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Kaitlyn & James

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James Barrera

and

Kaitlyn O'Connor

August 29, 2025

St. Helena, CA
82 days82 d20 hours20 h41 minutes41 min3 seconds3 s

Our Story

From Cabo Clicks to Chicago Kisses: A Love Story

We met on Hinge, where Jim’s thirst trap photo from a family trip to Cabo caught Katie’s eye. Turns out, Katie had been going to Cabo every year since she was 13, so the conversation was off to a sizzling start. After some back-and-forth texting, we finally set a date. On the big night, Jim texted to confirm, and Katie enthusiastically replied, “Yes! See you at 7 PM!” Jim arrived on time and snagged a table at El Che, nervously holding off on getting a drink until Katie showed up. Ten minutes later, he caved and ordered one. Katie hobbled in shortly after, laughing about how she couldn't beat Google Maps since she hurt her knee skiing. The drinks and conversation flowed for hours, and when it was time to go home, Jim gallantly offered to walk Katie back since she mentioned she was new to Chicago and not familiar with the area. Little did he know, she lived just a five-minute walk from him! The night ended with a kiss, sparking a relationship that has now blossomed into marriage.

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