I’m a Lesbian Who Went On A Date With A Man

A woman broke my heart. So I tried dating a man.

I’m a lesbian. And I’ve always been a lesbian, long before I even knew there was a word for it. I realized I had a crush on another girl in second grade when she shared her crayons with someone else and I was VERY jealous— not because I coveted the crayons but because I wanted this friend all to myself. Then I started developing crushes on my female teachers and librarians. To this day, I still think there’s no sexier woman than a woman in glasses and a cardigan. When I went through puberty, I knew beyond a shadow of a doubt that I am as gay as the day is long. On the Kinsey scale, I’m a solid 6.

So it is puzzling, even to me, that I decided to date men after a particularly harrowing breakup with the woman who I thought was the love of my life.

Here’s the thing: I was completely head over heels, “I want to marry you” in love with someone. We’ll call her Harriet. And Harriet broke my heart. Not once. Not twice. But three times. Yes, that’s right, I was an idiot and took her back each time until the third time when my best friend insisted that I block her on all social media, on my phone, and on email to prevent me from crawling back in a moment of weakness.

Harriet ripped my heart out, stomped on it, and then spat on it for good measure. And I thought, if she isn’t the one for me, no one is. But one day I sat in the lounge at my workplace and listened to my straight coworkers talking about their boyfriends and husbands, and I thought, Men sound so simple. So easy. So much less complicated than women. Why am I even GAY? This sucks! I had a silent pity party for my gay ass right there while I poked at the remnants of my salad and thought about how easy it must be to be straight.

And then I got perhaps the most hare-brained idea I’ve ever had. I decided to place an online personal ad to find my rebound person and pick up the pieces of my shattered heart. But instead of posting my ad as a woman seeking women, as usual, I decided to be a woman seeking men.

It felt foreign, strange, and even sort of like an out-of-body experience. Like I wasn’t entirely sure what the f*ck I was doing, but I went ahead and did it anyway. I had no idea what to say to attract men, so I kept my profile short and sweet. I said nothing about my lesbianism and lack of experience with men in my profile. I wasn’t trying to attract perverts who thought lesbians could be converted after some time in bed with them. Once I posted my ad, I told absolutely no one about it. I knew what my friends would say, and I was worried they’d think I’d lost whatever sanity I had left, post-breakup. I just couldn’t deal with their looks of pity and concern.

Within an hour of placing my ad, my personals inbox was flooded with responses from men. A lot of them were canned messages that I could tell they’d just copied and pasted to everyone.

“Hey sugar, you’re beautiful. What’s up?”

“What r u doing 2nite?”

“You’re sexy. What would it take for us to meet for a drink?”

(Insert d*ck pic here with no caption or text to accompany it)—this happened a few times.

The messages continued pouring in. And I realized that straight women may have it easier, in some regards, what with straight privilege and all, but my god… how do they keep up with all of their messages on dating apps?! I don’t even think I’m conventionally attractive for men; I look like a stereotypical lesbian. But somehow that didn’t seem to matter to these dudes.

While I immediately deleted the more sexually explicit messages, as well as any messages riddled with grammatical errors, there were a few guys with whom I exchanged some “getting to know you” messages.

One man, in particular, stuck out. He seemed genuine in his interest. Smart and kind, based on the stories he shared about himself. And he had a pretty face with long, beautiful eyelashes. I’ve never been attracted to the male body, but as the days wore on, and we continued to email and text, I tried to imagine what it would be like to kiss him. When he asked me to meet him for a drink the following day, I agreed.

I don’t think I’ve ever been as nervous showing up for a date—not even as nervous as I am when going out with really hot women who seem out of my league. With sweaty palms and shaky hands, I greeted him with a small hug. His smile eased my nerves, but I still felt like a fraud, worried I’d be discovered right away. I wore the most ‘femme’ outfit I had in my closet, which still screamed ‘tomboy dyke’. I hoped that he wouldn’t notice.

As we sat next to each other at the bar and exchanged stories about our lives, I felt unsure of how to conduct myself. I don’t know what men like, but he seemed to enjoy me laughing at his jokes, so I kept that up. As he spoke, I kept thinking about how nice he seemed but how wrong the date felt. I thought about how my mom might die of happiness if she thought there was even a hint of a possibility of me living a straight life. That thought made my stomach hurt. I felt like a fraud, laughing at this guy’s jokes while trying to hold back tears.

I hated every minute of the date, but not because the guy wasn’t interesting or nice. He seemed cool, and I could have seen us as friends if we’d met in any other forum. The beers helped me act as if I was comfortable with everything, but on the inside, I was screaming to myself, NEVER AGAIN. That’s when he reached over and touched my hand, his eyes looking for some reciprocation or indication of interest. This dude was going to expect me to kiss him—or worse, have sex with him—and that’s when I knew: I just couldn’t do it.

After two beers, I told him I had to get home because I had plans with a friend later. Though he reached for my hand as we walked to the subway station, I pretended not to see as I slipped my hands into my jacket pockets. We said goodbye, and I kept myself at an awkward distance.

vI didn’t think I’d hear from him again, but I did. He called me the following day and asked for a second date. I ignored him. He texted two days later with another follow-up, and that’s when I told him I was nursing a broken heart and had jumped the gun trying to date again. I’d heard of men retaliating and calling women nasty names when rejected, but this one didn’t. I was relieved to have been honest-ish with him rather than ghosting him.

After that date, I spent months trying to be happily single. I had to mend my broken heart, and I knew that when I was ready, I wouldn’t be looking for men. I am a lesbian, through and through, and nothing could change that for me, not even a shattered heart or thoughts of a simpler, more socially acceptable hetero life.

Lessons learned. Although being straight looks easy from the outside, and straight privilege is a thing, it’s not anything I want or need to experience in this lifetime. Straight women get a lot of unsolicited dick pics. I am 100 percent gay and will never, ever try to date a man again.

Have you ever done anything out of character after a difficult breakup? Let us know in the comments!

What Do You Think?

2 comments on “I’m a Lesbian Who Went On A Date With A Man

  • Expressing affection through gentle actions like sucking on a partner’s tongue can deepen the intimacy and connection between two individuals. It’s a tender expression of passion that transcends words, creating a unique and unforgettable bond. Such moments of vulnerability and shared pleasure contribute to the beauty of a truly meaningful connection.

    • Oliver Maryska says:

      I am a man who let’s the girl I’m with also see & have Sex with other Women without getting angry as long as I’m the only man that you see. You can have singles or more, or even include me. That’s your decision, but if we meet then this is what I have planned.


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