It's Monday AKA Mailbag Monday 🙌 📩Fresh off a trip to Boca for the Jewish New Year, and Jared tells us about his love for the fall season, the nostalgia of classic Halloween movies, and the joy that comes with the cooler weather. He shares why October might just be the best month of the year—no stressful holidays, still nice enough to go outside, and the perfect time to embrace everything Halloween-related🎃Then Jared shifts over to dating topics! He explores the complexities of early dating expectations. A listener writes in about her situation with a guy she’s been seeing for a few months, navigating mixed signals and inconsistencies in communication. In the listener mailbag, Jared addresses a dating dilemma about salary differences and who should pay on the first date.

Jared dives deep into the dynamics of texting in the early stages of dating 📲 He questions whether the listener is being herself or playing it safe by waiting for the guy to make all the moves. He reflects on how some people, including himself, have found themselves taking a passive approach to dating, keeping score of actions like texts and dates without showing their true selves. Jared emphasizes the importance of being authentic and upfront early on, especially when it comes to establishing expectations around consistency in a relationship.

As the episode progresses, Jared highlights the difference between expecting consistency and commitment, and how sometimes, vague requests for "consistency" can push someone away. He also discusses the listener’s experience of transitioning from casual dates to physical intimacy, and how it led to a sudden shift in behavior from her dating partner. Jared offers practical advice on how to be direct, express vulnerability, and navigate uncomfortable conversations to avoid falling into the trap of "safe dating."

We move on to another listener mailbag,  Jared addresses a dating dilemma about salary differences💰This has caused tension in their relationship. Jared says, just split it so you don’t feel this way!

Tune in for all this and more, including a shout-out to all of you writing in! continue to write in at 👉[email protected] or DM us at @jtrainpodcast

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🙋🏻‍♂️ Jared Freid

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Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

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🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

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Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

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Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/