Can a couple be successful in a professional and personal relationship? We’re finding out with this Sunday Special’s guests Nick and Elyse Oleksak, known for bringing their business Bantam Bagels to Shark Tank and selling for millions. The episode starts with learning how our guests came to know Jared, then J&J delve into their success and how the inner workings of their business played a role in their relationship. How do they turn off work mode and incorporate date nights? Has business been be...
Apr 07, 2024•43 min•Ep. 542
Spring is here, but while we’re waiting for the weather to catch up, we’re discussing early dating to get you back out there. An email from last week about accidental sexts reenters the chat when our first email asks about strange messages from men on dating apps. Are there really that many creeps out there, or is she doing something to attract them? The Awkward Encounter is more of a reassurance ask about where a situation left off. The next email comes from a man who met a woman IRL. He’s not ...
Apr 03, 2024•1 hr 34 min•Ep. 541
Spring cleaning time is here, so we’re heading into April ready to clean out, refresh, and reinvigorate our mindsets with the help of one of our listeners! Jeannette Cieszykowski, Feng Shui consultant and owner of Elemental Clarity, reached out to Jared after hearing a Benefits episode about how his apartment was holding back his dating life. This Sunday Special, she joins J&J to talk about feng shui, the energies we hold in our homes, and how simple changes could help us succeed in our dating i...
Mar 31, 2024•53 min•Ep. 540
It’s the Wednesday before the big weekend – Jordana’s birthday getaway and Jared’s time to shine as his brother’s best man. Before diving into the episode, they tease what they’re anticipating ahead of their travel days, then spill into Jared’s TikTok encounter and the big debate going on with Oversharing. The first email comes from a divorced listener feeling insecure about blame her ex-husband placed on her when it came to words of affirmation. Now that she’s in a new relationship, she wants t...
Mar 27, 2024•1 hr 31 min•Ep. 539
Dreams are coming true today– Jordana’s #1 guest, mental health icon, and host of “Where Should We Begin?,” Esther Perel is making this a standout Sunday Special. We get started with the existence of situationships, spill into her findings about eroticism and sustaining relationships, plus the universe affected when an affair occurs. The episode ends with a listener's email about a devolving sexual connection with her boyfriend, leading to her finding something unsettling from his past relations...
Mar 24, 2024•1 hr 4 min•Ep. 538
Spring is in the air, and we’re ready to welcome all the fun that comes with more sun and warmer weather. Before diving into emails, J&J both have exciting plans to come, plus they receive another listener’s wedding invitation! Next, they hear from a male listener who just got stood up on a second date but met someone new while he was waiting. His original date ended up reaching out, so does he owe her another shot or would it be OK to call the girl he ended up meeting instead? The Awkward Encou...
Mar 20, 2024•1 hr 6 min•Ep. 537
If you’ve cheated or been cheated on, this Sunday Special is for you. Before diving in, Jared has some pre-wedding thoughts as we get closer to his brother’s big day. Then, J&J play a round of “Petty or Prudent?” about removing social media posts with your ex. Is that an unspoken rule of breakups, or is it OK to let posts of your past stay up? Next, we hear from a listener who’s just cheated and come back to the wreckage his ex left at home after she found out. He asks Jared and Jordana how he c...
Mar 17, 2024•42 min•Ep. 536
Nature is healing this week! Jordana is tan and refreshed from her trip to St. Kitts, JetBlue made amends, and Jared brought gifts for himself! Next, a new listener intrigued by an AITA about lying to have sex with someone wants J&J’s take on consent and morality. The Awkward Encounter leads to impromptu dramatic performances. Then, J&J answer a listener email in Better With Age segment sponsored by Lee. Our 29-year-old listener has been hit hard by her breakup and, despite her ex being the issu...
Mar 13, 2024•1 hr 28 min•Ep. 535
We’re getting to the bottom of an on-again, off-again relationship in this Sunday Special! One of our listeners, Natalie, knows she’s dating a man she’s been seeing since September, but he keeps backpedaling on the seriousness of commitment. They’re in their 40s, she knows what she wants, and he claims to care for her, so what is the hold-up? When she listens to our podcast, some of Jared’s answers resonate with the way she perceives this man to be, so she wants answers from Jared and a reality ...
Mar 10, 2024•50 min•Ep. 534
J&J have a lot to discuss this week! Jordana is finally about to get her vacation fill, but it’s going to take a JetBlue flight to get to her destination. Then, Jared retells the story that his followers (and Jordana) were convinced was a meetcute, and explains why it wasn’t a romcom setup in his mind. Plus, after meeting Rob at his Boston show, Jared gives an update on our SOS caller. Next, he and Jordana are asked about the rules around your parents’ involvement in your dating life. Should you...
Mar 06, 2024•1 hr 23 min•Ep. 533
This Sunday Special is a birthday gift to Jared! Joey Grazadei, the Bachelor and the internet’s newest boyfriend, is in the studio and ready to face Jordana’s questioning. We get asked endlessly about the two types of men, so we’re putting Jared and Joey to the test. Is a single man ready to get married pretty similar to a single man seeing how it goes, or are there questions to emphasize any polarizing differences? We’re pulling back the curtain and breaking down the perfect Bachelor image to s...
Mar 03, 2024•58 min•Ep. 532
The Worst Month of the Year is wrapping up, but before it ends, we’ve got a lot of off-air moments to recap from the past week! Since last week’s recording, we surprised Jared with his apartment tour, hosted our first mixer, he had back-to-back sold out NYC shows, and now his birthday has finally arrived. Then, we hear from a listener who needs Jorge’s perspective on a guy she’s dating. Is she only uncertain because she’s used to dating Jareds? The Awkward Encounter is encouraging more listeners...
Feb 28, 2024•1 hr 22 min•Ep. 531
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-ter...
Feb 25, 2024•30 min•Ep. 530
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 men...
Feb 21, 2024•1 hr 11 min•Ep. 529
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 w...
Feb 18, 2024•30 min•Ep. 528
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...
Feb 14, 2024•1 hr 38 min•Ep. 527
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 th...
Feb 11, 2024•44 min•Ep. 526
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 rea...
Feb 07, 2024•1 hr 15 min•Ep. 525
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,...
Feb 04, 2024•49 min•Ep. 524
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 boyfrie...
Jan 31, 2024•1 hr 25 min•Ep. 523
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 ...
Jan 28, 2024•52 min•Ep. 522
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 t...
Jan 24, 2024•1 hr 19 min•Ep. 521
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 h...
Jan 21, 2024•39 min•Ep. 520
This week, J&J are coming in hot with a debate on the difference between “seeing” someone and “dating” someone. They put dating stages on a scale of 10 and, as the singleton of the studio, Jared calls it like he sees it. Next, the first emailer is preparing to meet someone from her boyfriend’s past and needs help on how to deal. But, should someone he slept with once before they met even matter? The Awkward Encounter involves a red flag revelation of a first date’s past. Then, another listener n...
Jan 17, 2024•1 hr 41 min•Ep. 519
It’s un-cuffing season and we’re talking all about whether or not it’s time break up. J&J start with a preview of their upcoming travel plans — milestone birthdays and wedding speeches are already in the works — followed by a round of “Icky or Picky?” about a hot moment gone cold. Then, they hear from a 27-year-old listener who’s concerned that she and her boyfriend are less and less involved in each other’s lives after 7 years together. Is it a case of the seven-year itch, or should their diffe...
Jan 14, 2024•34 min•Ep. 518
J&J are back in the studio for their first recording of 2024, starting with a New Year’s Eve recap and their own thoughts on Jared’s post-date episode. They hear from a listener who is five years into a dead-end relationship and in need of a breakup plan. How do you spot a “sunk cost” in your own relationship? The Awkward Encounter is a leftover from the holidays, featuring a cringe-inducing moment with a guy and his mother. The next emailer is happy in her relationship, but is having trouble ge...
Jan 10, 2024•1 hr 21 min•Ep. 517
J&J are solving couple's conundrums in today’s Sunday Special. Comedian Rosebud Baker joins the pod and gives a breakdown of the reveal that led to being engaged within 6 months, having COVID while pregnant, and how she always knew her husband would make a good dad. Then, they play a new game called “Couple’s Court” to give ruling on a sleepover issue in a listener’s relationship. They both have the same side of the bed, so isn't it only fair that they trade off when they sleep at each other’s p...
Jan 07, 2024•45 min•Ep. 516
J&J are back with a very exciting episode to ring in the New Year. Jared breaks down how he was feeling before, during, and after his blind date with a U Up? listener and how it has made him reevaluate his post-date process. Then, his date Nora joins the show to give Jordana all the details from her POV. Later, Jared rejoins the convo to review The Seville as a first date spot and chat with Nora about how he could improve his first date skills. Jared and Jordana wrap up the show with a round of ...
Jan 03, 2024•1 hr 31 min•Ep. 515
J&J are saying goodbye to 2023 with today’s Sunday Special and, from Oxford’s acknowledgment of “rizz” to Taylor Swift’s TIME honor, they’re starting off with big moments of this year. Next, they discuss dating predictions for the new year before diving in to the advice email. Our listener told her BF that she wants to be engaged by the time she turns 30, but now that the year has arrived, she’s not sure she’s ready after all. How does she talk to her SO about it without setting off alarms about...
Dec 31, 2023•47 min•Ep. 514
Twixmas time (the days between Christmas and New Year’s–it’s a thing) is here, and J&J are winding down 2023 with a regularly scheduled episode. The first email is about a compromise issue: our listener’s love language is quality time, but her husband spends several hours gaming. J&J, with input from our producer Jorge, debate whether this falls under a hobby or an addictive habit, and what it could be a red herring of. The Awkward Encounter is a gross memory with a sweet ending. Then, the secon...
Dec 27, 2023•1 hr 10 min•Ep. 513
