Episode Details

This week on Mailbag Monday, Jared kicks off the show with a trigger warning for listeners, as one of the emails touches on sensitive topics related to pregnancy and abortion. If that’s something you’d prefer to avoid, feel free to skip the second email of today’s episode.

As always, Jared dives headfirst into your dating dilemmas with his signature mix of humor and honest perspective. First, he reflects on why people trust him with their deepest questions—because he’s been offering unfiltered advice for over a decade! Unlike your friends and family, Jared won’t soften the truth just to avoid an awkward moment.

A listener is stuck trying to navigate the tricky “intentions conversation” with a guy she’s been dating for a few months. Is he as interested as she hopes, or is she overanalyzing his behavior? Jared breaks down how to take control of your dating narrative and stop playing detective.

In the second email, a complex situation involving pregnancy has Jared offering compassionate yet straightforward advice on how to approach difficult conversations with a partner. After a whirlwind romance leads to an unplanned pregnancy, our listener moves in with her boyfriend only to stumble upon a heartfelt letter he wrote to his ex—a week before they met. Now, she’s grappling with insecurities about their timeline, unspoken truths, and whether she’s truly his "person."

Jared unpacks the situation with his signature humor and insight, exploring topics like post-breakup loneliness, boundaries with exes, and why clear communication matters more than detective work. Plus, he shares practical advice for addressing uncomfortable truths in a relationship without losing your sense of self.

Throughout the episode, Jared also touches on his recent experiences in Tulsa, the highs and lows of performing live shows, and how he balances career anxieties with staying grounded. Plus, he shares exciting updates on upcoming shows in Dania Beach, Portland, Phoenix, and even Australia and New Zealand!

Don’t forget to support the show by sharing it with friends, following on Instagram, or subscribing to Jared’s Patreon for exclusive weekly content like “Coffee with JTrain,” where he gives a raw and unfiltered look into his life. Don't miss this rollercoaster of emotions, revelations, and Jared’s candid take on modern dating dynamics!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉JTrainPodcast@gmail.com

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