Thus far, I have shared stories of the utter failures of my dating experiences. But every dating story has two perspectives of what happened. And because I’m a fair person (and a bit of a masochist,) I reached out to a woman I dated to get her side of things. Sara without an “h” and I met online. She had just returned to the states after two years in the Peace Corps. Based on her profile and our initial messages I was able to assess that she was bright, witty, smart, and beautiful. We then went on several dates over a couple months.

Jay: How did we meet?

Sara: On a dating app, obvi. Meeting in person is so 2007. To be specific though, we met on OKCupid which actually isn’t the most terrible of apps.

Me: What was your first impression of me?

Sara: My first impression of you online or in person?? I’ll just tell you both. Online – your profile actually made me “LOL.” I think you had a bunch of silly puns and I was kind of just like “is this guy for real?” If he sincerely loves puns then that is adorable and great because I often chuckle at a good pun. If he put them there ironically, also great because it likely means he is likely sarcastic and dry just like me!

Me: How did you react when I told you I was trans?

Sara: Well I was a bit surprised (*note this is a huge understatement). I honestly had no idea and may not have reacted super well at first. To be fair though, you did tell me via text while I was partying at a college reunion. Also, I believe I did tell you that I had just bought a triple, let me repeat TRIPLE, vodka tonic. So like timing on your part may not have been great.

Me: What were your first thoughts when you found out?

Sara: Hahaha lots of really uninformed things – What does this even mean? Has he had surgery? When did he transition? How does the hooking up go? Can I tell my friends? How will they react?

Me: What did I do wrong/or where could I have improved?

Sara: Overall, you weren’t awful… Just kidding! You were pretty cool. We definitely got along well. Main complaint was your inability to make time.

Me: Why didn’t we work out?

Sara: I require a lot of attention and you were essentially married to your work. Just to see you more I attended a work event or two of yours. I wanted someone that actually seemed interested and eager to spend time with me, but it did not seem like you were quite ready to make time. I am a firm believer that people make time for what is important to them, so dating (or perhaps just me) didn’t seem to be a priority for you.

Me: What were my most annoying traits?

Sara: Hmm the only trait that ever really rubs me the wrong way is being a loud chewer, and I don’t think you did that, so it was all good!

Me: And what about my best qualities? (Yep, I’m digging for a compliment—that can go under my annoying habits.)

Sara: Fun, interesting, easy to carry conversation with, and you have a dog.

Me: Would you date a trans guy again?

Sara: Yeah. I don’t discriminate in the men I date (and that isn’t really all positive). I’ve dated literally half of DC, and as one friend described me “you literally have no deal breakers. Like you’ll actually go on a date with anyone.” Yup. Accurate.

Me: Where do we stand now?

Sara: Still friends! Yay!

Me: What advice would you have given me on our first date, if we could back in time?

Sara: Our first date was fine. I mean I went out with you again after all. BUT, you should consider bringing Hazel to any and all first dates. No one can refuse a dog, and if the girl doesn’t instantly fall in love with her, then she is silly and not worth your time.

Me: And what advice would you give me for my future dating success?

Sara: Just make a bit more time for the poor girl. Otherwise no need to change. Who doesn’t enjoy a quirky, pun-filled guy?! Oh! But I would recommend occasionally sending a text with a cute animal pic or video. I hear girls eat those things up 😉

Me: What tips would you give any poor unfortunate soul who goes on a date with me?

Sara: Look up witty puns, preferably ones with funny pictures to impress him. Be flexible.

If you want to hear from more exes and their version of what happened to us, you’ll have to wait for the book. Which yes, I’m still working on getting published—it really is going to happen. I reached out to six exes including my very first girlfriend and all but one replied and none of them held back.

If you could reach out to an ex, what would you want to tell them?

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