meeting the woman of my dreams | matt’s side of the story part 1

I had all but given up on the idea of meeting a woman through online dating, and it only was partly because of my trans situation. The thing is, men just have a pretty rough time on online dating sites because so many guys abuse the resource.

I’m not the kind of guy to make any sexual advances on a girl unless she asks for it or if I feel that I know her well enough that she would accept my advances… which isn’t true for a good number of guys online. So, being a gentleman online made me virtually invisible to most women.

Maybe Steph would be better at explaining why men are largely ignored online until a woman feels like addressing them, but regardless of the reasoning behind it, women weren’t talking with me online so I kind of just let online dating fade to the back of my mind. I probably checked it once a week, and usually because a coworker would bring it up.

I mean, not only were women not talking to be, but there was nothing on my dating profile that even alluded to the fact that I was trans. So, what happens when I actually met these women in real life and had to disclose that kind of information?  How would they take it? Yeah, at some point I figured I might just be better off meeting women through my friends, where they could break the trans news first and then we could awkwardly date and break up and so on… at least, that’s how it was going for me when I met women through my friends.

College was a little different, but that’s a story for another time.

So, I’m sitting there not caring about my online dating adventure, when I happen to log in and see that an adorable girl had messaged me. At first I’m shocked and a little worried, because she messaged me a few days prior to me seeing her message. I got over it and messaged her back on Monday the 4th of March…


As you can see, I’m super suave. Ok, I’m just a dork, but it worked out for me this one time so it’s ok.

Our messages kept getting longer and longer and by Wednesday we had a date planned for Friday evening. Dinner and wine. I was literally going to wine and dine this woman.

Now, let’s time travel and go back to a post I made on Reddit a while ago (which is actually where a lot of this all ties back to). I went to /r/AskWomen to get their advice on how I should tell my perspective dates about my trans-ness, where the line was when it came to physical interactions prior to disclosure, and those sorts of things. Based on what they all said, I decided that I shouldn’t do more than hold hands prior to telling her, assuming that I would want to continue seeing her, and to use my best judgement about coming out to her.

Back to the date. Long story short, it was pretty amazing. We laughed so much and talked about everything that we could think of. I decided that I was getting sick and tired of dating like you’re “supposed to,” so I just hung out with this woman, who I had never met before, over drinks and food. It was easy and nice and liberating to feel so comfortable with someone. Eventually she convinces me that we should walk across this beautiful bridge nearby. It’s winter in Minnesota, mind you, and I didn’t really wear a coat, but we do the walking thing and it was nice.

She started fiddling with her purse at some point, around the same time that I’m thinking to myself, Dude… you should hold her hand. Just take her hand and hold it. Come on, Matt… Hold. Her. Hand.

So, I hold her hand. We keep walking and talking. There were more than a few times where I thought I blew it on this walk, but she was still holding my hand and not beating me with her purse, so that was nice.

We walk back to her car and she offers to drive me over to mine, even though I tried explaining to her that it wasn’t that far away (secretly, in retrospect, I think she was stalling so I would kiss her).

We’re sitting in her car, doing the awkward good-bye dance and I ask her if I can kiss her. Somewhere in my mind I was thinking, screw these rules, I wanna kiss this woman. She smiled her full-dimple smile and said yes, so I kissed her.

I finally make my exit and sit in my car… and now I’m thinking that I just screwed everything up. How can I possibly tell her now that I’ve already kissed her. And what about all of those stupid things I said at dinner and everything… she’s going to think I’m a loser… and I really liked her and our date.

The drive home was other-worldly. On one hand, I had this amazing date with this amazing woman. On the other hand, I was about to have to legitimately tell a prospective love-interest that I’m trans… something I had never done before…


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