U Up?

Before we dive into another peak dating season, it’s time to ask yourself what you want and why you need it. In today’s episode, we hear from a few listeners going through frustration and anxiety, but first, you’ll never guess what Jordana has to do. Then, J&J hear from a 32-year-old listener who is convinced that at this point, she and other women are doomed in today’s dating society. Jared levels with her, but before we let her take everyone down too, our hosts discuss the importance of what you want your story to be. The Awkward Encounter is a confusing situation phoned into our hotline. Aligned with second-guessing from the previous two, our next emailer is dating someone, but she’s not sure she made the right call backing out of a date if it would mean meeting some of his family members. Does that mean they were taking the next step, or is she making a movie night more than he meant it to be? The episode ends with a “Red Flag or Deal Breaker?” about a third-wheeling puppy, revealing a potential deal breaker before the date, and lifestyle changes. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 beneficial to their marriage dynamics? And what the f*ck happens if they were to split? Nick and Elyse open up about the personal elements behind the personas that made a life-changing deal. For more about our guests, read “A Shark Ate My Bagel,” by Elyse Oleksak (@elyseoleksakofficial), available here: https://amzn.to/3QaN6PR Learn more about your ad choices. Visit megaphone.fm/adchoices

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 attracted to her now, but she seems cool and he saw an old pic of her, so would it be wrong to date her with a secret mission of turning her into his physical type? The episode ends with a “Red Flag or Deal Breaker?” about first date convenience, refollowing an ex on IG, and body counts. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 intentions. Learn more about Jeannette's work at elementalclarity.com or follow her on Instagram @elementalclarity Learn more about your ad choices. Visit megaphone.fm/adchoices

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 to do better, but how do men like to be complimented in the first place? The Awkward Encounter validates a recent “Red Flag or Deal Breaker?” about a surprise strand of hair. Next, the “Are We Dating?” submission may be a case of overthinking a man’s removal of Bumble. The episode ends in a “Red Flag or Deal Breaker?” featuring texts about a strange favor, women with successful careers, and recovering from sending a sext to the wrong person. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 relationship. Should she confront him with what she found? J&J ask how Esther would advise, and you may be surprised to hear her answer. Find Esther Perel on Instagram @estherperelofficial or listen to her podcast, Where Should We Begin Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Encounter is why you never go back for seconds on Hinge if it didn’t work out the first time. Then, the “Are We Dating?” submission comes from a divorcee exploring the dating world. Her email stumps Jared because it’s a bit of a role reversal from what we usually hear, so J&J need your help landing a decision. The episode ends with a “Red Flag or Deal Breaker?” about seating choices, smelly genitals, and a potentially common risk when dating a teacher. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 can apologize and what next steps he should take from here, but they think he’s missing something if he truly wants to change. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 issue, can’t see herself finding love again. The episode ends with a “Red Flag or Deal Breaker?” about TikTok pranks, free drinks, and chin hairs. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 check from Jordana. Is he just not that into her, or does he just need some more time before he gets tired of playing games? J&J give her some perspective to see a future for herself on the other side of this relationship, and help Natalie draft a text to follow up on their most recent hangout. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 wait for labels or a certain time to let them know you’re seeing someone new? The Awkward Encounter proves that some men never change. Then, we receive an “Are We Dating?” submission that ends with J&J drafting a text for our listener. The episode ends with a “Red Flag or Deal Breaker?” about dating types, app omissions, and a pet portrait. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 see who the real Joey is. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 to join in on our dating challenge. Next, there’s an update to the “Are We Dating?” email from Valentine’s Day. The 95% girlfriend heard our advice, acted on it, and let us know what happened next. The episode ends in a “Red Flag or Deal Breaker? about a black eye, Valentine’s Day card, and yet another story about peeing in weird places. Learn more about your ad choices. Visit megaphone.fm/adchoices

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