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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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Yes, And He's A Boat Captain. Meet Chris: Chicago's Most Adventurous Comic.

Jan 6, 2026

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4 min read

Yes, And He's A Boat Captain. Meet Chris: Chicago's Most Adventurous Comic.

Chris is adventurous, romantic, spontaneous, thoughtful, and downright adorable. He is a modern day pirate - the friendly and charming Great Lakes variety you can bring home to mom.

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Meet Torrie: She's Designing Cities for Flying Taxis (And Looking for Someone Grounded)

Dec 4, 2025

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4 min read

Meet Torrie: She's Designing Cities for Flying Taxis (And Looking for Someone Grounded)

Torrie is, like, Jeanne Gang-level brilliant, she has achieved so much already and is just getting started - and while someone like that could come off as intimidating, Torrie is super warm and generous of spirit. She can solo travel or throw a wine party that requires old friends to bring new friends. How about we show up to the next wine night with a good dude for her...

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Meet Garrett: The Midwestern Gentleman Who Will Make You a Regular

Nov 24, 2025

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5 min read

Meet Garrett: The Midwestern Gentleman Who Will Make You a Regular

Garrett has all the great aspects of a Midwestern guy: friendly, loves college football, straightforward, funny, down-to-earth. He's also so damn worldly and interesting - just ask him about his just-for-kicks culinary education in Italy. He's a man with many passions: euchre, restaurants, political thrillers...it's no wonder that he's looking forward to sharing life's bounty with a special someone. Could that be you? Your sister? Cousin? Co-worker?

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She Turns Ancient History Into Comedy Gold: Meet Chicago's Kate

Nov 17, 2025

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4 min read

She Turns Ancient History Into Comedy Gold: Meet Chicago's Kate

Kate has the kind of sharp wit that often originates from a deeply curious mind - which tracks because she mastered in museum and artifact studies after developing an interest in World Fairs. This was such a fun interview that we have invited Kate to come back and guest host...

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Seeking Mosh Pit Companion for Chicago Metal Maven

Nov 4, 2025

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4 min read

Seeking Mosh Pit Companion for Chicago Metal Maven

Aurora shatters the Gen-Z/Young Millennial stereotypes. She, like many of her peers, is out there attending concerts and meeting friends: new and lifelong. And contrary to wild notions held by our tech overlords (that the future of dating should be in the hands of our AI assistants), she would love to meet someone in the wild, because having an AI text your date back for you is soooo NOT. METAL.

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Intention Over Algorithms: Chicago's Fashionista Who Plays the Long Game

Oct 15, 2025

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4 min read

Intention Over Algorithms: Chicago's Fashionista Who Plays the Long Game

Danielle is smart, sensible, stylish, self-assured--like a modern, Palestinian-American Jane Austen character, she is not out there looking for her Arab-Christian Darcy. Instead, she's enjoying life, conquering the finance world, building a fashion content brand...but if the gentleman were to come around, she would take his call.

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Let's Hear Some Illinoise For Chicagoland's Hottest Catch

Oct 7, 2025

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4 min read

Let's Hear Some Illinoise For Chicagoland's Hottest Catch

Meet YJ. He's a media personality who is captivating because he is relatable...and he has TAKES. Controversial ones. Such as: Aurora is Chicago...or just call it Aurora-Chicago, if you prefer. And even though he's a well known community figure - a man of the people - he is looking for that special someone who won't mind him gushing about her to his fans and followers. Green flag!

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