“I like the Bartenderrrrrrrrrrrr”: A Tale of an Awkward Writer (Me) and His Obsession with a Chicago

| Romance Columnist

I’d like to think that it’s not just I who has had an infatuation with that special bartender. Maybe it’s the fact that he knows how to make great drinks that makes him sexy. Or maybe it’s his devilish good looks. But who am I kidding? It’s this wicked combination that makes this certain bartender in Evanston, Ill. so alluring and appealing. And you know it’s bad when every time you return home from Wash. U., you drag your friends into that bar just to see that dream bartender.

I first met this certain bartender back in May, after school had let out. My friends from Northwestern still had school so we went out one night to get some drinks. My friends told me about their friend who bartends there and said that we both had a lot in common: We both were into guys and we both had at some point worked at an Abercrombie and Fitch store. I’m still not sure why these two facts proved that the bartender and I would have a lot in common, but regardless, we entered the bar.

My friends had built this guy up to sound like some kind of a god, so when I saw the bartender I wasn’t immediately struck by his beauty. Still, we ordered drinks, and my friends chatted with him. He seemed nice, and he sure did know how to make a good girly drink. Maybe it was the fact that we were there for a while or the fact that I kept drinking, but I finally started to see Jeff’s mega appeal to my friends. He was attractive, funny, a great conversationalist and he seemed like a genuinely nice person.

Fast forward to five months later: this past Fall Break, my friends from Northwestern and I went to Jeff’s bar on Friday night. Sure enough, he was working, and sure enough, he made me a great drink. But I didn’t know if I should talk to him or leave him to work. I started thinking: how do you approach someone you like when he/she is working at a job? And is that person being nice and flirtatious with you because he/she is actually into you, or because he/she just wants a good tip? It’s tricky, tricky, tricky.

The next night, the same friends and I went to the area of Chicago called Boystown, and walked into a bar. I almost died, literally, when I walked in and saw bartender Jeff sitting at the bar. True story, since I almost tripped on the step and could have fallen through a glass table. So I had a choice: I could either walk up to him and talk to him, or I could chicken out and not say anything. While I wanted to do the latter, my friends ordered me to talk to him. So I did. And we talked for about 20 minutes and I thought I had died and gone to heaven, but suddenly, some other dude comes up to him and kisses him. I knew I was in trouble at that point, and I motioned for my girlfriends to come help me. They started talking to this mystery kisser and found out that my bartender and this guy just started to “unofficially date.” So my friends and I told him we were going to walk around the bar a little more, and a little while later, Jeff came up to me and told me he was heading out but that next time I came back to Evanston I should come by the bar to say hi.

While I was totally bummed by the fact he is “unofficially dating” someone, I was proud of myself for actually approaching someone I was interested in. While I don’t consider myself a shy person anymore, around guys I freeze up, so talking to this guy was a big step for me.

If you’re like me and you find yourselves in situations where you like someone you meet, even if he/she isn’t a bartender, remember that nothing can ever result in romance without communication. While personally I like to be courted—as in I like people to come up to me and have them do the work—sometimes you have be the one to make things happen and just do it. Like Nike.

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