“I Was Engaged to a Man, But Fell In Love With a Woman”

I was with my past boyfriend/fiancé, “Craig,” for seven years. I loved him to pieces. We were best friends and so comfortable with one another. We laughed, had sex regularly, had great friends, and had similar dreams. We met in college and moved to another city to live together when we both graduated. We made great friends and established a life there. We were happy. I have always been afraid of marriage because I’ve seen so many fail, but I felt safe with him. My only complaint was his lack of emotion. He was always just stone cold; he never expressed worry or sadness to me. I’d ask him why he never cried and he just said it’s not him.

My job got really crazy — I worked almost every day and we rarely saw each other. During this time, I left him love notes almost every day to make sure he felt cherished. I left work at work and made sure to focus on him every chance I got. We still had sex regularly. We finally decided I needed to leave that job and that we wanted to get out of the city. We packed up our things and moved to another state.

Right before we moved though, a girl named Cathy, through my old job. She was gay and beautiful. I didn’t think anything of it–we were very good friends and I was happily engaged. I was not planning a wedding because we didn’t have money and marriage still scared me, but I was thrilled and felt so lucky. Cathy and I talked about my relationship all the time. She became my therapist. She knew me so well and could read my emotions and body language. I didn’t think anything of it until one night after a few too many drinks I kissed her. She tried to stop me multiple times, but I was persistent. So she gave in.

After my Craig and I started settling into our lives in our new city, I continued to talk to Cathy and soon I fell in love with her. I still loved Craig, but Cathy connected with me emotionally. She was so different than he was. We began seeing each other in secret. Craig and I continued to have a “great” relationship…good sex, laughter, motivation for life…but we didn’t have the emotional conversations I hadn’t realized I needed. I tried to talk to him about needing more emotion and feeling anxious about not knowing the inside of him, but he didn’t take me seriously. He called me silly. I wanted my mind simulated and my emotions fed. The guilt of my affair grew in my conscience. But, since I had never been with a woman, the affair was also so foreign, exhilarating, and incredible, and I told myself it didn’t feel like real cheating because she was a woman. She was just my best friend…whom I slept with (after having to learn what sex with a woman entailed) and I loved it. The guilt continued to grow and I eventually convinced myself, with her help, that I shouldn’t be engaged or be getting married if I was able to do this to him. I shouldn’t be okay with sleeping with a female behind my fiance’s back for four months. And I thought that, if he truly loved and knew me, he would have known something was wrong.

I finally sat him down one day and told him I had developed feelings for a female and I was scared. He didn’t flinch. We argued and talked for a month after this. He never shed a single tear. We ultimately decided to split, and he still didn’t show an ounce of fear of living without me. I came home one day from work to find that he had taken his things and our dog and had left. He moved to Seattle with his best friend. He didn’t even say goodbye. I decided to move to the beach once our apartment lease was up, two months later.

Cathy and I tried to date and are still trying. I love her very much, but I also feel very broken. I don’t feel ready to totally love someone else. I feel guarded and still very in love with and hurt by my ex. It’s been an entire year since he left and I still cry. I can’t seem to let go of the way he left — not saying goodbye or shedding a tear. I have put Cathy through hell with my confusion and hurt. I know I love her, but I don’t know if I want to end up with a female for the rest of my life. I miss Craig to my core. I know I felt neglected at the time and was filling the void with Cathy, but if she’s who I am supposed to end up with, then why has it been so hard for me to let go of him? Why did I have to fall in love with her? And why am I so scared of relationships now? She is willing to do anything in the world to end up with me forever, and I keep pushing her away because I don’t know what I want.

Please help. I’m going crazy and so tired of fighting with her and crying over him. — Fighting and Crying

You’re looking for someone you can have a well-rounded connection with and neither Craig not Cathy is that person. I suggest taking some time to be single. Take a year — at the very least, take six months — and just be. Just be by yourself. Learn how to be happy alone instead of looking outside yourself for happiness, fulfillment, and completion. No one is going to complete you but yourself. When you figure that out — when you learn to be comfortable and content in your own company — you’ll be ready to start dating again. If you’re attracted to women as well as men, date both. But be honest with yourself — if your only attraction to women is the emotional and intellectual connection they can offer, stick to being just friends with them. You don’t need to have all your needs met by one person. But the person you’re dating and in love with and think you might want a future with should be someone with whom you have a physical connection as well as an emotional one. You need both, and if you don’t have both, you’re not with the right person, no matter how great one particular part of your connection might be…

P.S. Therapy.
P.P.S. Stick to dating locally instead of this long-distance stuff. Distance is a great way to remain noncommittal and detached — two things it seems you already struggle with.


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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. Also, while you’re entitled to your feelings, you are overfocusing on Craig’s reactions as justification. You cheated on him, so you broke up. He doesn’t owe you tears or being afraid of living without you.

  2. Bittergaymark says:

    Eh. You shamelessly LIED to your ex all the while banging another woman for a good long while to the point of falling in love with her — and yet YOU feel hurt by HIM? Because of the way he left? Okay, snowflake. Whatever.

    1. Avatar photo Cleopatra Jones says:

      Kinda makes me think that she told him about the affair to get some type of reaction from him. She could have very well broken up with him without revealing that she had been cheating on him with her friend.

      1. Skyblossom says:

        She wanted to make him cry but instead he took the dog and left without saying goodbye. She just doesn’t approve of the reaction. The way he left speaks volumes about how he felt but she will only consider it valid if he sheds tears. Everyone has to express emotions her way or they are emotionless.

      2. Avatar photo Cleopatra Jones says:

        The dude took the dog and moved to another state. That speaks volumes about how hurt he felt.

    2. Quite right, BGM, but I would also add that this fits the classic DW pattern of “We were soulmates who were a perfect match who had this crazy connection, BUT…” You didn’t see it as a red flag that your intended did not communicate emotion in a satisfying way (for you)? I mean, you did. You said you brought it up with him. So why would you think he was a good partner for you? Then you threw your affair in his face to provoke an emotional response. If my fiancee did that to me, I might very well bug out to the west coast without a word, even if I previously could noy imagine leaving without her, because cheating is… duh! a dealbreaker for lots of people. Like almost anyone.

  3. Unwanted_Truth says:

    ” I feel guarded and still very in love with and hurt by my ex”

    What the utter fuck?!?! He may not have shed a tear in front of you but BELIEVE ,he was hurt worse by YOU and probably couldn’t bare to see you and say goodbye.

    1. Northern Star says:

      LW wants to KNOW that her ex was hurt when she ended things. I don’t know if he did or not. Maybe he thought he dodged a bullet.

  4. Yeah, I keep getting stuck on the “he wasn’t upset enough!” crap. You’re using his feelings as a validation of what you meant to him.. so you can tell yourself how wonderful you are. How about you think about what he meant to you while you were having sex with someone else? Clearly, it wasn’t what he deserved.

    Quit dating. Figure yourself out. You clearly have some growing up to do.

  5. Rangerchic says:

    I’m sure he was hurt when he found out about you cheating on him. It sounds like you weren’t a good match in the first place. Everyone shows emotions differently and he didn’t give you what you needed (which doesn’t make him bad, just not for you). Should have left him instead of cheating.

  6. Avatar photo meadowphoenix says:

    I have to say first: LISTEN TO PEOPLE WHEN THEY TRY TO STOP YOU FROM KISSING THEM. Not because you’re cheating but because CONSENT MATTERS.

    I’m not with Wendy that your fiance showing emotion wasn’t something you should, you know, be able to get from him, but I’m also not sure what you expected when he left. You told him you cheated (and yes, he did understand that “i fell in love” means you cheated, don’t think he didn’t cop that), he for real wasn’t going to be vulnerable with you then. Come on. I think you’re sad because you feel he didn’t have any deep feelings for you and frankly, you’re probably right. So now you need to accept that fact that you saw the warning that he didn’t and ignored it.

    I’m also not with Wendy that you just want women for conversation, since you said you loved sleeping with Cathy. But Wendy is absolutely right you need therapy. Honestly, that should be a priority for you. Because you don’t have to spend the rest of your life with a woman, but frankly, you didn’t seem to like being committed to a dude either. Sort your baggage before you ask someone to help carry it (or can help carry theirs).

    1. Avatar photo Dear Wendy says:

      Wait, where did I say she should have been able to get emotion from her fiance or that she was only with cathy for conversation?

      1. Avatar photo meadowphoenix says:

        if your only attraction to women is the emotional and intellectual connection they can offer I don’t know why you brought this up at all. I don’t think it applies or is hinted here enough for that to be relevant.

        And you should she should be complete in of herself, but like I feel like she should be able to get some emotional resonance of some sort from someone she’s dating.

      2. Avatar photo Dear Wendy says:

        Because she says repeatedly what a great emotional connection she has with Cathy, but she isn’t sure if she sees herself with a woman long term. I think it’s fair to advise she ask herself if she is actually sexually attracted to women or more drawn to the emotional connection.

      3. Avatar photo Dear Wendy says:

        And I also very clearly said she should have both an emotional and a physical connection from the person she’s dating.

      4. Avatar photo meadowphoenix says:

        But fair enough that I’m reading into the emotion from fiance one.

      5. Agreed with Meadowphoenix, I had a similar reaction to that part “But be honest with yourself…” The implication that she’s not actually attracted to women because she hadn’t sought out a woman before this? Not great.

      6. Avatar photo Dear Wendy says:

        No, that’s not only not what I
        Meant, it’s not what I said either.

      7. This I would agree with: “If you’re attracted to women as well as men, date both. But be honest with yourself — if your only attraction to *someone* is the emotional and intellectual connection they can offer, stick to being just friends with them.”

      8. Avatar photo meadowphoenix says:

        Because she says repeatedly what a great emotional connection she has with Cathy, but she isn’t sure if she sees herself with a woman long term. I think it’s fair to advise she ask herself if she is actually sexually attracted to women or more drawn to the emotional connection.

        No it fucking isn’t fair. “She likes having sex with women, but she doesn’t want a relationship with them” is a conclusion you can make (and is actually not even surprising, compulsory heterosexuality is something that often complicates this for people). “She doesn’t actually like having sex women” even though she explicitly says she liked (no LOVED) sex with Cathy and presumptively kissed Cathy despite Cathy’s own first refusals is not. There are very few women who decide that when they are ALREADY getting their emotional needs satisfied by someone that they need to fuck them too, man or woman.

      9. Avatar photo Dear Wendy says:

        “She was just my best friend…whom I slept with (after having to learn what sex with a woman entailed) and I loved it.” I didn’t initially interpret that as she necessarily loved having sex with Cathy. I read the “it” in the sentence as referring to the intimacy of being physical with a best friend — one with whom she shares an intense emotional bond. But on further reflection, I think you might be right.

      10. Bittergaymark says:

        Eh. I dunno. I don’t see that anywhere in the letter. Hell, the LW seemed dumb as fuck about lesbian sex. “After learning what it all entailed…” Really? Really, REALLY? What? She’s never thought about it? Fantasized about it? WhatEVER. I damn well knew all about man on man sex and what entailed YEARS before I even kissed that a guy. The LW seems almost as into women as I am. No. Wait. Actually, I’ve slept with three of them.

      11. Anonymous says:

        I’m glad you figured it out Mark, but if a distressing number of hetero men don’t seem to know what to do with a woman’s body, and a distressing number of women barely know how to please themselves, I can’t fault this chick.

    2. dinoceros says:

      Yeah, I saw this more as any other emotional affair (that turns into physical). I’d assume she’d be in a similar position with a man who filled this role for her. If her issue was that she was over Craig but not attracted to Cathy anymore, I’d be more concerned about her interest in women, but at this point, I don’t think she’d be happy with any gender until she gets over him.

      1. I agree for the most part, especially that she won’t be happy with anyone until she figures this out (and has time as single, like Wendy suggested).

        Though I don’t know if I’d go questioning someone’s sexuality even if things fizzled with both. We wouldn’t advise someone who had emotional affair that turned physical that maybe they’re actually asexual and were really only in it for the emotional connection with the affair partner, right?

      2. dinoceros says:

        I didn’t mean that we should question her sexuality if her relationship ended with both. I specifically was referring to if she suddenly stopped being sexually attracted to Cathy. I don’t think we should be questioning anyone’s sexuality, but I was responding to others who had. My purpose was in saying “I could see how some situations might make you wonder, but this one is far from it.” But yes, even if she immediately stopped being sexually attracted to Cathy when her relationship ended, we shouldn’t question it.

  7. After the way you treated Craig, he owed you nothing. Not a goodbye, or anything else.

    You lied to him, cheated on him, and then were upset with him because…what? He didn’t grovel at your feet and beg you to stay with him? He didn’t make a big showy display of grief so you could get off on knowing how much you’d hurt him?

    The sheer self-absorption in this letter is appalling. Craig and Cathy weren’t put on this earth to fill your needs and make you feel special and important.

    Stop dating, until you’ve spent some time with a therapist and learned how to treat people.

  8. Northern Star says:

    Good for Craig. Seriously. I’m glad he did what had to be done, which was remove you from his life and hopefully move on to a new woman who won’t have an affair with someone else behind his back.

    I’m surprised Cathy wants to be with you, because you’ve shown her just how trustworthy you are—but I doubt it will last because you sound self-centered as all hell. Do you care how she probably feels, knowing you are still mooning over your ex-fiance and nursing hurt feelings because he didn’t grovel to get you back?

  9. The part that bothers me is the line, “Cathy and I talked about my relationship all the time. She became my therapist.” I am a lesbian and I know that that’s a HUGE red flag. It suggests codependence and a one-sided relationship. Of course you are having trouble dating her. Your relationship has a very unhealthy beginning. If you DO decide to date women, be careful.

  10. Oh poor, pitiful little LW. She cheats on her fiancé and lies to him for months, but he is an awful cad who didn’t give her the personal, abundantly tearful, good bye, which she needed to validate her self worth. That’s not his job. You became his ex through your own actions. He gets to move on however works best for him. He doesn’t owe you sobbing validation of how much he loved you, what an awesome woman you are, how he doesn’t know how he can face the road ahead. If he was too unemotional for you or your conversation wasn’t stimulating enough, then you had a clear choice: you could call off the engagement and move out. Deciding to cheat is not acceptable. Discussing the ins-and-outs of your relationship with Craig and his personality, and what you see as his defects, and how difficult you are finding life with him with your new gf is a gross betrayal of trust. I only have your side of what happened and I still can’t avoid thinking you are awfully selfish and slimy.

    1. Right. Scratch my comment above and go with this better version of the same point.

  11. “…if he truly loved and knew me, he would have known something was wrong.” Lots of “wow!” going on over here, but way to heap the blame onto Craig here!

  12. dinoceros says:

    As I see it, the main issue here is that you cheated on Craig not because you weren’t in love with him anymore, but because you loved him and he wasn’t giving you what you needed. That’s why it’s so painful to have lost him. I don’t think it necessarily reflects on your feelings for Cathy (maybe she’s someone you could have been happy with), but the way you went about this means that you’re trying to pursue a new relationship with someone while you’re still not over your ex, and that doesn’t turn out well.

    To me, this is a thinking problem. Navigating relationships is hard, but one important piece of that is being able to look beyond the immediate and think about long-term effects. If you date someone who shows no emotion, you need to think deeply enough to realize they may not be a good partner. If you date someone you aren’t compatible with for a long time, you have to think deeply enough that it’ll eventually end and you’ll be sadder the longer it lasted. If you cheat on your partner who you still love, you have to realize that they might dump you AND you’re not going to be ready for a new relationship. You never thought about this stuff. You’ve GOT to use your brain sometimes, and not just your emotions.

    Finally, I think you need to see a therapist. A year later, this isn’t about Craig. This is about a lot more deeper emotions that you need to work through. I think you need to stop seeing Cathy and work on yourself for a bit. And I think a piece of that is realizing that Craig was not out of line for breaking up with you the way he did. Despite his emotional issues, you cheated on him. A cheater isn’t owed a diplomatic breakup.

  13. wobster109 says:

    I’m sympathetic to LW even though I agree she handled it poorly. LW probably felt very lonely after 7 years of small talk, especially with Craig telling her that her needs were “silly”. It’s reasonable to want to connect to a partner emotionally, just like it’s reasonable to want good sex.

    But it should be handled the same way. LW, if you wanted to have better sex with your partner, first you’d talk to him about it. And if he never improved in 7 years, then you’d see a sex therapist, or talk to him about having an open relationship, or decide to live with it, or break up. You wouldn’t have sex with other people to fill that gap while still keeping it a secret from him.

    You had the same mature options here: therapy, or breaking up, or discussing other options with Craig. Not sneaking around. In the future please choose one of these options, even if a discussion is more difficult in the short term. It’s more work up front, but it saves you the anger later on, and it keeps your integrity high.

    And don’t date Cathy. Too much back history. Time to make a fresh start.

  14. I think really at your core….you think love should personally cost you a great deal to be worth it. You don’t enjoy the everyday aspects of expressing love-the being there, quietly sharing company. You need constant tension-uncertainty if you will. graduating, moving, stressful job, moving again, those are the milestones you chose to share with us from your time with Craig. As soon as things settled down in other aspects of your life,where the engagement could turn to something more, you CREATED this drama because I think, you couldn’t bear the thought of settling down. Only you know if your feelings for Cathy are true, if you are truly sexually attracted to women. And now that things with Cathy have settled down, you go back to your ex, dredging up old feelings, again, because you are at a point of CHOOSING. Let me say nothing your ex Craig could tell you will begin to fill the void you feel within yourself. No matter if he told you he still loved you, whether he said he too, didn’t love you anymore but was just going through the motions, whether he regrets how he left-it won’t help. I think your self involvement is so much at this point that no explanation would ever be good enough. I agree whole heartedly with Wendy you should take a step back and work on yourself.

    1. This is a really good comment.

  15. I can’t work up sympathy for LW. She is very emotionally selfish and couldn’t bring herself to commit with either Craig or Cathy, but she’s the victim who needed more substantive conversation and emotional openness.. She says that she couldn’t have deep conversations with Craig. Yet, it doesn’t appear that she has deep conversations. She just likes to talk about herself, ad nauseum, which is what se did with Cathy. Tough for Cathy when your gf just wants to talk about herself and her relationship with her fiancé and not getting the emotional connection she requires. Given the grievance she wrote in about: Craig left without a tearful goodbye. He failed to cry when she revealed her cheating. It really just does sound like she needs to be told over and over how wonderful she is, how emotionally tortured she is, how unappreciated she has been. She cheated and he left without a goodbye, but she’s been flying the victim flag for a year, while holding her girlfriend, whom she also supposedly loves, at emotional arms length. Frankly, LW is the one who seems emotionally crippled. Craig’s since was not spinning her a long tale about how he was equally tortured and crying periodically. Actually, character is revealed by how we act in good or bad times. That’s not LW. She’s a cheater and she craves a soap opera. She is one of those who equates drama with passion and a great love. One wonders exactly what Cathy’s sin is.

  16. Morecoffeeplease says:

    LW, make an appointment with a therapist. You have a lot of work/learning to do about yourself and relationships. You must realize that Craig would never have given you the emotional support you need, so if you had stayed with him you would have just grown unhappier each year. He was not the right person for you. Second, I’m not sure you really understand that you can’t cheat on your partner and use an excuse like they weren’t giving you emotional support. What you did was beyond the pale. You cheated on him..not just a one time fling either but an emotionally connected falling in love kind of cheating. That was cruel of you to do to him. You should try being single for a year or so and do therapy. Next time you are in a serious relationship and you are not getting all you need you should focus on working on your relationship. If it doesn’t work out then break up with someone BEFORE starting a new relationship. PS – Craig did nothing wrong by leaving. You treated him like total crap. Stop focusing on that…it shows how self centered you are.

  17. This letter is in today’s Wayne and Tamara column.

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