It’s the Worst Day of the Year, which happens to be the day Jared Freid was born! The episode starts with reflecting on Jordana’s unhinged rant that gave today its special name and how he feels entering his personal new year. Then, Emma Willmann, host of Ask Men Anything, returns and shares revelations she's gained as a lesbian questioning men on everything. Next, they hear from a listener in need of guidance on an internal debate. After having sex with the guy she’s been dating, he casually mentions being queer, and she wonders why he would not be direct about such a big part of his identity. Is it internalized homophobia making her question a non-issue, or was there a better way to go about this conversation? Jared, Jordana, and Emma debate all sides of a relatable issue in today's modern dating world.

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Still in awe of Tracy Chapman’s reemergence at the GRAMMYs, J&J’s pre-show talk spills into the start of this Sunday Special. Next, they jump into “Petty or Prudent?” about blocking your ex after a breakup text. Do you owe them a chance to respond, or nothing at all once a breakup is done? Then, a listener explains why her boyfriend seeking therapy is a growing problem for her and their relationship. What’s appropriate to share with your partner from sessions, and when is it OK to push back on what you’re being told? It’s his therapist she has an issue with, but J&J have a bone to pick with him too.

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Happy Valentine’s Day! Today’s episode has something for everyone – lovers, new listeners, singles, and anyone struggling in a situationship. J&J have a dating challenge to share, but first, Jared kicks off with a pep talk for anyone alone on Valentine’s Day. Then, Jordana speaks on TikTok coming for her over last week’s Pookie and Jett debate. Next, a listener is starting to get back into dating, but just isn’t feeling it. Does she just need more time to get the spark back, or is there a deeper issue at play? The Awkward Encounter is an all too common issue of being on a date that isn’t a date. The episode ends in a “Red Flag or Deal Breaker” about your SO misspelling your name and thinking your friend is hot, and pranking a SO.

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As Valentine’s Day gets closer, we’re anticipating make-or-break reveals hitting a high, but there’s a silver lining: J&J explain why this V-Day is perfectly placed for single people in 2024. Next, they dive into “Icky or Picky?” about a lackluster conversation starter in the DMs. Then, the episode ends with an email about how to get a could-be relationship out of a weird place after the holidays. Communication isn’t what it was in December and our listener isn’t sure she can get them back on the right track without using “masculine energy,” but does that really matter? J&J read the texts she shared and weigh in on where to go from here.

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J&J are back in the studio and Jared is in a mood. He reads the DM that’s been stewing in his mind before they look into TikTok’s new favorite couple. Jordana unleashes her thoughts on Pookie and Jett Puckett, but Jared’s opinion changes mid-conversation. Then, the first email is spiraling over a guy she likes still being active on the apps. If they’ve had two good dates, then what the f*ck is he doing on Bumble? The Awkward Encounter comes with excuses, but J&J are not having it. Next, they read an “Are We Dating?” submission that meets the definition of complicated. The episode ends with a round of “Red Flag or Deal Breaker?” about a family death, fitness accessories, and nicknames.

Credit: TikTok @campbellhuntpuckett

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Are too many icks and options stopping you from finding love? Jay Shetty, host of the On Purpose podcast, is back in the studio with hot takes on today's dating cruxes. J&J dive into the parts of Jay we have yet to know, from his favorite drinking game to his bad days. Plus, having sat down with everyone from Kobe Bryant to Kendall Jenner and Michelle Obama on his own show, he shares insights from some of his most famous guests. Jared, Jordana, and Jay find common threads connecting their lives, and end the episode with a “Red Flag or Deal Breaker?” about a quiz our listener had to pass to be asked out on a date. 

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We’ve finally made it to the end of January, but Jordana can’t get into this week’s dating topics until she addresses the change on Jared’s face. Plus, J&J give updates on what’s going on in their lives. Then, #DatingTok is bringing up doubts for our first emailer: is it the man’s job to confirm a date the day-of, and what does it say about her if she doesn’t hold dates to social media’s current standard? The Awkward Encounter is a piss-take memory from being stuck on the road with a new boyfriend. The second email is about falling for a guy back home when the circumstances can only make it complicated. J&J talk through whether liking someone is enough of a reason to go for it in spite of the odds. The episode ends with a “Red Flag or Deal Breaker?” about briefly leaving a date, not sharing food, and photo IDs.

Photo Credit: Phil Provencio

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We’re overdue for an SOS episode so this Sunday Special, J&J are joined by Rob, one of our listeners, to talk through his current situation with an ex. He takes us through their dating timeline, the breakup, and how, two years later, she started to come back into his life via social media. Now, they’re on friendly terms, but what is this all for? To build a friendship? Reignite their relationship? And, most importantly, why is he playing along? J&J push Rob to figure out what he wants, call out the grey areas in this situation, and tell him what he needs to do next.

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It’s a debate day in the studio this week! Winter freeze is in full effect, and J&J are coming in hot with reality checks about settling and where you may stand with your situationship. The first emailer is wondering whether she should stop trying to date new guys and seriously consider settling for her high school ex. J&J play out the scenario of reaching out to an ex with the intention of rekindling. The Awkward Encounter shines a light on a weird moment that led to great sex. Then, J&J take the first submission for our new “Are We Dating?” segment. The episode ends with a “Red Flag or Deal Breaker?” about bad breath, a gross habit, and a lame first date move.

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January is slowly trudging on and J&J are already counting down to one month from now–the Worst Day Of The Year. As Jared’s next birthday creeps closer, he’s finally feeling age catch up with him. Then, a listener has a philosophical question made for the U Up? Podcast: what is “the ick” and where does it come from? The episode ends with an email about a Hinge match that went from interesting to way too intense in a matter of messages, and we have the DMs to prove it. J&J read the messages and have a request for the listener's match.

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