Updates: “Engaged in a Gender Bender”

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today, we hear from “Engaged in a Gender Bender” whose fiancé confessed to her that he was “really considering a sex change.” “She wrote “I don’t want to lose my fiancé, and I’m afraid to tell him that it wouldn’t work with us on a romantic level after he changed because I know it’d break his heart. Should I even try to be with him in that way after?” Keep reading to see what has happened in the three years since the LW wrote in.

First of all, I want to thank you, Wendy, and anyone else who left a comment on this letter. It has been almost three years since that column, and my life has changed forever. Spoiler alert: my fiancé and I are no longer together. But let me explain what happened. Believe me, the blindsides didn’t stop with my fiancé’s confessions about his sex change. It might be easier to write this in sort of a timeline form.

Fall 2011
I submitted my letter and read the first few comments of the column. During this time, I barely spoke to anyone. My world sort of shut down. I was the only person besides my ex-fiancé’s mother whom he had told about this, and he wanted to keep it that way for the time being. I decided that I loved him so much that I was willing to put aside my sexual preferences (I’m a very hetero woman) to try and keep this relationship alive. Having just lost my virginity, which again I should have clarified in the comments, was something very very special to me. I know that might sound silly, but for 21 years I knew that it was something that I wanted to save for the person I would be marrying and spending the rest of my life with. It also should be noted that his news was broken to me less than 48 hours after he took my virginity. He was not a virgin, and he actually had had many sexual partners before our relationship started. I was so confused. But I kept feeling that, whatever turmoil I was experiencing, his had to have been much worse.

At the end of the year, everything changed. We were living together when his computer stopped working one day and I allowed him to use mine. Soon afterward, I turned my computer on, and my browser, which apparently had been left open when the computer was last shut down, loaded the previous session. What I saw crushed me. (I would like to point out that I had always trusted my fiancé, and I had never gone through his phone or sifted through his email. I actually made a point to look the other way when he opened his phone to send a text). My fiancé was sending sexually explicit messages to other women and was trying to start relationships with them. I confronted him about it, and he expressed that it had been going on for several weeks. I felt physically ill. Not only had the man I loved turned my world upside down with his sex change news, but he also shattered my world by betraying me with infidelity. I was done. I broke up with him and stopped speaking to him. I was so enraged by what happened. I buried that pain and held my head high and vowed to start a new life. But life doesn’t always go as we hope.

Fall 2012
I hadn’t spoken to my ex for almost a year. Then one day I was walking to meet some friends for a drink and, as fate would have it, he appeared right in front of me. Now, in the year since the break up, I had grown miles from where I had been when we broke up. I realized that feeling guilty by my reaction to his confusion wasn’t helping. When I found out he was cheating, I stopped being confused and moved on. I dated someone briefly at the end of that summer but it didn’t work out, and I split with that boyfriend only a week before running into my ex.

When I saw him that night, I was shocked. He looked exactly the same. He told me he wanted to talk to me, but I had to meet my friends. He called me the next day, we met up, and he filled me in on what had been happening. He was maybe “some day” planning to go through with the sexual reassignment surgery, but, in the meantime, he was in therapy still trying to figure everything out. He broke down in front of me and told me how hard it was that last year going through everything without me. I felt so bad for him. He truly looked remorseful. We got back together.

Things got quite serious again, and I really thought this could work. But wow, I could not have been more wrong. Things spiraled out of control very, very fast. One weekend, when he had left his computer at his friend’s house, I let him use mine to get some work completed. He used my computer on and off that whole weekend. At the end of the weekend, I went to check my email again and my world was destroyed. He was communicating with an old girlfriend, and what they were discussing wasn’t good. I also saw that it had been going on for several months. The emails totaled in the thousands, and I saw the dates reached as far back as spring of that year. They talked about running away together, how he thought of her when he was lying next to me, what their wedding rings would look like, and just all kinds of things of that nature.

I was livid. How could I let this happen to me again? I felt so stupid. I felt so betrayed. I confronted him about this and he didn’t think this was wrong. We were in an exclusive relationship and we both said “I love you,” so this was so shocking to me. He couldn’t see how his talking to this girl was a betrayal to me. He told me that, because he hadn’t seen her in person in a few year and what was going on was all over the phone and email, it didn’t count. He told me it didn’t matter. I knew that I could never be with him without wondering if he was thinking of her, and we split for good. We never dated again.

Early 2013
A while later, something strange happened. I was getting ready for a first date with a guy my friend set me up with who was a real catch. I was so excited. He arrived to pick me up, and I invited him inside while I finished getting my things together to leave. Then there was a knock on the door. I looked through the peephole and saw my ex. I was blown away. What on earth was he doing there? I apologized to my date and stepped onto the porch to ask what was going on. My ex asked if I was dating this guy, and I said that my life was no longer any of his business. He started to unravel. He started screaming at me, and I was terrified. My date stepped outside with my jacket and bag in his hand, and he asked if I was ready to go. He handed me my things, and I said to my ex that I was leaving and that he needed to leave me alone. As my date and I walked towards his car, my ex started coming after us, and then he began screaming at me as I got into my date’s car. I was so upset I couldn’t even pay attention to what he was saying when he was yelling.

My date and I sped off, and I broke down in tears. I was shaking from fear. I felt horrible for my date. He must have thought that I was crazy. But, luckily for me, he was incredibly understanding. Instead of being creeped out by the whole scene, he immediately asked if I was okay. I only told him it was an ex of mine as I didn’t really want to drag out the whole story on a first date. After that, he and I dated for a couple months, but it ultimately didn’t work out. But I’ll never forget how understanding he was after witnessing what appeared to be an un-aired episode of “Jerry Springer.” I just remember that, while my ex was screaming at me, I was so upset and scared that I could barely open my mouth to say anything back.

Fall 2014
Fast forward to now, fall 2014. I haven’t spoken to my ex since that last incident. He has tried to contact me occasionally, but after the summer following our last encounter his attempts ended. In fall 2013 I started dating an amazing guy, and we have been together since. I just recently told him what happened when I lost my virginity and what a wild ride it was after that. He was very understanding. He has been my rock, and I don’t know what I would do without him. We have been together almost a year. I started my first year of law school at a top-tier school. My life is so incredibly different from when I lost my virginity. It’s like I can finally breathe.

From what I can gather now, my ex is still a man. He is now a lot more open about his struggle with his identity and finally came out to some of his friends. We don’t share any mutual friends after the cheating. To this day, I still have not told anyone about his secret. Not that it’s so secret anymore, but I know that it is something personal. Despite everything that has happened with him, despite all the pain he put me through, I would never dream of using that secret against him, even though he probably deserves it. He not only cheated, but he also took a lot of my stuff and never gave it back. I’ve loaned him over $1,800 dollars, and I know that I will never see that money again. But no amount of money can match the price of what I’ve learned about myself. I learned that I am resilient in ways I didn’t think I ever could be and that life is very unpredictable.

To everyone who wrote in response to the first letter, I just want to thank you again. That was one of the darkest, most turbulent times of my life. Your kind words have meant the world to me. I don’t know if anyone’s going to read this whole letter, or if it’ll get posted, but I thought that, because of the amount of responses to the original letter, you all deserved to hear the aftermath. I am so grateful for all of your advice. From the bottom of my heart, thank you.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at [email protected] with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

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  1. Avatar photo Addie Pray says:

    Wow, what a whirlwind the last few years have been for you. This was the coolest update – for us – just to be able to hear about everything over the past few years – but also for you – so much has changed and you seem to be in a really good spot. Good luck with law school and your relationship!

  2. Oh wow, LW, I am so sorry for all the crap your ex fiance put you through. I am happy to hear your life is so much better now! 🙂

  3. Wow, well that went downhill. I’m so glad you got out of such a crappy situation (pretty much the things that happened after your letter). That confrontation is absolutely frightening to hear.

  4. karenwalker says:

    Congratulations for moving onwards and upwards! That’s awesome that things are going so well for you now!

  5. That was a very happy ending. I wasn’t around for the original letter, but it is so great that you stayed strong through it all and proved to be such a resilient woman. Good Luck in law school and congrats on finding someone who treats you so much better.

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