Mailbag Monday lands in the weird, snack-filled limbo between Christmas and New Year’s, and Jared proudly reminds you that while other podcasts are “resting,” Uncle J Train is still clocking in. He tackles a Hallmark-level dilemma about crushing on a cute, ring-free optometrist and how to shoot your shot without turning it into a LinkedIn crime scene. Then he breaks down the “fifth date shut down” question and why silence afterward can actually be a helpful answer for both people. The episode takes a surprisingly sweet turn with a one-year-later follow-up from a listener who finally said “I love you” after a divorce—and it worked—sending Jared into full sentimental mode. It’s equal parts dating advice, gentle pep talk, and holiday-season camaraderie.

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