U Up?

This episode is full of red flags and awkward moments, starting with a guy in his late 20s unsure of how to give green flag energy. Before diving in, Jordana is celebrating her husband’s birthday soon so they discuss thoughtful gifts and Jared plans a date for them. Then, a listener asks how to show girls he’s interested without being overwhelming or pushy. The Awkward Encounter is a truly wild escape from “the Bear.” Next, a listener is struggling with her partner wanting to abstain after they already had a child. They’ve successfully parented for a year now, so where is her ring? The episode ends with a “Red Flag or Deal Breaker?” about rating your SO, mixed messages, and a date at a membership lounge. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are unraveling relationship problems, from an impending fight to a friend wondering whether she should voice how she really feels about her bestie’s latest relationship. Before diving into emails, J&J caught up about Jordana’s double date and Jared’s time spent with older singles in Boca over the last weekend. Next, they weigh in on a “Couple’s Court” about whether it was weird that our listener’s boyfriend revealed he still had access to his Bumble months after they’d been exclusive. Jared and Jordana come to differing conclusions from the emailer, plus Candice interjects with a third possibility. The episode ends with an advice email about a listener concerned with her friend’s serial dating pattern. She’s built the case on why she should and should not voice her opinion, but leaves it up to J&J to ultimately decide where she goes from here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Before diving into emails, J&J get caught up in the sitcoms of the 90s. Plus, they follow up on a recent "Petty or Prudent?" after a YouTube comment schools them on the difference between kinks and fetishes. Then, the first email comes from a listener concerned her guy friend’s intentions may be more flirty than friendly. The Awkward Encounter will make you think twice about where you hide your sex toys. Next, a listener is her boyfriend’s first girlfriend and that’s been noticeable as their relationship continues, but how much onus is on her to help him mature? The episode ends with a “Red Flag or Deal Breaker?” about whether kissing gay friends counts as cheating, a traveling quirk, and a lack of boundaries with coworkers. Learn more about your ad choices. Visit megaphone.fm/adchoices

This Sunday Special is a dream brunch group as J&J are joined by Keltie Knight, Becca Tobin and Jac Vanek of The LadyGang podcast. They start with learning the famous toxic ex origin story behind The LadyGang’s formation before J&J get into relationship icebreakers and questions that will tell you exactly how everyone’s relationship style differs. Then, they play a round of Firsts and Worsts, for a lightning round catchup on The LadyGang’s past and present relationships. Plus, Jared is outnumbered being the only one both single and male in the chat. Keltie, Becca and Jac each share differing marriage dynamics and perspectives on their past, and Jordana relates to one more than anyone else. The episode ends with a “Petty or Prudent?” about a male listener on the brink, wondering whether he should skip being his girlfriend’s wedding date to avoid being part of her family’s memories if a breakup will happen any day now. Learn more about your ad choices. Visit megaphone.fm/adchoices

Long intro lovers, today is your day! J&J have a lot to unload this week, from the one quality Jordana’s husband isn’t in love with to Jared’s weekend in the Hamptons with Hannah Berner, and a one-and-done take on this season of Love Island USA and that Casa Amor shakeup. Next, J&J get an email from a listener four years into her relationship and itching to know whether I do’s will ever be in their future. The Awkward Encounter is a trip down memory lane. Then, a male listener writes in wondering how his female coworker is getting so much attention on Hinge (no offense). The episode ends with a “Red Flag or Deal Breaker?” about changing dating app photos, misused prompts, and an uncomfortable date. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re deep into summer and Jared’s in a bit of a rut. He talks Jordana through where his mind’s been while he’s been on the road. Then, they kick off the Sunday Special with a round of “Icky or Picky?” about a secret kink. Our listener stumbled upon her date’s Reddit and saw his activity in fetish communities online and, after witnessing what he was into, she felt turned off. Next, J&J answer an email seeking redemption for revenge. Our listener is happily married, but still pining over the perfect way to tell her ex off. Jared and Jordana speak about the attempt at winning in relationships and seeing beyond the traumas of the past. Learn more about your ad choices. Visit megaphone.fm/adchoices

Double-standard debates in the dating world are weighing on us today, specifically those that are more of an issue for women than men. Before diving into emails, Jared and Jordana discuss the backlash to a Forbes article, “Are We Still Not Ready For A Mixed-Weight Romance On Screen?”, and the topic of mixed-weight relationships in general. Next, the first emailer wants to know how to let a guy know that you aren’t interested in hanging out when you still have to work – or be stuck in some capacity – with him. The Awkward Encounter is a dating don’t when you’re feeling anxious. Then, the second emailer needs help navigating her way out of a sticky situationship. The episode ends with a “Red Flag or Deal Breaker?” about prolonging the talking stage, living with an ex, and leaving out an important detail post-sex. Learn more about your ad choices. Visit megaphone.fm/adchoices

After Jordana dished on some UK setbacks, it’s Jared’s turn to share what happened after he left Cannes including a scary solo travel experience en route to Ibiza. Plus, Taylor Warning: Swifties may not like what Jared has to say about Travis Kelce's Eras Tour cameo, but if you take Taylor out of it, he’s got a point about the dire state of today’s dating world. Next, J&J receive a Couple’s Court asking them to decide if it’s fair for a listener’s fiancé to hire a stripper for his bachelor party despite her discomfort. Then, we receive an email about dating non-negotiables. A listener’s booty call keeps mentioning his “list” and, while she’s not interested in seeing him seriously, her curiosity is getting the better of her. Jared and Jordana break down what is wrong with this scenario, and the sign that she needs to walk away. Learn more about your ad choices. Visit megaphone.fm/adchoices

Listeners are in for a double rant to kick off this week, but if you thought it’d be from Jared, guess again. After Jordana gains a new commercial enemy, Jared makes a request to single listeners for this 4th of July: take advantage of the fun holidays. The first email comes from a confused listener after a man drove 3 hours to surprise her and quickly lost interest after. The Awkward Encounter comes from a single mom who met a man in France, but had to work through logistics for a hookup while traveling with her daughter. Then, the next emailer is worried she’s scaring men away by being too upfront about what she wants. The episode ends with a “Red Flag or Deal Breaker?” about men in thongs, annoying sayings, and changing thermostats. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re balancing out the seriousness with a lot of laughter as comedian Rachel Feinstein (@rachelfeinstein_) joins J&J on the pod for this Sunday Special. She’s married to a firefighter, but didn’t mean to be, so she recounts bad dates, awkward dumpings, and the lessons learned from dating through her 30s that got her to find the right guy. Then, J&J read a “Petty or Prudent?” about wanting custody of a neighborhood after a breakup. The trio discuss post-breakup boundaries, both physical and emotional, as well as whether our listener or her ex were in the wrong.For more from this episode’s guest, visit rachel-feinstein.com or follow @rachelfeinstein_ on Instagram! Learn more about your ad choices. Visit megaphone.fm/adchoices

Let’s get vulnerable! This week’s episode is full of listeners reaching out regarding intimacy, awkward conversations, and heavier topics. Before they get into it, J&J delve into differing life stages after Jared hears from a friend in full dad mode. Then, the first email comes from a male listener whose relationship seems to be teetering into the friend zone after 2 years with his girlfriend. The Awkward Encounter includes a throwback to a memorable Awkward Sex Encounter from July 2019. If you ever wondered what happened with Tampon Guy and the mortified woman who wrote in, she’s back with an endearing update! The next emailer asks how to disclose diagnoses affecting your life when you’re dating. She’s dealt with anorexia for a decade, but when does that get brought up if she wants to get serious with someone? The episode ends with a “Red Flag or Deal Breaker?” about coupled U Up? listeners, pet parents, and a common Hinge question. Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s an extra special Sunday because we’re letting you in on some office goss. Divya, a Betches staff member, joins J&J for a debrief about her neighbor. She met a cute guy in her building during cuffing season and, at the time, Jordana warned her that dating a neighbor is a risky move, but also gave some helpful advice on how to proceed. Now that summer is in full swing, J&J are dying to know if the risk was worth the reward. She retells how the situation came to be, the dates they shared along with in-the-moment advice Jared and Jordana gave, and how it all ended. With that situation in hindsight, Divya, Jared and Jordana reflect on the red flags, and J&J share what would’ve worked to spare the issues. Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are questioning narratives today, starting with what happened to romcoms. After seeing Jared’s criticism of “Anyone But You,” Jordana wants to discuss thoughts on Sydney Sweeney, Glen Powell, and the state of romcoms in 2024. Then, we hear from a listener who can’t figure out how to get a guy out of Instagram DMs and into exchanging numbers. Their mutual friends advised her that he’s just “playing it cool,” but it’s starting to feel intentionally avoidant. Next, J&J receive a long email that’s both Awkward Encounter and an ask for advice after a guy friend professed his love at the airport. Our listener is pansexual and feels a tinge of betrayal with her confusion, but J&J don’t think she’s seeing enough of the other side. The episode ends with a “Red Flag or Deal Breaker?” about texting habits, hating travel, and wearing the same shirts. Learn more about your ad choices. Visit megaphone.fm/adchoices

The perfect episode to tune in ahead of a Father’s Day brunch, J&J are back with another bite-size Sunday Special. They start with a “Petty or Prudent?” about sending an obituary after someone ghosts you, but they also saw a red flag before our listener got to the point of being ghosted. The episode ends with an email about another TikTok dating trend. Several fun #DatingTok videos are telling single people to try dating with an expiration date, but our listener didn’t have fun with the concept at all. Is it just not for her, or did she do it wrong? The hosts weigh in and advise the workaround for her and anyone else wanting to give this a try. Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are tackling nuance in the modern dating world. Before jumping in, Jordana recounts her Sonoma vacation and her driverless ride reminds Jared of dating apps’ impact on society. Plus Jared has feedback for a fan that shot her shot for an upcoming tour date, and his reasons for what was wrong with her approach tie into the first email. A listener has a crush on her fitness instructor, but is there a way to shoot her shot without making it awkward if he wants to pass? In true U Up? fashion, John Mayer enters the tangent fray, but first, J&J have an introduction to make. Then, the Awkward Encounter involves a situation going from flirty online to uncomfortable irl when a listener finally meets her colleague at graduation. Next, J&J answer an “Are We Dating?” about a long-distance connection growing between traveling work trips. The episode ends with a “Red Flag or Deal Breaker?” about seatbelts, professional Tinder pics, and IG explore pages. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are getting pumped for their trip to Cannes, but they have to get a few things crossed on their list before they go. First up, Jordana needs answers on what the f*ck is up with Jared’s beard? Next, they read a wedding note from a subscriber before delving into a “Petty or Prudent?” about a SIL asking to share a wedding anniversary date. The episode ends with an advice email for a listener’s mom. He’s tried helping her navigate dating after her divorce, but she has excuse after excuse on why no one is right, so he needs help from J&J on how to get through to her. Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are taking on complicated relationships and realizations in this week’s episode, but first, they catch up on Jordana’s latest trip, get excited for their voyage en France, and Jared vents about the unknown era he’s navigating. The first email comes from a listener looking to collect $1,000 her ex owes her. He’s gone radio silent and it’s been a year, but J&J think she’s making a mistake with her ask. Then, our final “Friends to Lovers” submission takes a turn when a listener found her lover’s Grindr messages. TRIGGER WARNING for our next email, we talk about animal abuse. J&J receive an email about an impending breakup, a heartbroken woman, and her dog at the center. She thought he was “the one,” but her dog’s reactions as their relationship progressed caused major issues, and Jared thinks her concern and focus are in the wrong place. The episode ends with a “Red Flag or Deal Breaker?” about dating your ex’s twin, tattoos of faces, and a questionable bachelor party game. Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are joined by Olivia O’Brien ahead of the release for her upcoming EP, “Love and Limerence,” but before they get started, Jordana and Olivia fill Jared in on what limerence means. Then, Olivia shares the struggles with being vulnerable in her songwriting and dating other public figures, and Jared can relate for why he’s cautious with the real experiences he puts into his work. Plus Olivia shocks J&J with the aftermath of her song with gnash, “i hate u, i love u,” blowing up on the charts in 2016, they talk double standards of women being vulnerable, the difference in LA and NYC social scenes, and why Gen Z might be more open to casual relationships. The episode ends with answering a listener’s email about being on the hook and not knowing whether she should just walk away before she gets hurt. She’s been happily seeing someone for two months, but he’s now up for a job that would take him overseas indefinitely. They have yet to DTR, but she’s certain she doesn’t want to juggle a long-distance situation. Jared, Jordana and Olivia weigh in. For more from our guest, listen to “Love and Limerence” by Olivia O’Brien (@oliviaobrien) on June 21. Learn more about your ad choices. Visit megaphone.fm/adchoices

The pod is buzzing this week, and we’re starting with Jordana’s NBA experience seeing the Knicks play (and lose) Game 7 against the Pacers reminding her of a relationship falling apart and Jared’s fired-up morning after a workout. After catching up, they jump into an email from a listener reeling over getting stood up. She had an online relationship with a man in another state for 8 years, but when the stars aligned and she found herself in his area, he blocked her. Is she wrong for wishing he would’ve communicated he didn’t want to meet anymore, or does he not owe her anything because they’d never physically met? Next, we get another “Friends To Lovers” submission from a Canadian man about a woman he met in a workout class. Afterward, a military man asks how to navigate dating when his career’s constant moves have been the subject of several breakups. The episode ends with a “Red Flag or Deal Breaker” about white lies, jorts on a plane, and a special update from a fan-favorite milk debate from our 2020 episodes. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week’s Sunday Special delves into boundaries, appropriateness, and perception, but first, J&J are catching up with Emma Willmann (@emmawillmann). The conversation from Emma’s last time on the pod gets a quick update with where it continued with a sex therapist on Emma’s podcast, Ask Men Anything. Then, Jared needs the insight of women he knows for his latest TikTok finds. Next, a male listener thinks his personality is to blame for his lack of dating life. He’s friendly and chatty, but the consensus of his friend group is that these characteristics could be “gay-coded,” so is the solution to become closed off? The episode ends with a “Petty or Prudent?” about a breakup reaction after our listener comes out to her boyfriend as queer, but it’s not the reaction to her sexuality that she’s concerned about. Jared, Jordana and Emma add some extra layers of perspective she may be looking past. Listen to our last episode with Emma, "Was This A Red Flag Or Is My Internalized Homophobia Showing?" from February 21. Listen to Emma's follow-up conversation on Ask Men Anything, "Asking Dr. Justin Lehmiller Anything" from February 27. https://youtu.be/AMPqjOcuAg8 Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, J&J are finding the balance in a few debates, from ideal thermostat temps to awkward callouts. The first email asks if there’s a limit to how much an ex is brought up during a date. Jared and Jordana don’t initially agree and weigh both sides of the conversation. Next, in a segment sponsored by Netflix, they get a “Friends-To-Lovers” story submission that's out to motivate other listeners to make a move. The second advice email is looking for the line between going for what you want and seeing what the person you’re dating is willing to do. There could be truth to “If he wanted to, he would,” but doesn’t that go both ways? The episode ends with a “Red Flag or Deal Breaker” about being overly communicative, being put in an awkward situation pre-date, and disagreeing about the best sex you’ve ever had. Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are jumping right into this week’s Sunday Special, kicking off with an “Icky or Picky?” about a delayed Hinge response. Our listener’s match explained that he took so long to get back to her because he only likes to focus on one match at a time, but she can’t decide if it’s unfair of her to be put off or if that was indeed too much too soon. Then, they get an email from a listener struggling to forgive herself for giving her ex a second chance despite problematic circumstances. J&J discuss who she's really mad at and what needs to change so she can move on in peace. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re talking guilty pleasure shows, that time Jared almost experienced death by pizza bite, and wedding planning ahead of jumping into the episode. Our first email comes from a listener dreading an upcoming wedding knowing they’ll be single, without a plus one, and only know two other guests on an acquaintance level. Then, we receive a “Friends-To-Lovers” story submission in a segment sponsored by Netflix, and this one takes a turn. The second advice email comes from a gay listener in his late 30s looking for long-term love and frequently finding short-term romance. He’s been quick to cut things off once he realized he and his dates weren’t looking for the same thing, but is he missing out on great experiences by doing so? The episode ends with a “Red Flag or Deal Breaker” about sleep farts, childhood homes, and splitting the check. Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode is all about communication and honesty, but it’s not addressed in the usual way. First, Jordana fondly remembers her go-to first date question that she’s no longer allowed to ask. It may have ruffled feathers and ruined a friend’s date, but it gave her all she needed to know to engage with someone early on. Then, J&J play a round of “Petty or Prudent?” about a listener’s reaction to her husband’s ex. Our listener was fine with a filmmaker ex keeping in touch with her husband until his ex made a film about “the ups and downs of ‘young love’” based on their former relationship. She confronted her about the film and, when the ex claimed it was more about love in general, she asked for tickets. Her friends are egging her on to attend, but would that be petty? Next, we hear from a 35-year-old woman struggling with the men she’s meeting on the apps. She finds them all so…boring. She asks J&J a series of questions to adjust her approach (i.e. Should she lessen her expectations? Are these incompatibilities a deal breaker?), but they feel like she’s sidestepping an obvious factor in her problem. Learn more about your ad choices. Visit megaphone.fm/adchoices

Something’s comiiinnnnggggg – before we dive into the first email, Jared and Jordana have an announcement (spoiler: it has to do with Fra)! Then, the first email comes from a 32-year-old listener in LA with a common issue. She’s going on dates and they’re fine, but she doesn’t really care to push further. Where’s the lapse in connection, and is it safe to assume it must be coming from her end? J&J start at the crux of her dating issues and, like many of us, it has to do with an old situationship. The Awkward Encounter drove one listener to commit to cutting off her ex for good. Next, we get into our first “Friends to Lovers” submission in a new segment sponsored by Netflix. In anticipation of Bridgerton season 3, listeners are filling us in on how their own “friends to lovers” scenarios played out. The episode ends with a “Red Flag or Deal Breaker?” about voice messages, forgetting a first date, and date-crashing friends. Learn more about your ad choices. Visit megaphone.fm/adchoices

This Sunday Special, we’re taking notes from a professional! J&J are joined by Matthew Hussey (@thematthewhussey), a life coach and best-selling author with nearly 20 years of work elevating lives and relationships. We start with what Matthew came to terms with in the modern dating climate as his career evolved, then J&J get him to delve into how his own love life developed over time and the long-distance relationship that led him to say "I do" last year. His wife Audrey enters the chat to give her POV about their early stages and the surprising text she sent that drove him to make a decision. Plus, he answers listener questions sent in from Instagram, talks about raising your standards, and the importance of communication. Learn more about your ad choices. Visit megaphone.fm/adchoices

Is it petty or prudent to use your life experiences with others in your life’s work? What if you’re one of the biggest pop stars in the world? Before dissecting listener emails, J&J dish first thoughts on Taylor Swift’s new album, “The Tortured Poets Department.” The first email comes from a listener disputing her latest breakup after her ex questioned whether they truly had long-term compatibility. To her, you have to invest in a relationship first in order to build compatibility, so she leaves it up to J&J to chime in and decide. The Awkward Encounter gave us all the ick. Then, the next email is from a listener who can’t decide if she should follow her heart or the advice of her loved ones. She’s seeing a friend of a famous rapper who flies her out and makes her feel special, but her family disapproves and wants her to come down from cloud nine. Is there a chance for something real to blossom with a lifestyle like his? The episode ends with a “Red Flag or Deal Breaker?” about picky eaters, invasive date questions, and threatening to break up after an argument. Learn more about your ad choices. Visit megaphone.fm/adchoices

This Sunday Special is a full debrief as Dulcé Sloan (@dulcesloan) joins J&J in the studio, catching them up on the dating stories she’s telling publicly for the first time, why she doesn’t call romantic interests by their names, and what she’s learned looking back. She takes us back to the time she was seeing “The Mechanic,” breaks down what they had and why it went on for so long, and confronts Jared about what he's looking for. You may know her as a comedian and host of The Daily Show, but Dulcé is also Jared’s friend and ready to be yours too with her new book, “Hello, Friends! – Stories of Dating, Destiny, and Day Jobs”. For more of her dating stories and lessons learned in life, get your copy of Dulcé’s book here: https://amzn.to/44gUGxW Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are back in the studio so nature is healing. Jared talks “peacocking” and shares deets on the commitment he dove into after a weekend in Aspen. Then, Jordana dishes on decision-making with her husband and the tactics that they’re using to get through their home renovations. Next, we receive an email from a male listener who isn’t having much luck making it to date #2. Is there a right way to ask what went wrong? The next email is a listener mid-spiral after her fiancé confessed to a digital affair. Then, the episode ends with a “Red Flag or Deal Breaker?” about a weird house quality, downgraded dinner plans, and lying about age on the apps. Learn more about your ad choices. Visit megaphone.fm/adchoices

Mercury is in retrograde, J&J are out of studio, and existential thoughts are filling the distance between them today. Still reeling from the earthquake and solar eclipse, Jared and Jordana are getting deep into fears, oblivion, and mental health. Then, they dive into an email that doubles as a "Petty or Prudent?" submission. Our listener was dumped by her fiancé after footing most of the bills in preparation of their wedding, but she still has his grandmother's engagement ring. Should she give it back, or is it only fair that she sells it to pay off the debt incurred? She gets into the details of what's transpired since he called the wedding off to let J&J decide where to go from here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Lovers of long intros, buckle up! J&J are jumping in virtually today, so they do a little catch-up from Aspen and Long Island before diving into the episode. Then, our first email is questioning a man's alleged heartbreak. Our listener's friend broke up with a guy, but she's not sure how to take his reaction. Was he really just romantic, or was his reaction the subtle sign of a player? The Awkward Encounter is the accidental sext situation without the ick. The next email comes from a confused listener after her ex reached out wanting to be "all in" only to change his mind 3 days later. J&J discuss WTF happened and how you can avoid situations like this, then they end the episode with a round of "Red Flag or Deal Breaker?" about an odd joke, a last-minute change of plans, and privacy screens. Learn more about your ad choices. Visit megaphone.fm/adchoices

Weddings are on our minds today! After a few listeners sent invitations to their upcoming “I do’s,” J&J thought about the ideal wedding experience if they could attend one. Then, Jordana needs context on “the chair” text exchange from Jared’s Instagram Story coverage of his brother’s wedding. The “Icky or Picky?” is about having sex with someone who shares the same name as a family member. Then, we hear from a listener whose boyfriend’s mom disapproves so much that she emailed a list of her deal breakers. Should his mom’s behavior be a reason to see herself out of this relationship, or can they work through it? J&J discuss the balancing act between a parent and a partner when everyone isn’t aligned. Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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