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He Studied the Stars. Now He’s Looking for Something a Little Closer to Home.

Apr 15, 2026

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4 min read

He Studied the Stars. Now He’s Looking for Something a Little Closer to Home.

He manages buildings for a nonprofit that runs a food pantry and addiction recovery programs. He built his own computer at 12 and is still upgrading it.

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The PICU Nurse Who Reads Novels, Cooks from Scratch, and Is Done with the Situationships

Apr 8, 2026

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4 min read

The PICU Nurse Who Reads Novels, Cooks from Scratch, and Is Done with the Situationships

She’s a hopeless romantic who’s still optimistic.

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From Kandahar to Cape Town, Marc Has Done It All — Except This

Apr 1, 2026

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4 min read

From Kandahar to Cape Town, Marc Has Done It All — Except This

Retired diplomat, world traveler, and South Side native ready to share life's greatest adventure

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He Measures Risk Professionally, Takes Chances Personally: Meet Chicago's Riley

Mar 25, 2026

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4 min read

He Measures Risk Professionally, Takes Chances Personally: Meet Chicago's Riley

Chicago actuary, five years sober, seeking someone who makes time disappear

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Committing to the Bit: Charlsie Has Prompts For Your Opening Lines...

Mar 19, 2026

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8 min read

Committing to the Bit: Charlsie Has Prompts For Your Opening Lines...

Charlsie is a curious, funny, and kind writer in Chicago. She’s looking for someone equally intentional positive—bonus points if you already know what you’re going to be for Halloween.

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Megan Okonsky
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He Dresses Bold and Loves Boldly: Meet Chicago's Azra

Mar 12, 2026

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4 min read

He Dresses Bold and Loves Boldly: Meet Chicago's Azra

And his love language: creating playlists that span generations and genres, moods and auras.

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Cemetery Larry: The History Buff Who'll Make You Laugh Among the Tombstones

Mar 3, 2026

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4 min read

Cemetery Larry: The History Buff Who'll Make You Laugh Among the Tombstones

Larry will ghost you...but in a good way.

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Want to Cross a Trip Off Your Bucket List? Slide Into Sierra’s DMs.

Feb 26, 2026

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11 min read

Want to Cross a Trip Off Your Bucket List? Slide Into Sierra’s DMs.

Sierra brings the adventure wherever she goes. She's a writer, dreamer, theatergoer, and all around CATCH.

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Megan Okonsky
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Researcher, Storyteller, and Now Official Chicagoan. Meet Alexis.

Feb 6, 2026

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4 min read

Researcher, Storyteller, and Now Official Chicagoan. Meet Alexis.

Alexis is an excellent date - we would know!

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Ready for Wimbledon? What About Shark Diving? Meet Jeremy: The Traveler in Chicago Who’s Up For Anything

Jan 30, 2026

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10 min read

Ready for Wimbledon? What About Shark Diving? Meet Jeremy: The Traveler in Chicago Who’s Up For Anything

Jeremy is driven, kind, and an intentional citizen of the world. He wants to experience all that life has to offer—and he’d love a partner to join him on his adventures. If that means he has to learn how to sleep in, he’s willing to try hitting the snooze button.

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Megan Okonsky
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Diner Dates and Deep Conversations: Meet NYC's Anil

Jan 22, 2026

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4 min read

Diner Dates and Deep Conversations: Meet NYC's Anil

Anil splits his time between NYC and the Hudson Valley, and this aspect of his lifestyle reflects him, really: dynamic, creative, curious, forward-thinking...and at the same time, thoughtful, introspective, sentimental.

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Want a Cookies Table & Prop Bets At Your Wedding? Meet Zach: Austin Comedian with Pittsburgh Roots

Jan 15, 2026

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11 min read

Want a Cookies Table & Prop Bets At Your Wedding? Meet Zach: Austin Comedian with Pittsburgh Roots

Zach is loyal, hilarious, and creative. He shows that he cares in silly and sincere ways—the perfect balance for someone looking for a lifelong partner.

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