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Hopeful season is on the horizon, but for now, J&J are getting you through the bleakest part of winter with another Sunday Special! The episode kicks off with a round of “Petty or Prudent?” about a V-Day breakup. Is it automatically petty to break up with someone on Valentine’s Day, or was our listener within reason? Next, J&J hear from a listener whose biggest issue with her talking stage is the repeated breaking of her boundaries. Is her perspective skewed from being recently out of a long-term relationship, or is this guy being f*cked up? J&J read the texts and weigh in on why these red flags should be a deal breaker. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana (and the whole team) just surprised Jared to fulfill our 10K YouTube apartment tour promise, and there was no better way to wrap than to record a Benefits episode from his couch. Taking in everything Jordana had just seen, they tease the YouTube video to come and discuss the pros and cons about his current state of living. Jordana shares what she thinks is missing and why she wants more for Jared. Jorge and Candice chime in to close out the full U Up? family having a moment. Plus, Jared comes to terms with what his next steps should be as he prepares to move in the coming months.

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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.  Learn more about your ad choices. Visit megaphone.fm/adchoices

The worst month of the year (according to Jordana) has begun, so to make February a little brighter, we’re giving Benefits subscribers another lightning round! We got questions directly from Instagram for J&J to dive into the random curiosities you have about their lives. They talk romantic gestures, what advice they could’ve used 10 years ago, and more.

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices