Olivia Castellini, one of this year's Chicago Singles

It’s a rite of summer—the night Chicago’s singles come out to play at the MCA—and it’s happening this Friday: Summer Lovin’ (details below) is your chance to mingle with the city’s 20 most eligible men and women over drinks and bites from local restaurants (M Burger, The Purple Pig) while supporting stroke therapy and research at Northwestern Memorial Hospital.

Yesterday I chatted with Olivia Castellini, a 34-year-old senior exhibit developer at the Museum of Science and Industry, about what it’s like to be a member of the club and, of course, what she’ll be wearing on Friday.

The Chaser: Did you have any idea who nominated you for the singles feature?

Olivia Castellini: I did, yes, and they were wise in coming to me first before they put the nomination in. Two women I work with decided that this would just be the best thing ever. It was flattering to be asked, but I did have to think about it for a day or two. It sounded like fun, and it supports a good cause, so I was totally up for it.

TC: What do your friends and family think about the whole thing?

OC: There was definitely plenty of good-natured ribbing going on when I told them about it. My background is varied anyway [Castellini is a physicist, a part-time model, and an avid runner, among other pursuits], and they were like, ‘OK, Liv, here’s one more thing.’

TC: Any bites so far?

OC: I’ve heard from a handful of college friends who saw the story up on Facebook. In general, I haven’t heard a whole lot yet, but I imagine that’ll change by the end of week.

TC: What would be your dream way to meet someone?

OC: I haven’t gotten so picky as to think of scenarios. I met my last long-term boyfriend in a martial arts class. I didn’t think I’d meet someone while they were punching toward my head, so I guess I’m game for anything.

TC: How do you feel about meeting men in bars?

OC: It’s really hard. Bars just seem to be such a difficult place to hear people and to get a sense of who they are. It’s better to have connections through hobbies, work, or mutual friends, but I do wish the environment at bars was a little more conducive to actually meeting.

TC: If someone just happened to bump into you in a bar or a restaurant in Chicago, where might that happen?

OC: You will frequently find me on the lakefront path, running. I think I’ve decided to train for the marathon this year. I’m at football games in the fall. I watch Packers games at Will’s Northwoods Inn on Racine—a Packers bar through and through. Cheese curds and all.

TC: Been doing any wardrobe planning for Summer Lovin’?

OC: I have quite the quandary: I thought I knew what I wanted to wear, but after looking at some photos from previous years I think I’m changing my mind. There will definitely be a fashion show with my girlfriends.

TC: If a guy wants to approach you at the party, what’s one pickup line that might work?

OC: What wouldn’t work is anything too cheesy or obvious. If he walked up and had a question—maybe he’d read something about me and had a mutual interest or question—that would be a good starting point.

Summer Lovin’ runs 6/17 from 7 to 10:30 p.m. at the Museum of Contemporary Art, 220 East Chicago Avenue. Tickets are $85 in advance, $95 at the door, and $20 extra for VIP access. In the meantime, browse more photos and watch videos of this year’s group, plus get updates on former singles.

AND IN OTHER NEWS: I hear through the grapevine that a possible name for the Logan Square wine bar that would have been Smith has emerged: Telegraph. The word apparently reflects the owners’ commitment to taking staff members on educational trips to vineyards around the world, with the employees bringing back the intel they gather to the group’s Chicago establishments (Webster’s Wine Bar, The Bluebird, and, soon, this new spot)—you know, like a telegraph. Will it stick? Only time, and lawyers, will tell.


Photograph: Maria Ponce