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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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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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