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An Earthy Cambridge Man Turned a New Leaf in Chattanooga...Will it Lead to New Love?

Feb 6, 2025

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4 min read

An Earthy Cambridge Man Turned a New Leaf in Chattanooga...Will it Lead to New Love?

Jonny's adventurous spirit, the same spirit that had taken him to countries numbering in the double digits, told him it was time to move away from his longtime home. He applied his pragmatism and analytical brain to narrow it down to a city with a temperate climate, progressive community, natural surroundings, and a 2 hr drive from a major city. But how does he approach love? As the adventurer or the analyst?

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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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Great Love Stories Can Begin In Any Chapter: Chicago Woman Cycles The Path With Faith

Feb 20, 2025

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4 min read

Great Love Stories Can Begin In Any Chapter: Chicago Woman Cycles The Path With Faith

Vicki has been through it all. She has grown children, adoring grandchildren, a fruitful career, a community that respects her, good friends, and a strong Christian faith that is the bedrock of who she is. She is very much fulfilled. But for too long she has been a supporting character. Help us make her the protagonist...enter: romantic interest.

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On Her Eligible Résumé: Tall, Blonde, Funny, Smart, and a Graduate from The School of Casual Dating

Jan 23, 2025

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4 min read

On Her Eligible Résumé: Tall, Blonde, Funny, Smart, and a Graduate from The School of Casual Dating

Devin had us cracking up about her hot takes, like how we should have graduation ceremonies marking the passage from the casual hook-up phase of life to the dating-for- the-long-term phase--she is a brilliant journalist who values her independence, but is ready to meet someone who has also graduated...oh, and she's willing to import the right guy, duty free.

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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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Best Man and NYC Chef Wants to Be Your Main Dish.

May 15, 2025

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8 min read

Best Man and NYC Chef Wants to Be Your Main Dish.

Adam contains multitudes. Far more than a dating profile could possibly hold. A culinary artist, jam band aficionado, Botanic Garden-stroller, occasional Spanish orator, former import/exporter (like Art Vandelay, he'd say, because he's a Seinfeld fan), New Jersey born Chicago sports fan?

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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

•

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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Be a good wingman/wingwoman. Receive newsletter-exclusive features of eligible people and share with your single friends...then someday you can take all the credit at their wedding.

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