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Oliver Buchannon
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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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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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Two Sisters (and Francis) Can't Be Wrong: Meet NYC's Most Beloved Single

May 29, 2025

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4 min read

Two Sisters (and Francis) Can't Be Wrong: Meet NYC's Most Beloved Single

Meet Sky from New York City. In the romantic comedy, she's the smart, witty, adorable baker (slash financier) the main character serendipitously meets on a train and instantly vibes with...then they get split up by a cruel twist of fate (a hoard of schoolchildren taking a field trip of the MTA)...he spends months trying to find her with just the few crumbs of information he was able to glean...only to meet her a year later as the bride at his boss's wedding. Anyway, that’s Sky. But you don’t have to be that guy. Don't let your friend be that guy.

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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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She's Got Island Time For Everything But Playing Games

Apr 17, 2025

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4 min read

She's Got Island Time For Everything But Playing Games

If you think your city's dating pool is small, try dating on a small island...but that has not deterred Janna in the slightest and we can all learn from her positive aloha spirit

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Blueprint for Love: This Chicago Architect is Ready to Build Something Personal

Apr 3, 2025

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4 min read

Blueprint for Love: This Chicago Architect is Ready to Build Something Personal

In typical architect fashion he has carefully sketched and revised his plans, he has built his foundation, and now he is ready to add some flourish to his life and find a girlfriend.

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Tarot Cards & Coffee Dates: Why This Designer Believes in Real-World Magic

Mar 20, 2025

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4 min read

Tarot Cards & Coffee Dates: Why This Designer Believes in Real-World Magic

"Is the spark overrated?" Is something the tarot cards cannot answer. But we can. And we do.

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A Tale of Three Cities: Here's Hoping Atlanta Is Alice's Wonderland

Mar 6, 2025

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4 min read

A Tale of Three Cities: Here's Hoping Atlanta Is Alice's Wonderland

The hosts endorse our very own Alice because she is as hilarious and eligible as they come. We get into some heavy dating topics that will resonate with many of you, and if you are of the male sex and can listen until the very end we will give you a prize, because you will have earned it...

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