Jared kicks off Ticked Off Tuesday from Delray by inviting listeners to vent freely, then launches into his own “rich person problem” that still feels brutal: he finally plays at the legendary Torrey Pines golf course, only the rough is so tall the course basically has a “lose your ball, no penalty” rule. Next, he’s mad that junk mail now cosplays as urgent, then listener complaints keep the petty parade going. A mother-in-law’s condo is gorgeous but has “museum couch” energy, Boston tenants are stuck doing snow and trash while the owner only leaves passive-aggressive notes, and a gym busybody tries to shame someone out of their second massage-chair session. He wraps with the universal rage of car rentals.

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Jared opens Mailbag Monday from Delray with gratitude, beach energy, and a reminder that anonymous advice hits harder than biased friends. The standout email comes from a listener who went on six “pretty good” dates and can’t stop thinking about bunny-rabbit sex, being asked to fetch latkes, and having to share a single hot dog at a hockey game. Jared’s verdict is clear and funny: if it’s still only “pretty good” after six dates, that’s already your answer. He reframes dating like investing, asking whether this relationship could realistically get 10 percent better and become a life you actually want. The lesson is not that she’s too picky, but that chemistry matters more than politeness and settling only builds resentment. Classic JTrain delivers a warm hug, a reality check, and permission to move on without guilt!

Jared is on tour! 👉 jaredfreid.com

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

Get $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast

Pop Culture Thursday has Jared breaking down Ashley Tisdale opening up about toxic mom groups and why it hits home for millennial women. He also gets into Amy Schumer’s Instagram post during her divorce and what it says about body image and fame. Plus, Cher weighs in on Kristen Bell and Dax Shepard, and why trips to St. Barts make celebrity drama even louder!

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

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