Dating Lesbians Ain't Easy

Third Time is Not the Charm

Background

Growing up religious, I imagined myself married in my early twenties (to a man, no less), with kids and dogs and jobs and cars but I'm no closer to any of it nearly two decades later. And even though I'm in love with the idea of love, I'd rather be alone than with someone who isn't my true match, and me theirs. 

Sometimes I feel perpetually single even though I've been in a number long term relationships (mostly rocky ones, for sure). And I wonder if I'll ever find the right one at the right time or if I’ve already missed my chance. Maybe it’s my “type” that’s the issue, as I tend to gravitate toward the same kind of girl as my first crush. At the time, I was teaching in South Korea and met a girl who was smart, creative and covered in tattoos. She had dark features, short hair and a stunning face. She was mysterious and her energy and confidence drew me in. For more details, see how lucky I was to Come on Out. 

But since I've moved to Chicago, my dating life has been pretty scarce, or even non-existent. It's rare I find anyone who sparks my interest, so in the meantime I've put myself out there by joining a handful of dating apps (Online Dating, Bitches) and remaining open-minded about those who cross my path.

Girl Number One

Recently, I’ve been spending my weekends out on the town drinking my nights away with friends in Boystown, Chicago. Weekend after weekend, I would see the same girl working behind the bar at our favorite spot.

One night, I had enough liquid courage to slip her my number but sadly, no response. Weeks later, I saw her again. She grabbed my attention and told me my number had gotten wet in her pocket so she wasn’t able to call me. So against my better judgement I gave her my number again. Once again, no response.

As time passed, I found myself out for a drink on a weeknight at the same bar. This was a rare occasion but one drink turned into many and as I made my way out the door the bouncer shouted at me, requesting that I go see the bartender. Slowly, I walked over to her when suddenly she jumped up on the bar, grabbed my face and kissed me. My friend’s jaw dropped.

Let's take a step back for a moment. This girl was a bit extreme, even for me. She was covered in tattoos and piercings, head to toe including her face. She threw fire for a living and cut her tongue down the middle like a snake (discovered that one later). She told me she was moving across the country in a few days and this was her last hurrah; I was in for a long night. 

We drank for hours and ended up back at her place. I woke early in the morning to her bulldog snoring between the two of us. She let me know she was late to meet her tax accountant and that, oh yeah, she had a girlfriend. They're in an open relationship. Amazing, but no thanks.

Girl Number Two

As luck would have it, I tried dating in the real world instead of online. I noticed a girl out from time to time but she was always joined at the hip with her girlfriend. Assuming that was that as far as opportunity goes, I befriended the two of them.

After months of small talk, one night she showed up at the bar alone. She approached me and came on strong. Near the end of the night we kissed, as her friends eagerly watched on. That night, I was smart enough to get in a taxi home but as we continued to speak I learned she and her girlfriend were in fact, not broken up. However, things were rocky and she’d informed her partner that she’d be exploring on her own.

Against my better judgement, I saw her once more. It was a weekday evening and she did her very best to booze me up. In some fantasy land I thought she’d be a good human and break up with her girlfriend at this point, or the other way around, hello, but no luck. 

In the end, I was so disgusted by her behavior that we stopped speaking. And get this, the worst part is that to this day every time I see her out she tries to speak to me as her girlfriend stands on watching. Yes, they're still together.

Girl Number Three

Let's try online dating. OKCupid will do the trick or was it Tinder? Anyhow, I met a girl. She was cute and fairly young. Usually I don't mess with young but she seemed to have herself together. We chatted a bit and decided to meet for a drink on Saturday night. 

Saturday night arrived. The two of us met up. Conversation was great and I was enjoying myself. We were laughing and the drinks were flowing. At the end of the night I learned she lived out of the city so I offered her a place to stay. 

It was late and we were tired, so bedtime it was. Sometime around 3 a.m. I woke to a strange noise. Half asleep, I opened my eyes to see her hovering over my hamper. I asked if everything was okay, if she needed water or the bathroom. Nope, she was fine. I heard a snap.

Something didn't feel right so after she fell back asleep I went over to my hamper. I poked around and noticed something wet. I sniffed. It smelled. It didn’t take long to realize she had peed all over my hamper, full of dirty clothes. It was everywhere. Soaking wet. I carefully pulled all my things to the laundry, cleaned up the floor and reluctantly hopped back into bed. 

In the morning, she woke and grabbed her shirt off the floor, commenting, "Oh it's still wet from the rain last night." Uhm, no girlfriend. It's wet from you peeing all over everything.

She put on her shirt and left and I’ve never heard from her again. Maybe she couldn't bear the shame.