It was last year when I went on a date with this guy “Tom”. We met on OkCupid and I’ll admit, I knew what kinda guy he was from the get go. He was the asshole that thinks he’s like more hipster, more into fashion and more “Chicago” than everyone else. I wanted to vomit –but I was intrigued to get to know why this dude thought he was God. So, we go out on a date and surprisingly, we get along pretty well. He gets my self-deprecating sarcasm and appreciates my humor. After we split our tab (of course), he asks me if I wanted to go back to his place and indulge in some more whiskey. Of course my boozehoundedness agreed. We get back to his place – it’s a nice, well-kept apartment in Logan Square – typical. I'm mid-sip into my whiskey when he basically starts the moves on me and we eventually end up naked. God damn you, whiskey. Little did I know – I was now sleeping with Christen Grey. Dude was so violent, I almost had the battered women’s shelter on speed dial. His biggest fetish was bending me over his knee and slapping my ass over and over and over again. He literally said, “Tell me when it hurts and I’ll stop”. I remember looking back at him like, ‘I have to have a safeword to sleep with you’? But, I knew there were some underlying issues with this one – and it soon became evident. He was going down on me and I think I said something like “oh my god, marry me”! I mean, he knew what he was doing, but obviously I was kidding. And I shit you not, he stops mid-way, looks up at me and says, “I’m never going to get married and I’m never going to have kids”. What the fuck? I realized then I was dealing with someone who has MAJOR commitment issues. It was so awkward, all I could think was ‘just get back down there, you tortured soul’. It was quite possibly the most awkward thing that has happened to me during a sexual experience – and that’s saying a lot.
But, living in a liberal, artsy kinda neighborhood – you meet all kinds of people with all kinds of issues that make them “so much different than everyone else”. Which, in this next case, he really was different than anyone else I have been on a date with. “Jeff” and I met online as well and had a lot in common. We ended up liking the same bands and loved singing karaoke. Be still my heart! I really liked this guy. After a night of karaoke and booze, we ended up back at my place and listened to music and talked. We were talking about our past and experiences that we’ve been through. He starts alluding to fact that he likes butt play and weird shit that dudes would never admit. That’s when he drops the proverbial bomb on me. He said he’s bisexual and just last week, hooked up with his ex-boyfriend. Listen, I’m open to people’s life choices and I’m by no means right-wing kinda person, but I felt so weird hooking up with a dude who just hooked up with a dude. And I could tell Jeff really liked this dude – so I really just sat there and consoled him about his dude-on-dude break up. I hope you take this as a lesson – if your dude is alluding to butt play, there may be something else behind it (literally).