to be heading in the direction of us being together for a very long time. The only problem is that I am not ready. I miss being a single girl even though that’s mostly attributed to my raging hormones. Did you enjoy/learn from your single life? I want to be with him and I don’t want a relationship with anyone else, but I also want to have fun and enjoy being young while I can. I had been meaning to have this discussion with him when last night I got really drunk and slept with someone else. I know I have to be honest with him. I know I just maybe messed up the best thing that has ever happened to me. I wasn’t ready. Clearly. — Oopsies

Wow, talk about burying the lede (i.e. that you cheated)! Break up with your boyfriend and enjoy the single life you — and your hormones — crave. If you two are meant to be together, you’ll have a much better chance at a successful relationship if you wait until you’re ready.

I met this guy about a month ago at church. He gave me his number and we’ve been talking back and forth every day since then (texting, primarily). We talked on the phone only four or five times. He doesn’t call. I don’t want to call him too much to scare him off. Sometimes I text him and all I get is the response “busy.” He doesn’t ask me any questions about me except how my day is. But the next moment he could be calling me a queen. I’m very confused at his signals. Any help or suggestions? Mixed signals suck (not to mention he lives five hours from me). I tried to break up with him and tell him I wasn’t feeling the distance thing and he told me no. So I don’t know if I should just call it quits or am I just being led on. — Tired of Mixed Signals

How do you “break up” with someone you hardly know? Texting does not a relationship make, so there’s nothing to “break up,” and you’re certainly not being “led on” if the guy rarely calls you, doesn’t ask anything about you, and only returns a handful of your texts anyway. Since you live five hours apart and already feel grief over a “relationship” that never was, just save yourself the drama and MOA.

I have been with a man for five years now, and though we’ve had our ups and downs, we have learned through the years how to communicate well and respect each other as best we can. He says he feels close and comfortable with me and I return that feeling for the most part. The main issues are his 7-year-old son whom he has every weekend, and of greater impact lately: money. As I have a salary job and he owns his own contracting business that has had leaner times for several months now, I tend to pay for most things like vacations and going out, but then am mad at myself afterwards. At Christmas, I paid for everything at a big party we gave (his other two grown daughters came by) – wine and food all paid by me. I bought him a dryer when his broke down. I have been paying for his weekly groceries for almost two months (which are $160.00 a pop), and loaned him $1,000 to pay some bills last month. Also, I have taken him out to dinner many times in the last few months – on the random Friday night that I see him — as something fun for us. I am obviously sick of spending so much of my money and have told him this. He understands and is trying his best to find work. I don’t want to let him starve of course, but what am I to do if this continues? Should I just leave him? I feel bad about the whole thing, but feel I can’t keep throwing my money towards his needs, while I would rather be saving my money. I would really love your advice. — The money Pit

Quit enabling his financial dependency on you!! He’s a grown man and father of at least three offspring, so surely he can figure out how to pay for necessities, like his own groceries. And for the non-necessities, like dinners out, vacations, and a dryer in his home — I mean, seriously, has he never heard of a laundromat? — you need to let your boyfriend fend for himself so he’s motivated to make a living.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter.

39 comments… add one
  • ReginaRey March 30, 2012, 9:10 am

    LW 1 – There is nothing worse, NOTHING, than continuing to stay in a relationship, and perhaps marrying that person, when you’re constantly nagged by “what if.” Do you want to know what happens when your doubts get to you? You end up cheating. Which, oops, you already did! The only way you relieve the doubt and get the experiences you’re craving are to break up with your boyfriend and be single. Trust me, being single and getting to experience all of the things you’ve been guiltily wanting for some time now is what’s best for you AND your boyfriend — Since he shouldn’t have to be in a relationship with someone who has such consuming doubts; not to mention he deserves faithfulness just as much as anyone. It’s not wrong to feel the way you’re feeling — But it WOULD be wrong to continue on in this relationship given the thoughts you’re having, and given that you’ve already acted on those thoughts. Enjoy your single life, and pronto.

    LW 2 — Yeah, the best way to cut ties with this guy is simply…stop responding to his texts and calls. He doesn’t seem all that into it, and it seems to be causing you more grief and confusion than happiness. And also — When you try to cut ties with someone and they say “no,” that really shouldn’t change your determination to go through with it. I’m a bit worried that you were so easily swayed…maybe it’d be best for you to explore that so that you have more confidence and discerning ability when the next guy comes along.

    LW 3 — The most telling part of your letter, to me, was “He says he feels close and comfortable with me and I return that feeling for the most part.” For the most part? So you only feel…partially close and comfortable to him? Is that because you’re tired of footing his bills? Or could that feeling perhaps be reflective of more? Listen, either way, it sounds like you’ve grown rather resentful of having to support your boyfriend. Stop supporting him, tell him you aren’t going to be able to do it anymore, and stick to your guns. But know this — frustration and resentment often breed contempt. And contempt is pretty much a universal killer of relationships. So if you find that you’re feeling contemptuous of your boyfriend…maybe because you feel like his mother, which isn’t very romantic or sexy…then do yourself a favor and go find someone who you won’t have to support in that way.

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    • kittyk March 30, 2012, 10:45 am

      I think you missed the point of ‘shortcuts’ RR 🙂

      Just giving you a hard time, your advice is pretty spot on as usual.

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      • ReginaRey March 30, 2012, 10:47 am

        Haha! Being brief has never, ever been a strong suit. I’ll leave the real ‘shortcuts’ to Wendy! 🙂

  • Leah March 30, 2012, 9:28 am

    LW1: your only mistake was not ending this relationship sooner. And besides, what relationship? You never see the guy, not for a fun time and not for emotional support, and you’re not even interested in anything serious now anyway! So go see him in person ASAP (seriously, drive up this weekend) and tell him you want to end it because the long-distance is too hard and you just want to be single for a while. And DON’T tell him you cheated! It would just be putting salt in the wound and the only reason to do it would be to absolve your guilt, which isn’t fair. Think of it as the final nail in the coffin of an already dead relationship and try to be a little more honest with yourself, and your boyfriends, in the future.

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    • Renee March 30, 2012, 10:36 am

      “And DON’T tell him you cheated! ”

      If you do he can go around telling everyone, that you’re a slut/whore.

      “Oopsie. I cheated, but I didn’t mean to” is the female version of a fade out. You already moved on without letting the other person know, or yourself in many cases.

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  • TECH March 30, 2012, 9:36 am

    LW3, I know you care for this man immensely, and I’m sure you care for his children as well, but you cannot continue to be his personal ATM! If he’s a contractor who is having trouble finding work on his own, he needs to go and work for someone else for a while. You say that he understands and is trying his best to find work. How many jobs is he applying for per day? How hard is he really trying? If he was really motivated, he’d accept a job at McDonald’s to provide for himself and his family. Also, if the situation is that bad (ie he has no money) he should be going on food stamps. Listen, there are plenty of people in this economy who are having trouble paying their bills, but are able to make their lives work without tapping their girlfriends for resources. Next time he asks you for money, no matter what it is (a new dryer, or a loaf of bread from the grocery store) just explain to him very simply that you cannot continue to hemorrhage money for him any longer. Explain to him the next time he asks you for money, your relationship will be over.
    IMHO, a man with an ounce of self-respect will not ask his girlfriend for money at every turn. He will take responsibility for his own life.

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    • cporoski March 30, 2012, 11:04 am

      I think you are being harsh on this guy. The LW has been in this relationship for 5 years. If they were married, it would be “our” money and it would be tight for both of them. I think she is paying for him to join her on things SHE enjoys. She wanted to throw a party and go on vacation and go to nice dinners. If he went and got a job at McDonalds, he wouldn’t be able to give estimates or pick up quick jobs that a contractor does. I think the LW needs to have a conversation with him but I bet he didn’t ask her for 1/2 the stuff she is giving.

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      • Michelle.Lea March 30, 2012, 1:23 pm

        that’s what I was thinking. you guys have been together for 5 years and you’re having issues helping him?? I get that not everyone thinks that way, but if at 5 years you’re not living together and sharing things already, maybe it’s just not meant to be.

        However, it’s a balancing act to make sure you’re not enabling. and you have to watch out for depression – is that what’s making it harder for him to find work?

      • Monica M April 2, 2012, 12:55 pm

        I agree the 5 years part is the big issue. I wish she would have addressed why they have not merged more as a couple. It is hard to not be sexist in analyzing this situation, because I think if the roles were reversed it would not be perceived the same. I think the LW needs to really analyze her whole relationship and figure out what she actually wants. From the letter she says this money thing is new, which is a minor and maybe temporary problem. However, if the money issue has always been there then she needs to rethink what she wants in a partner.

  • kerrycontrary March 30, 2012, 9:36 am

    What stuck out to me with LW3 was that one of their biggest problems is “his 7 year old son who he has every weekend>’ If you aren’t ok dating someone who has kids, then don’t date someone who has kids. You aren’t just dating your boyfriend, you are dating your boyfriend and his kids. It sounds like the LW isn’t seeing her boyfriend on the weekend because of his son. Does she not like doing things with kids? And lastly, if you don’t want to pay for everything for a huge holiday party then don’t throw a huge holiday party! It seems like the LW is mixing up “wants” with “needs”

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  • 2_J March 30, 2012, 10:06 am

    LW1 – MOA! What bugs me is that you didn’t just come out and say ” hey i screwed up and cheated”, you HAD to throw in the “i got really drunk” and slept with somone. Being drunk is never an excuse, you knew what you were doing, take full responsibilty for the decision you made.

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    • Anon March 30, 2012, 1:08 pm

      I also noticed the excuses made for the cheating! “I have these absolutely RAGING hormones” and “I got really drunk…” LW1, just come right out and own up to it: you cheated. You chose to do it. So stop trying to justify “why” you cheated.

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  • bagge72 March 30, 2012, 10:13 am

    LW:3 First thing is what types of problems are you having with his 7 year old son? If it is just him being there, and getting in the way, then I hope he dumps you, because his son comes first, and you didn’t list what the actual problems were.
    2nd you need to do is stop going on vacation, throwing expensive parties, and doing all of the extra things if he doesn’t have the money to do them, it’s hard to survive when you are making less money if you don’t make any life changes at all. What would he do if you weren’t around? I bet he would have no problem paying his bills, and eating then, but you feel like you have to keep him in this lifestyle he has been used to, and he is never going to learn how to take care of himself when times are tough, as long as you keep footing his bills. Also after 5 years maybe you should see if things are ready to progress into something like moving in or getting married so you can start splitting the bills, and things become less expensive for both of you.

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    • savannah March 30, 2012, 10:40 am

      I agree with this and I also question the $160 weekly grocery bill. She says its his weekly bill, not theirs, and with just himself and a 7 year old 2 days a week, does that seem like a high number to anyone else? LW3, where are you shopping?

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      • cporoski March 30, 2012, 11:09 am

        This makes me think that she is used to a different lifestyle than she is getting. If you go to a high end store with alot of fresh food, it is easy to spend this.

      • jlyfsh March 30, 2012, 11:11 am

        yeah i agree if you only shop at places like whole foods, the fresh market, or other small specialty stores, it’s very easy to spend a lot. makes me also think there is a difference in life style there as well.

  • EricaSwagger March 30, 2012, 9:36 am

    LW1 – It’s always sad to realize you might not be as in love with your bf as you think you are. You clearly don’t love your boyfriend enough to sacrifice having a life and having sex when he’s not around. Long distance sucks that way! If you want to make it work, you sacrifice.

    LW2 – You’re very naive to even ask this question. You’re holding on to nothing. I’m sorry, but this guy is not your boyfriend. Grow up.

    LW3 – A man with 3 kids, (two grown, no less!) should be paying for his own groceries at the very least. Man. Maybe I’m old fashioned, but having to take care of a man who clearly is capable of taking care of himself but just wont, is a huge deal breaker. It’s one thing to pay for stuff temporarily (while he’s between jobs, or whatever) but this seems pretty permanent and I’m shocked you haven’t moved on yet. This is just my way of thinking, but I’d rater be someone’s partner (read: EQUALS) than their caretaker. (You’re buying his food and making sure his laundry gets done; you’re his mama.) Idk, maybe that’s just me…

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  • Will.i.am March 30, 2012, 10:44 am

    LW1: I think you wanted to cheat to see if you would feel guilty enough to stay with your boyfriend. You clearly didn’t so now you can MOA. Like someone else mentioned, don’t say anything about cheating. It’s not worth it at this point.

    LW2: This is the second church letter about a guy sending mixed signals. You have nothing here and you are clearly grasping for straws. He probably just took your number to add to his list. You aren’t the only girl he’s texting.

    LW3: You are not his Mama. It’s time to have a come to Jesus talk with your boyfriend. Also, when you are seriously involved with someone who has kids, you are with the man or woman and their kids. If you are on the fence about kids, then mention that up front before you ever go on a first date with anyone. Many different men and women going in and out of a childs life is not very healthy and they can tend to lead destructive lives because of it.

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  • FireStar March 30, 2012, 10:48 am

    LW3 – you said the main issues were money and your BF’s 7 year old. The money thing may be easily solved – don’t give him any. You have a financial obligation to provide for a child – and no one else. And speaking of a child – his son was there when you started dating your BF. I don’t have much sympathy for women who date men with children and then get upset because the men they are dating have children. If his son is an issue for you – then MOA and find someone childless.

    LW2 – There are guys like that that just try and keep you hooked for the attention or to alleviate their boredom or for whatever reason speaks to them. In life – judge a man by his actions not his words. I promise you this rule will save you heartache. Don’t bother replying to any more texts and if he calls you tell him you done…royal titles notwithstanding.

    LW1 – Your hormones aren’t to blame – your choices are. You cheated. Own it. Move on from your boyfriend and tell him you want to see other people. Then cut contact with him so he can move on and find a girl that will be faithful.

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    • Francine March 30, 2012, 4:37 pm

      Well said!

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    • fast eddie March 30, 2012, 3:51 pm

      Ouch! That’s biting FireStar, we have no idea if he’s being faithful or not. A better solution would be to make their relationship an open one so they both have their needs fulfilled.

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      • Francine March 30, 2012, 4:48 pm

        No reason to think he is cheating. FireStar addressed what the lw wrote. We can guess at what else might be going on and come up with all kinds of different solutions to fit those scenarios but nothing wrong with using the info the lw provides and basing a solution on that either.

  • CatsMeow March 30, 2012, 10:57 am

    LW1 – while I’m not proud of this, I was in a similar situation. I was with my very first boyfriend for about a year when I started to get the urge to just be single. I was just… antsy. And I couldn’t understand it because we got along very well, he loved me, we had a lot in common, blah blah blah. I was afraid that if I broke up with him, I would never find anyone better, or anyone who would love me and understand me like he did.

    I let these feelings simmer. I tried to ignore them. I thought I was just going through a phase. And then? I kissed another guy.

    After that, I knew I had to break up with him because if I truly had any respect for him or for the relationship, that never would have happened. So I did, and yeah, it was kinda messy. (For the record: I told him what happened. But you shouldn’t do that. Spare him the pain). While I regret what I did, I do not regret ending the relationship. And I learned from it!

    So, LW1, MOA. Have fun, be single, and don’t make the same mistake again in your next relationship.

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    • cporoski March 30, 2012, 11:11 am

      I once read that when a woman cheats, she has already mentally ended the relationship. That once you are there it is too late.

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      • CatsMeow March 30, 2012, 11:15 am

        Yeah, that was definitely true in my case. And now I know that if I’m having problems or doubts in a relationship, I need to address it before it gets to that point. Sounds simple, but hey, I was 19 and still learning the ropes.

      • Renee March 30, 2012, 11:27 am

        Defintely. LW1 mind was already made up for sometime, well before she started to drink and hook up.

  • Fabelle March 30, 2012, 11:00 am

    Oh, LW1. Don’t feel too badly about cheating, since your boyfriend is 5 hours away & you guys seem to barely even speak. But yes, please break up with him & have your fun being single. You say that you don’t want a relationship with anyone else, but there’s no way of knowing that unless you allow yourself to have other experiences (And, uh…looks like you’ve already begun!)

    LW2: What even–? “I tried to break up with him and tell him I wasn’t feeling the distance thing and he told me no.” He told you no? “No” to what? Did he literally just text back “no”? (From what you’ve described, I wouldn’t be surprised). Maybe his response was actually appropriate, since you can’t end things with somebody with whom you have no relationship with. Stop texting him & he’ll stop texting you, and then you won’t have to deal with any “mixed signals” anymore.

    LW3: Ugh, I kind of got into this situation with a good friend of mine (though not as much money/as often) but a point came when both of us were like “Dude, this is so uneven” & it stopped. It won’t be as simple for you, of course, since you’re in a relationship with this guy, but you need to say something like “This is getting a little out-of-hand.” After you make that statement, don’t provide him with ANY more of your money. If you feel like going out to dinner, go with somebody else. If you’re over and you catch him sighing longingly into his empty fridge, just be like “Aw baby, it’s tough, but you’ll get through it” instead of offering to run to the store.

    As for the bigger stuff you mentioned, he doesn’t need a working dryer or any parties. But that was nice of you. Now stop being “nice” (aka a martyr) & save your money.

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  • Zepp March 30, 2012, 11:22 am

    If LW3 and her boyfriend were married, it would be “their money” and this would be a relatively normal situation. After 5 years they easily could be married so I guess the fact that she doesn’t want to be married to him means she doesn’t want the whole partnership through life/our money for our family/etc. etc. So if that’s not what you want don’t let it happen.

    But I have no sympathy for the 7 year old situation. When you got together he had a 2 year old so you knew what you were getting into. I could never date a guy with kids, there’s no shame in recognizing you don’t want to deal with that.

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    • TaraMonster March 30, 2012, 12:10 pm

      This was my thought too. If she is this resentful over picking up the slack after 5 years the relationship sounds pretty much done to me. And the way she just casually mentioned his son being the issue, without explaining why it’s an issue had me raising my eyebrows. Because if it’s just the fact that he HAS kids that bugs her then she should have dealt with that 5 flipping years ago.

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  • Skyblossom March 30, 2012, 11:29 am

    LW2 The combination of your question, the way you are “dating” and the fact that you don’t feel you can break up if the guy says no makes me wonder if your family is a Christian patriarchal family. I’m guessing that you belong to a family or religion that emphasizes courtship instead of dating and a womans submission to her father and then her husband. If that is the case I want you to know that it is okay for you to have your own opinions and to act on them. It is okay to tell a guy no and mean no. It is okay for you to quit seeing a guy even if he says no. It is okay to question and to make your own choices. Your parents have made decisions that best suit them and their life and as an adult you get to make your own choices about what best suits you and your life.

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    • caffeinatrix March 31, 2012, 4:08 pm

      I caught that too. She said she tried to break up with him, and he just… told her “No” ? If one person decides to end a relationship, it ends. LW2, you have no obligation whatsoever to keep in contact with him if he’s leading you on and not giving you what you want. He doesn’t have veto power with this decision.

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    • Skyblossom April 1, 2012, 9:29 am

      I wonder if you can see yourself in this. If you can I hope it helps a little.

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  • rachel March 30, 2012, 12:19 pm

    LW3, without the money problem you’ve clearly got issues with this relationship. I’ve been with my boyfriend for almost 3 years and I hope after 2 more I can say more positive about our relationship than “we respect each other” and “feel close and comfortable for the most part”. Correct me if I’m wrong, but it doesn’t sound like you’re really even still in love with the guy. And what problems do you have with his kid (who was 2 when you started dating)? It just doesn’t sound to me like you really want to be in this relationship anymore. Which is okay. You can break up with him, even though he’s broke. He’s a grown man, he’ll take care of himself.

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  • Budj March 30, 2012, 12:31 pm

    Kids (right now) would be an issue for me in a relationship….that’s why I don’t date women with children no matter how awesome they may be…

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    • britannia March 30, 2012, 5:09 pm

      I agree. I would never date a man with kids. It’s perfectly fine to have that boundary, but it’s definitely not okay to get into a committed relationship with someone if you aren’t going to welcome, love, and respect their children.

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  • caitie_didnt March 30, 2012, 2:31 pm

    hey, people of the universe? I have a suggestion for you: if you don’t like children, don’t want children and have no interest in having/caring for/raising children? Maybe, just maybe, you shouldn’t be dating SOMEONE WHO HAS CHILDREN.

    Shocking, I know.

    That being said, I don’t really understand the “issue” in LW3’s letter. Is it that her boyfriend has a young child, or that she’s financially supporting her boyfriend? Or is it that she feels she’s also supporting the kid? Well, guess what, LW3- the kid didn’t drop out of the sky one day, he was 2 when you and your boyfriend got together. If it’s the money issue….what Wendy said.

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    • oldie March 30, 2012, 8:10 pm

      It sounds like she doesn’t spend time with bf and kid, at least that’s what I took from comment that whe only occassionally sees him on Friday night, when she takes him out to dinner. THere really doesn’t seem to be much of anything that is beyond ok in this relationship, given how the LW describes it, and much that she finds satisfactory. Why support a bf, and his son on weekends, to be in a relationship that you can only manage to describe as ok. The whole letter sounds like she ‘settled’ for this guy and now is having second and third thoughts. MOA. It is unlikely to improve.

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  • Francine March 30, 2012, 3:05 pm

    Re: LW 1

    “The long distance has been really tough on me because he’s not as good at telling me how he feels as he is about showing me.”

    Seriously? Really? You didn’t tell your bf how you were feeling and then cheated on him. Someone in your relationship is better at showing their feelings than telling them and I’m not sure it’s your boyfriend!

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  • theattack March 30, 2012, 4:12 pm

    LW1: I have been in your situation almost exactly to a T. I was with a guy who was perfect for me, long distance, when I was young and inexperienced with other guys. (I’m only one of those things now, and hinthint: I’m only 22, so….) We were together for a few years, but I cheated on him because I was burning for more experiences but still knew he was right for me and didn’t want to lose him forever. I eventually broke up with him when my frustrations and urges became too strong for me to manage. We remained good friends for three years while both of us grew, experienced new things, and figured out where we were going with life. Now we’re back together (for about two years now), and things are wonderful. We’ve got direction in our lives, and we’re in our relationship for the long run. Neither of us have looked back or wondered about other people since then, because we allowed ourselves to explore things earlier.

    I don’t want to say that it will work out if it’s meant to be, because I don’t think that’s necessarily true. But it might work out for you two eventually if you’re honest with yourselves about what you want now and later. Be honest with each other about what you need now, try to maintain a friendship with him after you end things, and if both of you still want each other later, you can try it again.

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