My experience dating as a trans woman

I spent most of my life acting like a straight man that couldn't tell if a girl was hitting on me. After I started taking hormones and became more comfortable with my body, I thought I would try the dating scene out. This was an all around awful experience. Want to hear about it?

Well, the first time I went on a date with a guy, we met on OkCupid, we went for a walk in the park. I wore a cute dress and had a pink sun hat on. We had texted back and forth for about two months when he asked if we could meet up because we kind of clicked. When we first met face to face, I thought, oh no, I don't find this guy attractive at all. His pictures weren't exactly a lie, he probably just took time when taking them to get the best angle, a skill I still lack. I thought, it's fine, we're just going to take a walk and see if we vibe.

We did, it was pretty magical and ended with us kissing as it started to rain. Well, that led to adult stuff and we talked every day for about three months until friction in my life scared him off. I'm always seemingly going through a lot. He wasn't a fan, so he split, reminds me of my dad. We ended up talking a couple of times after that, but I rarely looked back. This is going to sound like a lie by the end of this story.

Then there was this other guy and I thought he had the cutest smile, we'll call him number two. We matched on OkCupid but when I messaged he never responded, so I felt like it was wishful thinking. I didn't have much self-confidence back then. I thought he was out of my league, so I chalked it up to bad luck and moved on. Until one day I saw him on Grindr with the same profile pic. I thought he was either very brave or kind of an idiot. We'll get to that, I assure you.

When we met, I was trying to do the whole polyamorous thing, and it left me kind of feeling lonely. Like, I had a group of people to talk to that I was "dating" but none of the connections ever felt real. If it's your thing, then more power to you. Well, we ended up talking on Grindr, and he offered to hook up in his car. I said, "Boy, you really know how to treat a lady." So we upgraded to an RV. I was going through a lot and told him I really just wanted a hug.

So we met behind his parents' house, I know, and he gave me the best hug I have ever had. That leads to adult stuff, as you do, and after our third meeting he asked me out, and he wanted it to be exclusive. I dropped the four people I was "dating" and we spent almost every night together, I know. Well, four months in, and he ghosts me and, after three days of no response, I show up at his parents' house. I half wanted to hurt him and half wanted to make sure he was okay. After an argument, he gave me the coldest hug I have ever had, and I broke up with him over text. I don't know if he ever got it. I sent, "Cinderella's dead" by Emiline. It's a banger, you should check it out, and break up with a guy using it. It's quite liberating.

After that, I messed with number three who called us "very good friends" when asked what we were. We were more like friends with benefits who went out on dates once a week with my kid. He wasn't friendly when he found out my mouth did more than one trick. I "broke up" with him as he was wandering off to greener pastures, I'm sure.

That led me back to number two. I didn't want to date him again, it was just adult stuff, although I was secretly exclusive to him. That went on for a couple of years until he was going through some life problems and I moved him in. We ended up dating and his problems became my problems until they destroyed my life too. So, with both of us on the street, I left my kid with my dad so he wouldn't have to experience homelessness. I got us both a place to stay with one of my friends until he ruined it.

His family paid for a hotel for us to stay at. I didn't know at the time that his family had basically given him a week to get rid of me and he did. I was on the streets by myself when number four offered me a place to stay for the night. We met when number two was trying to convince me to open the relationship up. I didn't want to, but we argued until I got mad and gave in. I cried all that night after trying to prove to the guy I wasn't broken. Mission super not successful.

I ended up in the bad part of town with a lot of unsavory folks. A story for another time. Number four wasn't allowed to have feelings for me, that's what he said, but that didn't stop me from having feelings for him. I should probably call this trauma bonding, the story. He slept with everything. At that point I was so low that I was doing the same, so no judgment.

We never really became anything although the main reason I didn't leave the area was because I wanted to be close to him. After our "emotional relationship," that's what he called it, I left because I was kicked out of where I was staying because I was no longer useful. He stalked me a bunch, and we hooked up a couple of times after that.

A couple of months later I ended up back with number two. He even asked me out again, and I said yes for some reason. We stayed in a motel together while I worked and he played on his pc. When I found out he was cheating on me, I decided to split. It's been like nine months. I heard he had a kid. I hope he's happy.

So that's one trans woman's experience when it comes to dating. I could barely get any of them to take me out on a date. I know I should have valued myself more than to jump off the deep end, but you live and you learn.