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April 14, 2025 30 mins

It’s a Mailbag Monday and Jared’s here to help two listeners navigate their romantic gray areas!

First, a listener is stuck in a limbo with her ex, who she’s been reconnecting with after their breakup in October 2023. Although they’ve been texting consistently and even got physical a few times, she still doesn’t know where they stand. Jared dives into how she can take control of the situation and have the important conversation to gain clarity without fearing rejection.

Next, another listener writes in about lingering thoughts of a past situationship, even though she’s in a committed relationship and about to get engaged. She still checks his social media and wonders if these thoughts are signs of unresolved closure, or just a harmless curiosity. Jared unpacks what it means when a past relationship resurfaces in your mind, and how to keep your focus on the love you have in the present.

Tune in for advice on tackling those tough conversations and understanding when your past is just a memory—plus how to handle the uncertainty that can come with moving forward.

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🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

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/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/


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 se

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