Going On A Date With An Old Hookup, How Do I Make It Real This Time? - MONDAY MAILBAG

Going On A Date With An Old Hookup, How Do I Make It Real This Time? - MONDAY MAILBAG

Published: April 20, 2026

Duration: 42:42

It’s Mailbag Monday, and Jared is giving advice on 👇  

Am I ruining the romance by not letting him fully handle and pay for the proposal?Reconnecting with a past hookup on Hinge, but I want it to be serious this time  Boyfriend in a wild sports group chat called the “Titty Committee” - ew

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


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