Do I Keep Dating A Really Nice Guy? - MONDAY MAILBAG

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.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendGet $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast  

Episode metadata supplied by the publisher feed · Published Jan 12, 2026

What this episode covers

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.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendGet $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast

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Do I Keep Dating A Really Nice Guy? - MONDAY MAILBAG

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This episode was published on January 12, 2026.

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