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

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

Clay Neigher

Lives in: Lincoln Park Interested in: Women Neigher comes by his creativity naturally: His father was a writer for The Jeffersons and The Facts of Life, and his mother is an actress-turned-­metalsmith. Since moving from Philadelphia to Chicago in 2007, he’s been a voice-over artist, an improviser, a storyteller (with Here, Chicago), and a board … Read more

Lorin Adolph

Lives in: Lake View Interested in: Men As the personal chef to billionaire Sam Zell (a job he’s held for 25 years), Adolph doesn’t need to be at work until the late afternoon, so he likes to ease into his day. After a 7 am wakeup, he reads the Tribune, Sun-Times, and New York Times … Read more

Dean Casagrande

Lives in: Lincoln Park Interested in: Women An ad account executive by day and restaurateur by night, Casagrande opened Chicago’s first sit-down meatball spot in March. It’s a labor of love. “I’m Italian, and ground zero for the idea was my grandmother’s meatballs,” he says. In his downtime, you’ll find him on the golf course … Read more

Diana Palomar

Lives in: West Loop Interested in: Men Palomar is all about making connections: On the job, she’s a news station’s public liaison, and when she’s not working, she’s mentoring young women, a role she considers one of her most important. “You never know how what you say or do can impact another person,” she says. … Read more

Rob Shasserre

Lives in: River North Interested in: Women During the week, Shasserre is often on the road for work, so he fills his weekends with triathlons and boxing lessons. He’s also finishing up his MBA at Kellogg, where he met the friends with whom he founded his latest project: the seed investor group Kellogg Angels. His type: … Read more