Anika Ellison, 37

Nichols Bridgeway between the Art Institute Modern Wing and Millennium Park

Are you dating anyone? Are you hitting on me? [Laughs]

I’m wondering for our annual Singles Issue. I’ve been in a happy relationship with my boyfriend for three years—but had to endure a lot of bad dates to get here.

Most bizarre date you’ve been on? The worst date I’ve ever been on: Me and this guy went to dinner at the bar at Blackbird, and a great deal of the conversation was about him being a recovering alcoholic.

And you were at a bar. And we were at a bar! It was a lot of terrible stories about stuff he did when he was drinking—and there I am having a glass of wine. I know a lot of recovering alcoholics, and this guy was not doing well with it. It was definitely uncomfortable. I was like, “Maybe we shouldn’t be here.” We never went on another date again.

Do you have a dating philosophy? I think people stress way too much trying to find the right person, then once they finally find someone they like…

They sink their claws in too deep? Exactly. I like things to happen organically.

How did you meet your BF? Randomly at a club. We started talking to each other…about leather. [Laughs] I’ll never forget that!

Leather: good icebreaker? Well, I was wearing a leather dress and he started talking about leather pants he wanted to have made. It’s funny: Our relationship outlasted the club where we met.