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Ryan Newman

Lives in: West Loop Interested in: Women When local athletes such as Jay Cutler, Kyle Long, and Brent Seabrook need to look spiffy, they head to Newman’s shop in River North for custom-tailored menswear. Besides work, the designer’s greatest love is his two-year-old pit bull, Stella. His ideal first date? “It’s always nice to go … Read more

Eric Gehrig

Lives in: South Loop Interested in: Women A recent addition to the city’s pro soccer team—he was traded in December from the Columbus Crew—Gehrig loves to spend time at the beach after practice. In bad weather, he’s all about binge-watching (he just finished Bloodline on Netflix). His type: Hardworking, fit women who stay positive His … Read more

Jennifer Novakoske

Lives in: Old Town Interested in: Men Novakoske likes to start the day with routine: Up by 6 a.m. and out the door for a run, then a stop into Elaine’s at Hotel Lincoln for her morning caffeine. “I don’t trust people who don’t drink coffee,” she says. In the office, though, Novakoske craves variety. … Read more

Victor Wasserman

Lives in: Andersonville ​Interested in: Men He may work on interiors, but Wasserman indulges in his greatest passion outside. He’s happy to pass an entire weekend working in his large backyard garden, where he grows flowers, but also okra, quinoa, and broccoli. The five-day-a-week yogi is also on a beach volleyball team, but don’t look … Read more

Ashley Bryant

Lives in: River North Interested in: Men Bryant worked on Obama’s reelection campaign as the digital director for her battleground home state of Ohio and made Ad Age’s “40 Under 40” list of innovative leaders in marketing last year. When she’s not traveling for work, you can find her relaxing at Soho House or dining … Read more

Brynn Olson

Lives in: Lincoln Park Interested in: Men Since founding her own interior design firm in 2012, Olson describes her days as “work, work and more work, sun up to sun down.” The Nate Berkus and Associates alum—she worked with him for five years—doesn’t mind the hectic pace, because no two days are alike. But when … Read more

Jana Kinsman

Lives in: Pilsen Interested in: Men The dual-business owner says she lives in two different worlds. “One where I dress up and look cute and interact with people, and one where I’m sweaty and dirty and sometimes get stung,” she says. With Doodlebooth, Kinsman draws partygoers at weddings and corporate events; with Bike A Bee, … Read more

Roger Kapoor

Lives in: The Loop Interested in: Women Don’t be fooled by Kapoor’s résumé: The Stanford- and Harvard-trained doctor, who got his MBA at Oxford, isn’t all work all the time. “I love playing basketball, if there’s a pick-up game.” He also performs standup and loves to dance—everything from bhangra to ballroom.  His type: Women with … Read more

Adelle Infante

Lives in: Lincoln Park Interested in: Men The self-proclaimed “social director” among her friends, Infante loves experimenting with new hobbies. Her latest endeavors: Horseback riding and drumming lessons. She’s similarly adventurous in the kitchen. “I like to have people over to be my guinea pigs for recipes I’ve never made,” she says. “If it turns … Read more

Rae Gray

Lives in: West Loop Interested in: Men The University of Chicago graduate has been acting since she was a kid. Her first role at the Goodman was in A Christmas Carol in 2000, and 15 years later, she just wrapped up a turn as Alexandra in Lillian Hellman’s The Little Foxes. Though Gray spends some … Read more