It's Chit Chat Wednesday and we have dating expert, Logan Ury! Jared and Logan dive into the complexities of dating, discussing how it can often feel situation-dependent. They explore how people’s romantic behaviors can shift based on specific interactions, with Jared reflecting on how two seemingly similar dates can result in very different outcomes. Logan suggests that sometimes we get too caught up in making assumptions, noting that people often make decisions based on incomplete information, such as whether to kiss on the first date.

Jared shares his frustration with how dating can feel like a "silly dance" of coy behavior, contrasting this with the more open and sex-forward experience he’s had on some dates. He admits feeling embarrassment when misreading situations despite being a dating expert, which leads to self-reflection. Logan offers a broader perspective, explaining that more transparency in dating would help, likening it to a process of matchmaking where a third party provides critical information.

They also discuss how dating apps give some insight, but there’s still a lack of full clarity, often leading to confusion and making people disposable. Logan encourages people to go beyond the surface, suggesting that spending more time with someone might reveal the deeper "iceberg" of their personality. Jared agrees but acknowledges the discomfort of confronting his assumptions.

The episode also includes a conversation about Jared's experiences post-Netflix fame, where he touches on the awkward dynamics of receiving invitations for drinks from fans in different cities. While Jared enjoys socializing after shows, he admits to a struggle between temptation and wanting a meaningful connection, all while dealing with the pressure of public expectations. They discuss how dating apps and first-date norms can feel frustrating or limiting, especially when personal preferences and sexual boundaries come into play.

Jared reflects on two recent dates: one that felt more sex-forward and liberating, and another where the traditional "no kiss on the first date" boundary left him feeling out of sync with his date. Logan compares this to the structure of Orthodox matchmaking, where clear communication and third-party guidance help navigate such situations, and suggests that in dating, assumptions often obscure understanding. They both emphasize that more dates and open conversations are needed, rather than relying solely on information upfront. Jared humorously touches on his life post-Netflix fame, grappling with dating expectations while on tour, where fans reach out but often misread his willingness to engage romantically. The episode also includes lighthearted moments about feeling awkward in dating ! It's a fun relatable episode that you don't want to miss!

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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 jtrainpodcast@gmail.com – 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/