Woman seeking man Robyn Tyler Owner, All Around Housing Age: 42 From: Elwood, Illinois Lives in: River West Tyler’s company assists with relocating insurance policyholders into temporary housing after major property loss, as well as corporate relocation. She, too, is always on the go. A spontaneous traveler who jets to New York monthly, Tyler also spends … Read more
Woman seeking man Jennifer Kramer Director of entertainment and special events, Navy Pier Age: 43 From: Wauconda, Illinois Lives in: Old Town Kramer is as Chicago as it gets: The Second City alum heads the events team at Navy Pier, volunteers at Old St. Pat’s, hangs out at Butch McGuire’s, and is a die-hard Sox, Bears, … Read more
Woman seeking man Lisa Tolliver Director, Capstone Partners Age: 40 From: Sparta, Illinois Lives in: Wicker Park This investment banker helps the owners of private family-run businesses find buyers when they want to sell or raise capital and when they want to expand. Tolliver is a big believer in family ties: She has convinced four cousins … Read more
Man seeking woman Paul Jaquez Attorney, Laner Muchin Age: 30 From: El Paso, Texas Lives in: Lincoln Park Chicago transplant Jaquez landed here last June with at least one built-in friend: his bulldog, Haley. When he’s not delving into constitutional law, he tutors elementary school kids and explores the city’s restaurant scene. Longman & Eagle is … Read more
Here are the smartest, richest, funniest, most beautiful people you can meet in the summer of 2013.
Man seeking woman Rich Woo Financial representative, Northwestern Mutual Age: 32 From: Glenview Lives in: Old Town Career-minded Woo watches TED talks on business and education for fun and likes to invest in early-stage tech startups, but he also plays doubles volleyball at North Avenue Beach and recently took up CrossFit. He hopes to swim with … Read more
Woman seeking man Leah Bradford Head of philanthropy for a Fortune 500 company Age: 36 From: Pittsburgh Lives in: South Loop As a young Habitat for Humanity and AmeriCorps worker, Bradford witnessed extreme poverty, which launched her lifelong mission to improve the quality of life for others. She’s never seen Scandal, but she watches Golden Girls … Read more
Man seeking man Mike Simmons Policy director, City of Chicago Age: 30 From: Lincoln Square Lives in: Uptown When he’s not shaping the city’s path, Simmons is pedaling on it. His bikes are a tricked-out racer that he takes on the 200-mile Ride for AIDS each summer and an old Trek that he bought at age … Read more
Man seeking man Matthew Harvat Owner, Circuit Mom Productions Age: 48 From: Stillwater, Oklahoma Lives in: Ukrainian Village Harvat is an event planner, DJ, and one of the gay community’s best-known performers (he looks great in feathers). Clients have told him he’s unnervingly calm under pressure, whether he’s the opening act for the Pet Shop Boys … Read more
Woman seeking man Leslie Osborne Professional soccer player Age: 30 From: Milwaukee Lives in: South Loop and Los Angeles For the captain of the Chicago Red Stars, a fitness regimen that includes running, hiking, and yoga isn’t just part of the job—it’s a full-time passion. She may be a fashion fan who loves international travel and … Read more
