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! SUPPORT THE SHOW, SUPPORT OUR SPONSORS!🙌 indochino 👉  Support the show and use code JTRAIN to get 10% off any Indochino purchase of $399 or more at https://www.indochino.com lumen 👉 Support the show and get 15% off your Lumen. Head to https://www.lumen.me/JTRAIN MeUndies 👉 Support the show and get 20% off your first MeUndies order, plus free shipping. Head to https://www.meundies.com/FEATHER GreenChef 👉 Support the show and get 50% off your 1 st GreenChef box, plus 50 free ClassPass credits. Use code JTRAINCLASS at https://www.greenchef.com/JTRAINCLASS 🙋🏻‍♂️ Jared Freid Instagram - https://www.instagram.com/jaredfreid Twitter - https://twitter.com/jtrain56 TikTok - https://www.tiktok.com/@wizardofha Website - https://jaredfreid.com/ 🎙🚊Follow JTrain Podcast Patreon - https://www.patreon.com/jaredfreid Instagram - https://www.instagram.com/jtrain 🙋‍♀️ Our Producer Venetia AKA V Website - https://www.venetiageras.com/ Twitter - https://twitter.com/venetiaageras Instagram - https://www.instagram.com/venetiaageras/ Hop on the "JTrain" with comedian Jared