“I’m Torn Between Two Guys”

I am a woman in my early 20s who is in a (mostly) good relationship with my boyfriend of a few years, “Chris.” While I love him deeply, I’m not sure he’s the “one.” Despite my reservations, based largely on my relatively young age and the fact that there exist certain incompatibilities that are becoming increasingly apparent, I have no desire to leave my relationship in the immediate future.

While I have never cheated on Chris and never would, there is another man in my life. I have known “Jack” since I was 15 and he was in his early/mid 20s. When I was 16, after a few months of platonic friendship, our relationship became more sexual in nature. While it was never fully consummated (we engaged mainly in oral sex) the experience was a profound one as it was my first sexual encounter. He was a family friend and one of my parents was aware there was a romantic connection between us but did know its sexual extent. After several months of this, he moved across the country for a job opportunity. I was completely heartbroken. He was my first love and I have never loved anyone with an all-consuming intensity as I did him.

Fast forward nearly seven years and Jack and I are still in contact. Our correspondence has waxed and waned over the years but we have never fallen completely out of touch. Lately, it has been much more frequent due to the fact I visited him (along with a work associate I was traveling with) while on a business trip near his city a few months ago. Needless to say, it was great to see him after all these years. However, my visit reminded that, like with my boyfriend, there exist certain incompatibilities that I believe would hinder a lasting relationship. I am older now so the eight-year age difference is no longer a problem but his commitment issues (he’s 30 and hasn’t had a real relationship since college), different lifestyle preferences and the fact that I don’t think he could ever truly love me and treat me like I deserve, are.

What complicates all of this is that Jack wants to come up and visit me. My boyfriend was upset that I visited him while on my trip and I don’t think he’d be receptive at all to rehashing this issue. I communicated this to Jack but he contends that he wants to come up mainly to visit the city I live in and my family (who he is old friends with but hasn’t really kept in contact with), not to see me specifically. So I said that I’d try to get together at some point if he made it up but would mainly leave him to his own devices. He then backtracked and said he didn’t want to make the trip up just to be “alone,” but still couldn’t admit that he really wanted to see me. It’s just like he has always said that he could see us being together sometime in the future and that he cares about me, but has never said that he loves me.

So what should I do? My brain tells me Jack’s not right for me but I am unable, and always have been, to let him go completely. I feel so stupid and am immensely frustrated that I cannot turn my feelings off for him, even though I am convinced he doesn’t deserve them. I would love for him to come visit, but I don’t want to jeopardize my relationship with Chris. Should I cut off ties with Jack or continue to maintain a friendship? Am I doing wrong by Chris for feeling ambivalent about the future of our relationship but not ending it because I still enjoy it right now? Please help. — Between a Rock and a Hard Place

I’ll answer your last question first: you are only doing wrong by Chris by staying with him if he doesn’t know your ambivalence about a future together. Despite your young age, after several years together, he may think you’re on a track to something long/life-lasting, and if you know in your heart that that isn’t the case, you owe him the courtesy to tell him so. He’s especially deserving of this information if he’s at any point alluded to wanting/expecting a future with you. If he has, and you’ve let him believe it’s a possibility when you know it isn’t, you’ve essentially led him on, which is not only a cruel thing to do, it’s bad relationship karma. So, I suggest sitting down with Chris and having a conversation with him about where things stand. Let him know how deeply you love him and how much you enjoy being with him and are in no hurry to move on, but you also feel he needs to know that you don’t see marriage in your cards and if that’s something he wants to move towards, then he shouldn’t waste valuable time with someone who doesn’t share that same vision with him. This honesty may cost you the relationship, but in the end, it will save you a lot of drama and heart ache down the road. It will also free you to consider your situation with Jack a little more clearly.

When it comes to Jack, I guess I’m wondering: what’s the point? If you stay with Chris, you’d be making a mistake continuing a friendship with a man you know wants more from you. It’s unfair to Chris, for sure, and it’s unfair to Jack. And you, too, really. Why invest your already complicated emotions into something that isn’t going anywhere? Jack doesn’t want to be your friend; he wants something you aren’t prepared to give him, for a variety of reasons. Granted, you may not be able to magically turn off your feelings for the guy, but I can tell you what will certainly help you get there eventually: dropping all communication with him. Don’t go visit him, don’t let him visit you, and quit sending emails and texts and phone calls. Just MOA. Nothing good can come from continued correspondence with him. You’ll just keep feeling like there’s something there between you but not enough to really make a relationship work, and he’ll keep thinking you’re interested and continue coming between you a successful relationship with someone else (whether that someone else is Chris or not).

So, in a nutshell: come clean with Chris. Give him the courtesy of your honest feelings. And MOA from Jack. Do both of these things and the relationship drama and anxiety in your life with drop significantly — maybe not overnight, but definitely over the course of the next few months.

*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.


  1. The fact that Jack thought it was perfectly acceptable when he was 24 to get a beej from a 16-year-old should be enough to make most sane people MOA from that creep.

    1. lets_be_honest says:

      Beat me to it!

    2. The_Yellow_Dart says:

      This was the thing that stood out the most for me from the letter too – yikes!

    3. That is so true. And he considers himself a friend of the family… At 15 you may have been young and naive and infatuated, but now you should know that that is just wrong.

      1. Addie Pray says:

        Oh and this comment made me remeber something else from the letter: The LW’s mother KNEW about about 15-year-old LW’s “romantic connection” with the mid 20 year old “family friend.” … Sick. The mom should’ve kept him away.

      2. I have nieces who are that age, and if my brothers (I am talking about 2 6′ and 220 lb firefighters) ever find out that some 20-something year old “family friend” is getting BJs out of them, I wouldn’t want to be that “friend”…But then again, that may be a reason why guys were very respectful to me…

      3. Sounds to me like it could have been a typo. “One of my parents was aware there was a romantic connection between us but [not] did know its sexual extent,” sounds a lot more natural to write. Hopefully it’s a typo…

      4. Doesn’t matter. I still would tell the friend to stay the hell away from my 16 year old daughter.

      5. Addie Pray says:

        I gathered that the mom didn’t know about the BJs, but she knew of a “romantic connection” – that enough is sick. I mean if a grown man in his mid 20s is having any sort of romantic connection with a 15 year old that her mother can see/witness/know about – sick, get him away. He’s no family friend.

      6. Addie Pray says:

        Not sure why I assumed it was her mother… she wrote that one of her parents knew. IRREGARDLESS. [I’m kidding, “irregardless” is not a word, but, said with a little ‘tude and disgust, it feels appropriate here.]

      7. lets_be_honest says:

        I’m giving you a hug in my mind right now for saying IRREGARDLESS. From one incorrect grammer hater to another 😉

      8. Not to be rude, but it’s spelled ‘grammar’…

      9. Oops, that’s true. I read your original comment wrong. 🙂 Sadly, there are parents out there who will encourage that thing.

    4. You took the words right out of my mouth. That is CREEPY!

    5. CottonTheCuteDog says:

      Amen to that!

    6. Jess of CityGirlsWorld.com says:

      YES! Also, is my math wrong or was it actually a 15 and 23? Even worse. One has just hit puberty and dreaming of the prom NEXT year. The other is the age of a college grad striking out into his career and first apartment.

      8 years is a tough road for people much older –power dynamics, etc.

      Sure, this guy has a hold on her because of the time and milestone in her life. But he’s no good and she knows it. He may take awhile to shake because those kind of “chemicals” take awhile to dissipate. But as Wendy said, the best way to speed up the process to steer clear of him. Eventually her heart will catch up with her (rational) mind on this subject.

      As for the current BF, harder to say. The gut is usually right. The moving on part is harder to do. Many times the revelation (he’s not the one) comes long before the courage to MOA does.

      1. I think the LW was 15 when she first met the guy, but 16 when they started sexual relations. I don’t think they actually started the relations prior to 16 – otherwise Jackie-boy would be subject to statutory rape, no questions asked. Yet the thought that at 16, she engaged in mutual oral sex with this guy when he was in his mid-20s…that’s a hella creepy birthday present.

        LW – MOA from both of these dudes and figure out what you want in a relationship before you even think of settling down.

    7. I would *mostly* agree with you, but sometimes, just sometimes… there are exceptions. I went to high school with a girl who throughout our high school years was dating a guy at about this same age difference (she may have started dating him when she was 15/16 and he was 22/23?). I remember when I first heard how old her boyfriend was being shocked. But, then we all met & hung out with him. He was always super sweet & a gentleman. Her family did know about the situation… and I think kept him very close at hand, just so they could guard the safety of their daughter. I am not sure at what point the relationship got sexual as I never asked her. But, I always got the impression that he was very kind to her and would never do anything to hurt her.

      And, guess what? They are married today. He treats her very well and it seems to be a very healthy relationship. While if I had a young teenage daughter and she started dating a 20 something, I might kill him… I guess there are rare circumstances where the guy is actually a nice guy and isn’t looking to just take advantage of a teenage girl. Keyword being RARE.

      To the LW- it won’t KILL you to be single. You have strong reasons that neither of these guys are right for you. So, just go be ALONE. Many a girl has survived being single. Thrived, in fact. You’ll learn a lot. It will be good for you. And you won’t be stringing anyone along.

  2. CG took my post right out of my brain – the rest was taken care of by Wendy in the column.

    1. I can’t stress enough though how shitty it is of the LW to be in a relationship with “Chris”. That’s totally not fair – if he had sound clips of the LW’s inner monologues I’m sure he’d be thrilled to stay in that relationship.

      1. Allow me to paraphrase the LW about Chris: “I like him, and we’re comfortable together, but I don’t plan on staying with him once I find something better.”

  3. silver_dragon_girl says:

    There are two completely different issues in this letter.
    1. The LW doesn’t see a long-term future with her bf, but he’s good enough for now.
    2. The LW still has a crush on the “older man” she fooled around with as a teenager, despite the fact that he apparently hasn’t matured emotionally past the age he was when they hooked up.

    As for number one, I’d say read your own letter and it pretty much answers your questions. You don’t sound happy. Believe me, once you’ve decided that the relationship does NOT have long-term potential, it’s only a matter of time until it ends. Wendy’s right, your bf deserves to know that you’ve put a time limit on your relationship with him.

    Now, as for number two…seriously girl, give up. The guys is never going to sweep you off your feet and ride off into the sunset with you. He’s just not. He hasn’t had a relationship since college because he doesn’t want one, NOT because he’s secretly pining away waiting for you to grow up. He’s not coming to your hometown to see you, he’s coming to have a little stroll down memory lane. He’s SO ambivalent about you it’s ridiculous. I agree with Wendy- you need to cut off all communication with the guy. A little distance will do you a world of good in this situation.

    1. He hasn’t had a relationship because he’s too busy moving from town to town befriending families with high school aged daughters.

      1. Haha jack pot! This guy has a problem! How did a 24 year old become friend with her parents anyways?

      2. silver_dragon_girl says:

        Seriously! Creep-tacular.

    2. Yup, he is trying to finally get in those pants, because the BJ wasn’t enough. You can tell that is what he is doing, because he is trying to make you feel bad for him coming to your city and being “alone”. This guys is a smooth talker, he has your whole family to hang out with, and I assume other friends from when he used to live there, though I bet if they knew what he did to you when you were a young child who couldn’t make up her own mind, then I’m sure they would never want to talk to him again.

      1. I enjoy how we both are able to cut through creeper’s words and get to the point.

      2. The joys of being a guy sometimes is seeing right throw other guys bull shit even if the girl you tell it to wont believe you!

      3. It’s a fun mental game of “what does this person have to benefit” which is a lot easier to think about where a guy is coming from when you are a guy.

      4. exactly! Unfortunately I think we might apply this a little to much, but I’m ok with that! Better to be safe than sorry.

      5. haha – speculating is half the fun here 🙁

      6. Dealt with too many of these “guys” to care to mention. I’d rather take them out for “target practice” and leave it at that.

      7. iseeshiny says:

        No, it’s different! Can’t you see? They’re soulmates! Their love is not defined by such petty things as age, it transcends that… stuff. He wouldn’t have paid so much attention to her if she weren’t different, he always knew she was more mature than other girls her age, he made her feel special! Theirs is a love like that of Edward and Bella!

      8. Jess of CityGirlsWorld.com says:

        AMEN. Could not agree more. This is exactly his M.O. Sadly, there are enough guys out there like this, that you can spot them fairly easily over time. They tend to be charming and charismatic as hell too.

    3. Jess of CityGirlsWorld.com says:

      Yes to everything you said here!

  4. Not to totally discount the LW’s feelings, but aren’t most things at 15 or 16 felt with an “all-consuming intensity”? I’m not saying she didn’t love Jack back when, but people change, feelings change, especially in the years she’s talking about. Also, if you’re not sure Chris is the one, leave him alone. Let him find someone who is crazy about him and is 100% sure he is the one. I’ve been led on- I’d just like to warn you that chances are it won’t end pretty. And I’d advise you to cut Jack out of the picture as well. You don’t think Chris is the one for you, and Jack doesn’t sound like he thinks you’re the one for him. And if this is true: “I don’t think he could ever truly love me and treat me like I deserve,” I’m not sure I see what else there is to consider.

    1. I was going to bring up this point to. One thing to remember when comparing your current love to your teenage love, is that teens feel more strongly than adults. This is not because your feelings are more real or important as a teenager, it’s because of physical (hormonal) changes in your body, and the fact that different parts of your brain mature at different rates throughout your teenage years (up to at least 25 years old, actually). Add to that the fact that you haven’t spent any significant amount of time with Jack in 7 years, and your teenage love becomes really irrelevant. You’ve both grown and changed a lot in 7 years, you’re not the same people, so why should the love be the same?

      Add this bit of info to all of the terrible things you wrote about Jack (including that he was a 24 year old who thought it was normal to hook up with a 16 year old). Why would you consider him? Cut off contact.

      1. Forgot to add: you’re not going to find the same all-consuming love you felt as a teenager again – even if you get together with Jack. That level of obsession is not healthy.

      2. ReginaRey says:

        Seconded. When I meet the person I end up marrying, I’d like the love to be deep and passionate, for sure. But all-consuming? No. That was definitely something I felt with my first boyfriend, under the influence of first-time-love. It’s dangerously obsessive, and not healthy. Your love shouldn’t consume everything else in your life. I’ve got a lot of other shit and people I love, too!

      3. lets_be_honest says:

        Under the influence of first-time-love. USING THAT!

      4. Jess of CityGirlsWorld.com says:


      5. Word. There’s a reason Romeo and Juliet were teenaged characters amiright?

      6. lets_be_honest says:

        I’m thumbing you up for your use of the word “Word.”

    2. elisabeth says:

      This! So much this. When you’re a teenager, every relationship feels like it’s huge, like you’re in love, there’s “all consuming intensity,” all of that. She’s remembering the feeling accurately, but as she matures, she’s not likely to feel that kind of passion again, at least not for long.

  5. demoiselle says:

    Ugh to a 24 year old who’d get involved sexually with a 16 year old. No wonder he’s 30 and hasn’t had a lasting relationship. . .

  6. Honey – Jack is a teen crush that you never got to go “all the way” with, and you are still in fantasy-mode thinking “what if” and “what would it be like” about. KNOCK IT OFF. This is a guy who WAITED UNTIL YOU WERE ABOVE THE LEGAL AGE OF CONSENT to be able to have sexual relations with you while he was in his 20s. He knew what he was doing and was a creepy sonofabitch about it. He was not honorable, otherwise he would have been aboveboard and DATED you properly and with full knowledge (and permission) of your parents (since they were FRIENDS). He used you for sexual favors. Period. You were just to naive to know it.

    The guy you are with now is a better match, even if you are still in fantasy-Jack-land. I have no doubt that those incompatabilities are construed so you can continue to fantasize about the coulda-woulda-shouldas of Jack. Again – knock it off. Jack doesn’t have any long-term relationships for a reason. He’s a selfish prick who likes naive girls that will pleasure him. Look at how he beats around the bush when talking to you about his trip. You know what he really wants when he comes to town? Sex. With you. Why? Because he didn’t get it when you were a teenager, and that is an itch he just has to scratch. That’s it. And deep down – you know it, and you LIKE being desired by another guy, especially by a guy that has wanted you for as long as you two have known each other. This fantasy you have, that he has been “waiting” for you (otherwise, why wouldn’t he have had a long-term relationship or two since you were 16?).
    You’ve said there are issues with compatibility. What are they? Other than the creepy advantage-taking?
    Walk away and realize that had you been a few months younger, he would have been arrested for sexual abuse of a minor. Apologize to your boyfriend for being sneaky for meeting the guy behind his back. Either dump your current guy so he can find a less delusional chick or stay with him and get over this chester. Stockholm, thy name is LW.

    1. lets_be_honest says:

      Love the tough love. Haven’t seen an AKChic “Honey” in a while! It baffles me how a now-twentysomething doesn’t realize that he was using her for blowjobs. WTF. Grow up already, or read a book about growing up at least. Jeez.

      1. Some days I feel ’em, some days I don’t.

        I have seen plenty of assholes like this, and very few grow out of it. They just keep doing it, and employing new tactics until one day they screw up by messing around with a vigilant parent who presses charges, getting with a girl who lied about her age, starts luring girls with drugs/alcohol, etc. If they aren’t caught, they just get more emboldened.
        The delusions some females have when it comes to their first “love” (lust is more like it), their first sexual encounters, etc; and the way Hollywood has glamourized these things is so idiotic. Bad Hollywood, bad. *shakes her finger sternly*

    2. yes, this is the answer. please read this long and hard LW, and realize what ACTUALLY happened when you were young, not what you remember.

  7. LW, I had a similar teenage-love situation. When I was 15 I met the older brother of one of my friends. I fell into complete puppy-love with him. I thought he was the coolest guy ever and I crushed on him for 3 years until I was 18. I would stay up all night thinking about him, always had butterflies, etc…I truely thought that he was the one. And because we had been friends for 3 years before that, a lot of our friends and families felt the same way. Unlike Jack, my guy had the ability to wait until after my 18th birthday to take our relationship to the physical level. We continued that relationship for the next couple of months but I went away to college and he had been attending a college across the country. We always maintained contact but we saw each other through a slew of romantic relationship and remain great friends to this day. The thing is, I have changed during the 6 years from when I was 18. He’s not even the kind of guy I would be attracted to anymore, which is great because it keeps our friendship honest. While our sexual explorations were extremely erotic because of their long-anticipated and forbidden nature, they wouldn’t be the same nowadays. I think you are building up your teenage affair in your head and you need to find someone that you are extremely attracted to and compatible with (who is not Chris). Best of luck on this journey.

  8. I disagree with the other commentors about Chris. Here’s what she says about him:

    “While I love him deeply, I’m not sure he’s the “one.” Despite my reservations, based largely on my relatively young age and the fact that there exist certain incompatibilities that are becoming increasingly apparent, I have no desire to leave my relationship in the immediate future.”

    She doesn’t say she’s not attracted to him, or that he’s just comfortable and safe. “I’m not sure he’s the one” is wildly different from “I’m sure he’s not the one.” There’s no indication that Chis is shopping for rings, or that his feelings for her are massively greater than his for her. We have no idea what the “certain icompatibilities” are; they could be dealbreakers or fluffy balls of nothing. It seems perfectly fine to me for her to stay with him while she sorts out her feelings.

    1. Exactly. It makes me think that this “incompatibilities” are nothing more than her imagination while she dreams of what-ifs about Jack.

    2. ReginaRey says:

      While I agree that she could stay until she sorts out her feelings, I know that those feelings usually never become totally clear. I wasn’t certain that my boyfriend wasn’t the one when I broke up with him…I was really confused, in fact! But I think that’s just it – uncertainty, and for a consistent period of time, IS a sign that the relationship isn’t right. At some point, you really SHOULD be “sure.” And if you continue to be unsure…that’s a sign in and of itself.

      1. Eh. She’s 22/23, not every relationship has to be the express train to marriageville. If she likes him and enjoys hsi company, and she’s not leading him on I don’t see the problem.

        I also don’t see any problem with her dumping Chris if she’s not feeling it; I’m only objecting to the idea that she *should* let him go.

      2. lets_be_honest says:

        Would be nice/right thing to do for her to tell him how she felt though.

      3. That’s the girl version of a guy staying with a girl for the sex even though he has lost interest in the relationship. If she’s questioning her relationship enough to consider leaving him for a fantasy I would say it’s beyond fixing and she should end it.

      4. There’s not any indication in the letter that she’s considering leaving her boyfriend for Jack.

        Rather, she says “I have no desire to leave my relationship in the immediate future” and “I don’t want to jeopardize my relationship with Chris”.

      5. Landygirl says:

        Regina is 23 as well and she seems to have her head together.

      6. 6napkinburger says:

        But staying in relationship because you enjoy your partner’s company and are attracted to them doesn’t mean you don’t have your head together. And at 22/23 you can afford to. I would have loved to stay with my BF longer, even though I know I can’t marry him, but at 27, I didn’t have that kind of time. She does.

        Though I do agree with your statement; Regina does seem to have her head together. And I do agree with your implied statement that the LW doesn’t seem to, at the moment. (If she doesn’t want Jack to come visit her, this shouldn’t be a discussion and the fact that it is means she’s being wishy-washy.)

    3. I agree with you, KF. I liked Wendy’s qualification that what she’s doing with Chris is wrong IF he has made it clear that he is more serious, and definitely sees a future with her. If they’re both on the same page, then let it be. I dated guys in my early 20s that I wasn’t planning on marrying. While some people don’t understand that, I just didn’t want something THAT serious at that age. I wasn’t sure if I wanted to get married EVER, so “Mr. Right-for-me-at-this-moment-in-my-life” was definitely good enough. I had a boyfriend whose company I enjoyed, and the sex was great, and we were compatible in many ways. Eventually it fizzled. But it was good relationship “practice”, and definitely better to be having regular, monogamous sex with one person whom I trusted and felt comfortable with than bed hopping.

      Now that I’m at my ripe old age of 29 (haha), I have slightly different views. Mainly, I’d rather be single than deal with someone who’s not TOTALLY worth my time, and then some. But I see where the LW is coming from.

      1. THAT said, I think that her ambivalence toward her current boyfriend COMBINED with her misplaced longing for her first sex partner (whom I agree is just ICKY) is an indication that she should probably be single and date around. Be SINGLE…. Get comfortable with it and ENJOY IT. It is one of the greatest things you can ever learn to do.

      2. 6napkinburger says:

        me and you, same page.

        PS this is the time of night where I have a lull… I can’t leave work because I’m going to get an assignment at 8:30 that will take me til 12 to finish and I’ll need to be at my office, but I don’t have much to do. Maybe I’ll go to the gym.

  9. artsygirl says:

    LW – I feel like I need a shower after reading this letter. Jack is a class A creeper. Seriously he took advantage of you and used your emotional hormone crazed years to get a little nookie. Take a trip to your local mall and hang out around Holister or Abercrombie and Fitch and think I am the age Jack was when he was fooling around with me – do I find any of these children attractive? The answer should be a resounding NO. Teenagers are not meant to be appealing to adults. Now this is not someone I would even want to meet walking on the street let alone someone I communicate with regularly.

    Also as you said he has not had a relationship since college (before you two hooked up) – but do you have proof of that? He just said that but he has probably been sleeping around or hooking up with people in the last decade. Let’s say you disregard all the advice you are getting and decide to hook up with Jack again. Let’s say you have wild monkey sex that completely lives up to all the fantasies you have had over the last decade. Then what? He lives on the other side of the country. Are you going to move to him even though he has expressed his allergic reaction to relationships? Yeah that is what I thought….nothing good will come from sleeping with Jack. NOTHING.

    It sounds like you don’t want to break up with Chris unless you have a ‘sure thing’ with someone new. Do him a favor and break up with him rather than stringing him along as Wendy said.

    1. lets_be_honest says:

      Thank you for correctly referring them to CHILDREN. As I said above, how the hell does she not realize how disgusting that is now that shes older?

    2. Interesting theory on trolling the mall. Except for this: Many abuse victims (and let’s be honest, even if she was willing, she technically IS an abuse victim, even if the law barely qualifies her for such a labeling) imprint the patterns of abuse and will REPEAT the patterns of abuse. Ex: a boy who is molested at the age of 6 until 14 when he “ages out” of the original offender’s preference zone may grow up to like boys between the ages of 6-14 himself and have the urge to be with little boys on occasion. Could be completely heterosexual otherwise, except for that “abnormality” in thinking.
      Women who have been sexually abused as children end up with more “classic” signs such as sexual promuscuity (known as “Daddy issues”), mainly because they equate sexuality and sexual gratification for love or self-worth.
      Quite a few end up with drug/alcohol problems because they try to erase their memories, or in some cases, drug their “perverse” impulses away. Unfortunately, drugs actually heighten the bad memories and can lower inhibitions which cause a person to be more likely to act on those bad impulses (which is why an individual is more likely to sexually assault someone else while drunk than sober, or beat them, etc).
      She may very well find those kids at the mall attractive because this time – she is the self-assured adult in charge and she is teaching a new and inexperienced person. Molding that new person into a sexual being. Turning them from innocent to experienced. She has the control this time, rather than being the naif.

    3. Landygirl says:

      We should start calling you smartsygirl 🙂

  10. JennyTalia says:

    I’m going to suggest Option 3: Lose both of them, find yourself, and meet someone who satisfies all of your new-found needs.

    1. I totally agree! I feel like the LW is saying “Well, I really want to leave Chris, but only if Jack says he’s in love with me and commit to me. If not, I’ll stay with Chris because he’s OK”. I think she’s afraid to be alone. The LW needs to find someone that she’s deeply in love with but also compatible in terms of lifestyle and values. Clearly neither of these guys are it.

    2. Landygirl says:

      I’d go as far as to say that she should dump them and then figure out what she wants out of life without a partner. She’s keeping Chris because she doesn’t want to be alone so he’ll do for now. Jack is just a creep and a pedo bear.

      1. iseeshiny says:

        Thumbs up for the pedo bear ref!

    3. YES. I was thinking throughout the letter that she seems to think she has to choose between either of these guys, while the truth is neither of them will make her happy in the long run and she should strike them both loose.

  11. ReginaRey says:

    Like silver_dragon_girl mentioned, there are 2 completely different issues at play here. One is that she refuses to break up with Chris, even though she realizes that the relationship isn’t going to last. LW – I cannot stress enough how important it is to get out of a relationship when you know in your heart it isn’t going to work out. It’s unfair to Chris to keep him in a relationship that’s going to end just to keep YOU comfortable.

    The second issue is your relationship with Jack. Like Wendy said, if you know he can’t give you what you want, then don’t pursue something with him!

    What ties these two issues together is one big theme – You’re doing what’s comfortable, and settling for things that you KNOW and people who can’t really give you what you want, instead of doing the hard thing and being alone.

    Being single is hard sometimes. It’s lonely, and you miss having the comfort of a loving relationship (I get it…I recently broke up with a boyfriend I was comfortable with, but who ultimately wasn’t right for me). But you know what sucks more?? Stagnating. Staying in a relationship when you know it’s going to end. Settling for people who can’t give you what you need. All of that sucks WAY MORE than the discomfort of leaving what you know. I urge you to stop leading your current boyfriend on, stop entertaining a crush on Jack even though you know he’s not right for you, and do yourself a favor – be single for a while, and open yourself up to someone who IS right for you.

    1. Be careful…singledom is very addicting when you get used to it!

      1. Budjer, I agree. I’m in a happy 2 year relationship right now, but I had so much fun whenever I was single!

      2. 5 years single…and with each year I let myself get more set in my ways…I feel bad for my next romantic interest.

      3. Addie Pray says:

        Budjer, would you consider going on a blind date with my “friend” Regina Rey? You two could go to a bar and give everyone great, wise, helpful advice. And maybe fall in lurve.

    2. my friend and i were actually talking about the issue of staying in a relationship just because you’re comfortable this week. she’s been with her bf for 4 1/2 years and she’s starting to worry they’re both staying for the wrong reasons. another issue with her is that they haven’t had sex yet and she wants to but he’s hesitant. there are actually a lot of other issues involved, i wish she would write in to wendy because i think she needs some outside perspective (from other than her friends) to help with this. another aside with this is that they’re both 30+, in my opinion too old to be in a commited relationship for that long with no sex. i would be going crazy!

      sorry for the long rant on your comment!

      1. haha yeah…our group of friends has all thought something along this line before. but, it’s hard to get your friends to listen to you some times. which is where outside perspective would be helpful!

      2. lets_be_honest says:

        Whoa over 30 and still no sex after 4+ years. Damn!

      3. Exactly! Holy crap! In a committed relationship for 4 YEARS with no sex is insanity. She must have a great battery collection.

    3. RR- Your last paragraph. Yes, yes, yes!

      If most people understood this, there would be a lot less divorces, a lot less unhappiness and a lot more healthy relationships in the world.

      A hair stylist once told me that she has styled hair for a lot of brides. And a lot of those ladies had tears. Not tears of happiness, mind you, but tears because they know what they’re about to do isn’t what they ultimately want. They go through with it anyway.

      LW- don’t be that person. I realize marriage isn’t involved. But a lot of hurt will be if you don’t let Chris know what’s up.

    4. Jess of CityGirlsWorld.com says:

      Also, RR, sorry to hear about your break-up and hope you are moving ahead happily.

      1. ReginaRey says:

        Thanks, Jess! It’s been about 6 weeks and I’m doing well…just trying to figure out what to do with the extra TIME! haha.

      2. 6napkinburger says:

        I bought knives. Really really really good knives. I just took out a potato last night and just chopped away. Didn’t cook, didn’t make anything, other than a very very nicely chopped potato. This is what i’m doing with my time.

      3. Jess of CityGirlsWorld.com says:

        Travel? Take a class? Writing project? Paint a room in your house/apt? Book club?

        haha, these are just some of the things I’ve tried post-breakup 🙂

  12. Let go of Jack and you might find your feelings for Chris strengthening without this immature creep-tastic man littering your mind. Seriously. I think because you’ve been holding onto this teenage lust you had way back when with an older “mature” guy, you have been blinded to what you have. Chris sounds great. I wouldn’t let him go just yet. If after say a couple months after you drop Jack from you life you still find yourself feeling the same way about Chris, tell him and work from there.

  13. LW, it seems like you’re caught in a fantasy. You probably think of “Jack” as your first love. You have intense, complicated feelings for him, especially since he was your first sexual experience. And you admit he’s not the right guy for you. So what is the point? You’re obviously not going to have a relationship with him, and he doesn’t really seem like good friend material. The reason why you can’t completely get over him is because you’ve remained in touch (albeit sporadically.)
    So if you want to get him out of your head, considering you know he’s not the the guy for you — stop being in touch. It’s no hard feelings, people do it every day. There’s plenty of people we have experiences with, they don’t work out, you move on, and it’s over. I just think this guy is holding you back. Once Jack is out of the picture, your relationship with Chris should come into clearer focus.
    And to answer your question — yes, you are doing wrong by Chris if you feel ambivalent towards him, don’t see a future with him, and continue a relationship with him. My guess is he doesn’t feel the same ambivalence. And that’s not fair to him.

  14. Jess of CityGirlsWorld.com says:

    One thing about the comments on this post. Overwhelmingly unanimous.

  15. 6napkinburger says:

    I’m going to be the voice of “no reason” today.

    Break up with Chris. Or just tell him that you know you don’t want to marry him, ever. If he’s really into you, that will do it for you. It stinks and i very well understand wanting to stay with someone you know you won’t go the distance with, but you know, I know, Wendy knows, everyone knows that you shouldn’t be with him if you’re indifferent (and those “incompatibilities” will just fester and turn the whole thing sour.)

    Bone Jack. I know everyone thinks he’s a pediphile, but you don’t and you are never goingn to get over him until you pork him and he utterly falls short of your expectations. Maybe not in the actual porking, but when he doesn’t call enough or doesn’t gchat you first, or write you back, or does any of a whole bunch of the things that men do that piss off 23 year olds who are used to a comfortable, dependable relationship — you will get over him. the him in real life will never live up to the him in your head. And that’s who you have real feelings for; the him in your head. So bone the one in real life and give him the chance to suck, so you can move on.

    Wear a condom and happy dream-shattering. It’ll be worth it in the long run.

    1. This is great advice!

    2. silver_dragon_girl says:

      “…but when he doesn’t call enough or doesn’t gchat you first, or write you back, or does any of a whole bunch of the things that men do that piss off 23 year olds who are used to a comfortable, dependable relationship– you will get over him. The him in real life will never live up to him in your head.”

      SO TRUE.

      Love the comment, 6.

    3. Jess of CityGirlsWorld.com says:

      Holy crap. Impressed with your bold honesty!

    4. Painted_lady says:

      Uh-mazing, 6! I say this from personal experience that, if boning him doesn’t do it, nothing will. My high school boyfriend and I dragged on and on like a Shaun of the Dead-style zombie into my first year of grad school. I finally made the decision to jump him when he came to visit for spring break because I figured that would define things one way or the other. And it did – after, he pulled the exact same not-quite-ready-to-settle-down BS he had for eight years, just like dear old Jack has and will, but getting the reality of him was what I needed to get him out of my system for good. If we hadn’t had sex, it wouldn’t have happened so cleanly.

  16. You say, “I don’t think [Jack] could ever truly love me and treat me like I deserve.”

    Why are you so deserving of true love and accompanying treatment, but Chris is not? I understand your problem – I really do – but it is SO distasteful and nervy for you to say, in one sentence, that you “deserve” this special love and treatment, and in the next that you are basically planning to string along a good guy until you find something better. If any of you “deserves” that type of love, I think it’s Chris, not you.

    That aside, I have been in your position before and it sucks. It will be hard to let Chris go, but you gotta do it. He deserves it.

  17. Beentheredonethat says:

    I don’t think she’s necessarily toying with Chris. I think, and it’s something I’ve dealt with too, that she’s afraid Chris isn’t “the one,” because she’s comparing her feelings for him with the “all consuming” feelings she felt for Jack as a teen. She’s probably not going to feel that way again since she’s not a kid anymore, and with Jack out of the picture, I’ll bet she realizes that Chris is the one. Jack has that bad boy appeal, but Chris seems like the real deal.

  18. landygirl says:

    Now I have the song “Torn Between Two Lovers” playing in my head.

  19. Hah! Love the Bone Jack line by ‘burger. You can even generalize this to be what you say in any similar scenario when you just need to get something out of the way. Yeah, I think you’re gonna just need to ‘bone Jack’ on this one or you’re gonna waste half your life wondering.

    Though, honesly, I just want to point out that I feel like there is some deep wound-ish like thing being surfaced here. A scar being opened. When you’re 15, 16, and you have your first experience with some detached 22, 23 year old, I’m concerned that you go on, perhaps, to have that sabotage future relationships.

    For as important as first f*’s are, so are first break-ups. You have to learn how to walk on. And if you don’t, you might find your subsequent relationships all start to resemble these rock/hard place situations where you’re half- or 3/4-assing it with a guy like Chris that you can’t fully commit to because your first guy left the gate on your heart open when he left and the wild horses ran out. Go get the horses back and close the gate.

    I seen lots of people stuck between a rock and a hard place, and I han’tna ever seen it ‘cept for a body put himself there. Or herself. Why do you do that? There’s always a third way and there ain’t jail walls but those we make ourselves.

  20. I’ve said it before and I’m sure I’ll say it again:

    Dump the boyfriend. But don’t date the family friend. You need time to be single and figure out what you want out of life.

    Also the family friend sounds like a creep.

    Though I’m with 6napkinburger. Sleeping with him may not be the worst thing you could do. First loves suck to get over, but you’ve never really gotten over yours, and probably won’t move on until you do.

  21. Holy Bleep. There is a huge difference between being 18 and being in a relationship with a 26 year old and being 16. I know it sounds dumb, age ain’t nothing but a number and all that, but for most people those few years can be life changing. You just learn to drive at sixteen. If this guy really, really cared for LW he would have told her that he felt a connection but that they shouldn’t move on it until LW had graduated from high school or that they couldn’t indulge in anything sexual until they saw each other for a year or so. He would have told LW that he wanted her to really think over her feelings and that it might take time. Because, it sounds like he went 16 age of consent and went for her and that is just creepy.


  23. Painted_lady says:

    I go with dump Chris and sleep with Jack and have done. With the exception of the earliest stages of dating, if your question is “Which of two boys should I date?” the answer should always be no boys. You should date no boys at all.

    You’ve known each of these men for a long time. If you don’t very clearly want to be with one of them, you should be with neither one.

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