“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 physical in nature. He was a family friend and one of my parents was aware there was a romantic connection between us but did know its full extent. After several months of this, Jack 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. It was great to see him after all these years. However, my visit reminded me that, like with my boyfriend, there exist certain incompatibilities that I believe would hinder a lasting relationship.

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. So I told Jack that I’d try to get together at some point if he made it up to my town but would mainly leave him to his own devices. He then said he didn’t want to make the trip up just to be “alone.”

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 a cruel thing to do.

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 heartache 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, you can send me your letters at [email protected].

25 Comments

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

    2. Just a girl says:

      My thoughts exactly. This guy is a low-life

  2. 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.

  3. 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.

  4. 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. . .

  5. 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.

  6. 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.

  7. 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. 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.

  8. 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.

  9. 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.

  10. 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. 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.

  11. 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.

  12. 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.

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. 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.

  18. UM, JACK IS OBVIOUSLY A SEXUAL PREDATOR.

  19. 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.

  20. Jane who's been there says:

    You wanna be happy? Break up with Chris because he (and you too) has a right to pursue a relationship with a future. Then cut all ties with Jack who 1) was a predator when you were a child 2) is just looking forbsome fun or an ego noost from you now.
    You have no idea how powerful you will feel when you toss Jack out with the trash and get honest with Chris.

Leave a Reply

Your email address will not be published. Required fields are marked *