“Should I Tell My High School Boyfriend I Have Feelings For Him, 20 Years Later?

I dated a guy, “Joe,” in my senior year of high school while I was also involved in a long-distance relationship with a guy, “Tim,” whom I met on vacation the summer before. Tim agreed we would be dating other people, but we kept in touch because we liked each other. Anyway, Joe asked me out and we started dating in August, but then he abruptly broke up with me on Christmas Eve, right when we were exchanging gifts. He didn’t date anyone after me for the rest of the year, and we basically avoided each other.

I was heartbroken and confused, but, after the breakup with Joe, I decided to throw myself into my long-distance relationship with Tim. We started talking more and more and made arrangements to see each other about monthly. He took me to prom and we were serious from then through college (always long-distance), and we eventually got married and had three kids. We’ve now been married 20 years.

My ex-boyfriend from high school, Joe, happened to go to college near me. I only saw him once at a party three years after our breakup, but we talked and he came to my apartment and stayed awhile, just holding me. He had a long distance girlfriend then too. It was like we both wanted to make a move but were scared to and would have felt bad if we did because of our respective significant others. Suddenly, he left after an hour or so and that was it. I never saw him again.

Years later, he saw my mom’s name on a conference list and sought her out to see how I was. He was married by then, but he got my email and he emailed me. I don’t really remember his email, but he said I replied once and, after that, his messages came back undeliverable. Maybe I blocked him, I can’t remember. Fifteen years after that, he messaged me on Facebook. He’s now been married 18 years. He just seemed to want to catch up. I didn’t reply. He messaged me again two months later. I was going to a reunion and feeling nostalgic, so I replied. (He is a year behind me, so he wouldn’t be at the reunion).

Anyway, we started talking, and he told me he always thinks of me when my favorite band comes on the radio. We did some reminiscing every few days for a week or so. Then we talked on phone because I had to tell him about my husband’s brain cancer. He complimented me for being so strong. We texted some more every week or so. He then said he wanted to apologize for being a jerk to me in high school. He wanted to explain in person, he said. I was curious and had business his way, so we met for lunch. He said he was having a lot of family issues back then. We had a deep conversation and caught up. He’s still married, with two teens. He has done well for himself and looks to be a great dad and husband, and he has his own business on top of his job. I have always felt drawn to him, but we never had sex as we were only 16 when we dated.

My marriage was a mess before my husband’s cancer and the tumor makes my husband act obnoxiously (his personality changes). He is on disability and won’t do housework even thought he is stable now and can do things he wants to do. I am sympathetic and have been his biggest supporter through 2.5 years of his brain cancer treatment, including three surgeries and several weeks in the hospital. I feel loyal to taking care of him and our kids, but I have almost packed up several times.

Now, all I can think about is Joe. He occasionally messages me late when he is coming home from his second job, and we chat. We have had lunch twice and he said I look great. He always says he hopes to see me again or talk again, but sometimes we aren’t in touch for a week or two. When he does call, he always asks how I’m doing and I’ve told him it’s not easy with my husband. He likes all my Facebook stuff almost immediately…

I want to just come clean and tell him I’ve always liked him. Should I or not? It’s killing me because I can’t talk to anyone about this. He said he told his wife we had lunch. I haven’t told my husband about him because I would never hear the end of it even though it’s just platonic now. I don’t intend to start a physical thing but want my feelings for him out in the open. I want to know if he feels the same way after all these years. He did seek me out several times, after all; was it just to reconnect as friends, or does he want more? — Going Nuts

First of all, I’m very sorry about your husband’s illness and the toll it has taken on him, you, your relationship, and your family. I can only imagine the kind of stress you’ve been under the last few years, especially if, as you say, your marriage was “a mess” even before his diagnosis. And now you probably feel like you can’t leave him because he’s sick, and, while your loyalty is admirable, the truth is that starting an emotional affair with someone else — a married man, at that — isn’t any better than leaving your sick husband. It’s worse. It opens a can of worms I don’t think you OR Joe, your former high school flame, are prepared to deal with. Please, I urge you — close this can, leave the past in the past, and deal with your marriage without the distraction of someone else who is very likely as lost as you are.

There’s a reason Joe has sought you out throughout the years, and my suspicion is that it has as much to do with disappointments in his own relationship and life as any nostalgic feelings he might have for you personally. Maybe his marriage is a mess, too. Maybe he’s lonely. Maybe he’s looking for something to connect him to the young man he used to be when his future was a blank slate and before the reality of life’s responsibilities started knocking him around. Maybe the period you were together in high school was a pivotal moment in his timeline when the course of his life swerved and he thinks that, by connecting to you, he can somehow go back and get a re-do. Maybe you just are a friendly voice amid the noise of his current reality — a distraction, something or someone that demands nothing from him.

I imagine he is some of those things for you, too. I can appreciate how the temptation to lose yourself in the fantasy of what could have been or what might be between you is awesome. Amid the noise of your messed-up marriage and your husband’s cancer and the demands on you to keep it all together and support your family is this friendly voice who listens to you and compliments you and tells you you look great. But it would be a mistake to give this friendly voice from your past anything more from you. It would be a mistake to hear in his voice an offering of anything more than what it is: an equally lonely cry for an escape from the shackles of everyday problems.

You can’t be that escape for each other. Not now. If you were both single? Sure — go for it. But you’re not. You both have spouses. You both have families who need your attention. Deal with the mess you say your marriage is. Go to counseling. Get support for family members of cancer patients. Consider your options. Don’t stay in a marriage that no longer works for you out of some sense of obligation. Don’t look elsewhere for the freedom you crave, because doing so will only create more burdens and problems. Don’t look toward the past for answers or escape; look ahead. You can be your own friendly voice of support. You can be your own hope of freedom. It’s not too late to have the life you want. But a boy you knew when you were young who has grown into a man with a marriage and problems of his own isn’t how you’ll get it. He may be a nice distraction in the short run, but he’ll create far more burdens and heartache for you in the long run.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. WWS, LW.

    I cannot even imagine how difficult it must be, to be dealing with your husband’s cancer diagnosis and treatment, in a marriage that was, as you say, “a mess” even without the cancer. It is so easy to see how tempting this rekindling with Joe must be. He’s a reminder of a time when your life was so much less complicated than it is now. And he’s nice to you, and he tells you how good you look, and you don’t have to worry about who’s cleaning house or making sure the kids did their homework or any of the other responsibilities you have at home that your husband no longer helps with. I’m sure these messages and phone calls and lunches are a wonderful escape for you. But your life is never going to get better than it is now if all you do is escape. You need to start dealing with the very real issues in your own life, rather than the imaginary potential Joe represents.

    I think it’s normal to be a tad nostalgic about exes from time to time, in a “how would my life be now if that had worked out all those years ago” sort of way. But letting that interfere with your actual, real life isn’t healthy for you. And you and Joe dated when you were 16. You have no idea how compatible you’d be on finances and long term plans and those little quirks like his complete inability to not leave the sponge in the sink or the towels on the floor. Also, you’re both married. And even if you do decide to leave your marriage, don’t let it be on his account. Let it be for you.

  2. LW, PLEASE listen to Wendy’s advice. If you keep this up it will NOT end well.
    One of my best friends is going through something similar right now in the fact that her husband is essentially having an emotional affair with a girl he met on his gaming site. She lives in a different country so they (hopefully) won’t ever meet, but he’s been talking with her constantly. When my friend gets home she says he’s so chipper and happy and lovey towards her, but she knows it’s because of this other woman and not my friend, his WIFE. They have lots of other issues and honestly this is just the icing on the cake, but she is literally heartbroken and she is seriously considering leaving him.
    I’m sure it hasn’t been an easy road for you with your husband’s diagnosis, but this is truly when he needs you most. Please be there for him and don’t add drama by maintaining contact with your high school boyfriend. It won’t end well. Look ahead to the future.

  3. NO NO NO NO NO.

    LW, stop it. Just stop it. You are romanticizing this beyond belief. Do not tell this guy you like him. Do not talk to him anymore. This “thing” that you have going on would not survive real life. What do you think is going to happen? You tell him you like him and you two ride off into the sunset and live happily ever after? NO. Just stop it. Stop talking to him. Stop meeting him for lunch, stop texting. Just MOA.

    1. “What do you think is going to happen?” — this, exactly. i mean what is the end game here, LW? you are treating this rekindling like some people treat drugs and alcohol- you use it when it suits you to escape from whatever shitty thing is happening (and im not judging- ive done it, and i can totally see why you need to do that!). what do you seriously think, and/or want, to happen after you tell him you still have feelings for him?

  4. Avatar photo LlamaPajamas says:

    I watched a movie about basically this same situation (minus the brain cancer) last night – it’s called See Girl Run. It’s so easy to romanticize an old relationship when your current one is in trouble, but it’s not going to end well. That doesn’t mean you have to stay with your husband, just don’t idealize this old boyfriend who may be good to you but clearly isn’t that great to his wife.

    1. I’ve seen that movie – incredibly real and sad! LW, it’s worth a watch if you have the time.

      And I love Robin Tunney, ever since Empire Records.

      1. Avatar photo LlamaPajamas says:

        I love her, too! She’s actually the reason I watched it. The movie ended exactly like I hoped it would, even though it was still devastating.

      2. Agreed! At first, you kind of want the old flame to rekindle, but I think the ending is much more satisfying and realistic.

  5. lets_be_honest says:

    One word, LW: YOLO

    1. lets_be_honest says:

      Oops, read the letter now.
      LW, sounds like you have a ton on your plate and this fantasy you’ve built in your head sounds a lot nicer and easier than real life. I get it. But in reality, its just a fantasy that if you try and make it a reality, it won’t end well for the two families involved.

  6. Answer before reading the letter: no.
    Answer after reading: WWS, don’t ruin lives over what could have been and address your own marriage first. “I don’t intend to start a physical thing but want my feelings for him out in the open.” Sounds like you want validation, but it’s not worth doing more damage to everyone involved just for that.

  7. Avatar photo theattack says:

    LW, Think about what you’re considering here. You are considering leaving your husband for a man who you briefly dated before you even knew who you were. Think about how different you are now from when you were 16. He is just as different too. Reminiscing over old memories is not a foundation for a current relationship. You don’t have a foundation for anything with him. He is not worth the amount of trouble you would be going through.
    As for your marriage and your personal life – go to therapy. You are in a very tough situation at home, trying to reconcile the difference between being a supportive wife and being a happy woman. That’s a very difficult balance that many women deal with, but your situation sounds especially complex. Talk this out with a therapist for a few months before you make any decisions.

  8. Avatar photo lemongrass says:

    You say that you don’t want to start a physical relationship but what do you expect to happen after you tell him your feelings? That is something that you can’t turn back from. If you want out of your marriage this is not the way to do it. You can step out without blowing the whole building up- with both your families inside. If you do truly care for him, the nice thing to do would be to let him go.

  9. God, Wendy, you just nailed it here. I think many times we respond to these kind of plights with admonishments and ethical reminders. What you did was to debunk the fantasy which I think is so much more helpful and effective.

    1. Avatar photo lemongrass says:

      Mike is Tim, it’s just a missed fake-name change.

    2. lets_be_honest says:

      You don’t know Mike?!

    3. Avatar photo Dear Wendy says:

      Oops, should be fixed now.

  10. Well said Wendy!
    Good Luck LW.

  11. quixoticbeatnik says:

    Thank you, LW, for giving me a glimpse of my potential future. I appreciate it, since I don’t want to end up like you.

    Now, you should cut off all contact with him. You are flirting with danger here – and that’s what HE IS. He’s dangerous to your marriage. I suspect you like using him as a means of escape. You like the thrill. He’s another man who isn’t your husband, and you have a history. I speak from personal experience when I say that I think you just want him to want you, because of how he ended things in the past.

    Let go. Focus on your husband and your marriage. Go to therapy or counseling. Find some help that can take over some of your burden so that you aren’t doing everything alone. Carve out a little bit of ‘me’ time where you can focus on yourself. Don’t lose yourself, because that’s where the real problems start. You can do it. Don’t let a fantasy ruin your life. If you’re truly unhappy with your husband, then focus on THAT instead of trying to escape with a former fling who is also married.

  12. findingtheearth says:

    I dated someone who suffered at traumatic brain injury while we were dating. I can’t say it is like brain cancer, but the behavior change and such was horrible. I stuck it out for almost a year, and had to leave because he became physically abusive.

    Get a support group. Talk to his family and your family about the reality of the situation. Have his doctors get involved. But make sure to take care of yourself, and having an emotional affair with someone who you have barely spoken with outside of online interactions is not taking care of yourself.

    Be fair to your husband, even as hard as it is.

  13. Avatar photo Addie Pray says:

    Aw, that was really great advice from Wendy. LW, read and re-read what Wendy said. Also, I think only bad things can come from Joe. He keeps abandoning you and in a really shitty way: from abruptly breaking up with you in high school on xmas eve without any explanation, to suddenly leaving after an hour of whatever-it-is-you-were-doing-in-college, and then just the one email and then nothing (ok I guess he says he tried to send more but they came back un-deliverable). I guess my point is, he doesn’t seem like the kind of person who is going to be there for you. And considering all you’re going through, you’re probably needing someone or some group or something that can give you the support you need to…. wait, what do you want? I was going somewhere with this but then it dawned on me that I’m not really sure WHAT you’re looking for. I guess I assume is is something to help you cope with your husband’s illness and to help get your relationship with your husband back on track.

  14. Bittergaymark says:

    Ugh. “My husband is battling brain fucking cancer — and now he won’t do any housework! Am I really a hopelessly deluded and utterly unsympathetic horrible person?”


    1. Maybe I’m just in a bitch mood today, but I’m glad BGM said it. Look I appreciate that it’s hard with a spouse who is sick, but seriously considering telling another married man you have feelings for him and justifying it with (1) your marriage was a mess before your husband got cancer (newsflash: it didn’t get there just because of him) and (2) your husband’s cancer makes him act like an asshole is just … well, asshole behavior. Sorry. By my count, there are at least 9 people who are potentially involved here – at least 5 of whom are the LW and Joe’s respective children (or “children”, they may all be teens/young adults, but still), 3 of whom are dealing with their father having a brain tumor that drastically alters his behavior, and 1 who actually has a brain tumor, and all the LW can think about is herself and her fantasy life with Joe, a winner if I ever saw one. JFC, LW. Get to therapy. Find a support group. Seek out the emotional support and help you understandably need and deserve to have. But, whatever you do, don’t fuck up 9 lives because you’ve convinced yourself that you’re in a rom com where Prince Joe is going to sweep you off your feet and save you from your mess of a marriage and sick husband.

      1. WMMJS x a million

      2. BGM + Miss MJ– best responses I’ve seen/read today!

      3. Avatar photo Addie Pray says:

        oh man, what Miss MJ said.

      4. In the movie version, she tells him that she has feelings for him. He cuts off contact because it’s bad for his marriage (he’s a good guy, remember?). The sick, mean husband dies. Months pass, and while cleaning out some things she finds a letter written from the husband before his cancer affected his moods and urges her to love again because life is too short. Kids notice man that liked all of mom’s Facebook posts and Facebook stalks him to find out he’s divorced now because his wife had an affair with her boss. Kids create fake profiles and trick mom and Joe to meeting up at a cafe. He brings flowers. They live happily ever after, and Nicholas Sparks gets richer.

      5. Avatar photo iwannatalktosampson says:


      6. Avatar photo Addie Pray says:

        I love you.

      7. Yayyy! Best Cinco de Mayo ever!

    2. tbrucemom says:

      Thanks, you read my mind. He’s got brain cancer so I’m sure his life expectancy isn’t very long. They’ve got kids that have a father WITH BRAIN CANCER. Don’t kid yourself that you don’t want anything to happen. Ruining 2 marriages and the lives of so many children because of selfishness. What about til death do us part? Look, I get that it’s not easy but don’t ruin the lives of so many because of some school girl fantasy. I also have to ask is the LW still in high school because some of her comments sure sound like she is. “He likes all my Facebook stuff almost immediately”, well of course he must like me.

      1. Simonthegrey says:

        The FB thing really did it for me, too. The hell? Gee, some guy I was friends with and went on a date with in high school still likes my facebook updates. Guess we’d better both break up our marriages because we were meant to be together.

  15. In my world what she already is doing is cheating…..just saying. Lunch, texts, facebook, phone calls, etc…..

  16. This sounds like typical crush la-la-land stuff (and I don’t mean this in a mean way, I’ve been there). You’re feeling attracted to Joe, so you conclude that you must tell him and that somehow this will be helpful and that it won’t lead to a physical relationship. The thing is though, if you confess your feelings and he reciprocates there’s a huge chance you’ll physically cheat on your husband. You’re deluding yourself if you don’t believe you’ll go there. There are endless problems that having an affair with Joe would create. Among other things he is married, too. It’s just not worth it.
    I definitely believe you’re feeling trapped and unhappy in your current life and looking for an escape. You need to address these issues directly, as difficult as it may be. Find out what you can do with regard to the relationship with your husband. Can it be improved? Is it essentially over? Would divorcing him be feasible? If it isn’t can you at least seek affection outside your relationship in a more ethical way (i.e. not with someone who’s married as well)? Pretty much anything would be better than going for Joe!

  17. TheGirlinME says:

    ok, The whole “high-school b/f daydreams aside” and since what-if’s are allowed – What if the difficult marriage became that way due to Husband’s erractic (possibly verbally/physically abusive) behaviour PRIOR to being diagnosed with the brain tumor? I agree with the advice that some other person is NOT the answer to problems at home.. But are we now saying that there IS an excuse for those behaviours? – How long does “sickness and health” hold sway? Sure – it sounds terrible – The poor man has BRAIN CANCER!! How could anyone THINK of asking such a question?? I don’t know..

  18. Northern_Coast says:

    What a terrible, difficult situation. Many commenters here are quick to judge the LW. I don’t know if any of you have lived with a seriously ill family member… I haven’t, thankfully. But I’ve seen it with others, for instance with my boyfriend’s mom when her husband had cancer. Your day-to-day life is just so depressing that you cling to anything that promises a way out. In her case, it was new-agey healing attempts, and the LW’s way is daydreaming about her highschool boyfriend.
    I know it’s shitty to leave your sick husband, and I’m not advising the LW to do it. But saying it’s completely unrealistic that a relationship with the ex-boyfriend could work out isn’t necessarily true either. I know two people (friends of my mom) who used to be a couple when they were 13/14, and when they were in their 40s, they reconnected, left their respective families and got married to each other. It’s weird and probably a rare case, but it CAN happen.

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