My friends call it “Hate Date ‘08” because the year I ended a long-term relationship with my boyfriend was the same year I decided to go on the worst dates of my life.
“You should just…just get back out there!” my friend Miles says when he buys me my third beer at this hole-in-the-wall joint in Wicker Park. Miles always knows a good hole-in-the-wall (which should have been a sign not to listen to his advice). “I date as much as possible!”
“But shouldn’t I, you know, try to just chill on my own?” I ask Miles swigging my Stella. A Cyndi Lauper song beats in the background.
“Dude. Just have fun. You’re a writer! Think of the stories you could get!”
That week I call Aaron. We’d met at a party a few weeks after my breakup. There was total flirting and he’d asked if he could take me out.
The date is at a pub in Lincoln Park when he shows up with another attractive guy. I hadn’t known it was going to be a “group thing,” but it is my first date after four years in a relationship. I am confused, but remain open and optimistic.
“Hey, Byron, this is Max.” Aaron says to me while pulling out a chair.
Max smiles and sits down.
“So, hey, nice to meet you. How…how do you know Aaron?” I ask, looking through the menu for wine choices.
“He’s my boyfriend,” Max says with a tempered glare.
That June, I decide to go out with Dan, an actor. He had taken me to an expensive Indian place in the West Loop. After loads of drinks and dinner, the tab arrives. He slips the check into his hand and says: “It’s on me!” It was over 200 dollars and I wasn’t going to argue.
“I’m just going to run to the restroom quick,” Dan says.
Dan never comes back.
Dan number two (You’d think I’d learn from Dan One) seemed like a great dude. He had a job at an advertising firm. He had a sense of humor. He also had a lot of gas. He also didn’t mind sharing that gas while in the cab, in the movie theater and while I said goodbye to him faking an early morning meeting the next day.
Ryan is cool in the sense that he meets me at the bar high as a kite and barely able to walk while calling me “Brad.”
Then there is Adam. He is hot. He is polite. He is also a thief.
“Wait… what are you doing?” I ask, watching him put a Speedstick in his coat pocket at a convenience store we stopped at for cigarettes.
“What? I need deodorant…no one cares. Why? Does this bother you?”
I leave, telling him I’m not going to jail just so his pits could smell good.
In life, most people learn after touching something hot once that they will get burned and not to do it again. But some of us, apparently, have higher pain tolerances. Finally, after five consecutive bad dates, I decided to go on a date with someone I didn’t know very well, but wanted to—myself.
