U Up?

Jared’s 40th birthday is approaching and he might be on the cusp of an impending meltdown. He’s being haunted by images of how he’ll be spending his upcoming 40th: alone, on an international flight to New Zealand (in a Delta One seat, of course). And after purchasing a luxe coffee maker with insane upkeep, Jordana is having some buyer’s remorse. On Icky or Picky, a listener keeps accidentally going on dates with guys with the same last name as her and it’s creeping her out. Later, we hear from a CrossFit betch who is having trouble meeting her match. Her parents say that her impressive physique may be to blame.

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It’s February, which means we can all complain about it officially being the coldest month of the year. To start things off, Jordana tells Jared about her sister’s recent stay at her place and the creative new ways her seven-year-old nephew stress tested her new furniture. Jared’s hot off of a star-studded show at the Comedy Cellar, where Madonna inexplicably performed a 40-minute comedy set. Later we dive into our mailbox, and hear from a listener who worries that all her longterm relationships will end up with a dead bedroom. Also, a recent divorcee finds herself stumbling through her reentry into the dating world and regrettably commissions a pet portrait for a man she was casually seeing whose dog died. In “Awkward Encounter,” Jared & Jordana advise a listener who just realized she went on dates with two guys who are close friends and debates whether or not she should tell them. In “Red Flag or Deal Breaker?“, we hear about a guy who pretends he went to an Ivy League school, an ex-boyfriend who might be a little too obsessed with his sister and a woman who won’t stop comparing the man she’s seeing to her ex.

Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903. 

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Another Bachelor breakup broke the internet this week. After four years of dating and no engagement in sight, Matt James called quits on his relationship with Rachael Kirkconnell. With all the confusion and discourse over this breakup, Jared and Jordana enter the chat with their own takeaways. On “Icky or Picky,” a listener ends up dating a meme king which is all fun and games until he sends her about 30 memes over the course of two days. When things don’t work out between them, he sends her a Venmo request for the cost a previous date. In a dramatic reading of these text exchanges, Jared channels his inner spaghetti Western villain. Later, we hear from a listener who’s experimenting in her love life by dating a “nice guy” for once, who just so happens to do everything with his ex girlfriend. And by everything, we mean couples massages, hanging out multiple times a week and going on romantic vacations.

Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903. 

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We’re one month into 2025 and J&J are here to keep you motivated, even if you already quit your New Year’s Resolutions. Jordana is fresh off of hosting a housewarming party and Jared is struggling to find time to write a book about dating while actively still dating. Later, we hop into emails, including a listener who wonders if her friends actually need to know the guy she’s dating and we answer the mother of all dating questions: How do I approach the gym hottie without being creepy? Today’s “Awkward Encounter” takes us to church with a wild listener story about hooking up with their former worship leader. On “Red Flag or Deal Breaker,” J&J debate if terrible reviews on RateMyProfessor are a good reason to not date someone, consider what proper texting etiquette looks like during a national emergency, and question whether it’s bad form to refuse to go to a certain dating spot because it isn’t romantic enough.

Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903. 

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More than 25 years later, "Sex and the City" is still on our minds when it comes to how we would handle dating and relationships. However, since Gen Z has entered the chat and millennials hit double-digit rounds of rewatching, the discussions have shifted from identifying as the Carrie of your group to Carrie Bradshaw arguably being one of the worst characters we know. Still, Jared and Jordana aren't ready to hop on the hate train yet. They break down why we're so repulsed by some of Carrie's most memorable moments and how it translates into our evolving love lives. Plus, they play a round of "Icky or Picky?" about a flirty text that fell flat. The episode ends with an advice email about overcoming post-breakup pettiness. Is it natural to want to wish pain upon your ex when you're still reeling from a breakup, or do specific actions need to be taken to move on?

Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903. 

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It’s the dead of winter and we’re all in “hamper girl mode.” Jordana and Jared shake off the cold by jumping into some heated dating questions. Can a person have too many ongoing chats on a dating app? How do I know if breaking up was the right decision? And TikTok has spoken: Ghosting is out and “avoidant discarding” is in. J&J discuss this new dating term and how it’s even worse than just leaving someone on read. Later, a listener meets his Reese Witherspoon-esque dream girl. The catch? She lives in a completely different city. J&J give him pointers on how to set up a second date without scaring her off. The “Awkward Encounter”, a typically smooth bartender dreads a looming speed dating event he signed up for. J&J coach him on how to make a great first impression. Then we play “Red Flag, Deal Breaker?,” about a post-sex breakup comment, missing ice cube trays and a date who is only looking for one thing.

Have a dating question for Jordana and Jared? Send an email or voice memo to [email protected] or leave us a voicemail at our dating hotline 212-589-8903.

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It’s a second-guessing time of year on the podcast and in the dating world! Should you go out even though you're not feeling it in the thick of winter? Should you go for it with the cute person you met in your hometown? All the kinds of questions that J&J are tackling this Friday! They play a round of “Petty or Prudent?” about texting an ex’s family that his cheating is the reason your relationship is ending. Plus, a listener writes in about wanting to pursue the guy in her hometown thousands of miles away, but she’s not sure she’s in it for the right reasons. After her last breakup and a similar situation, is going for a Hallmark-level romance just a way to evade vulnerability or a better way to ease into a new relationship? J&J discuss her circumstance and whether she’s processed emotions enough to make a decision.

Have a dating question for Jared & Jordana? Send an email or voice memo to [email protected] or leave us a voicemail at our hotline 212-589-8903

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In the midst of reflecting and changing, this episode is on theme for the new year shifts you’re trying to make happen! After J&J catch each other up on their holiday breaks, a listener committed to keeping casual wonders how she can keep her anxious dating habits at bay. The Awkward Encounter would be a nightmare for any parent and teen. Then, after dedicating his 20s to his career, a 30m listener asks how to make his focus more dating-centric. Can a demanding job complement his dating life or is it time for a career change? The episode ends with a “Red Flag or Deal Breaker?” about strange Instagram follows, working throughout a date, and a quirky reuse choice.

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If someone isn’t for you, let them. Easier said than done, but in today’s episode, we’re joined by Mel Robbins (@melrobbins), motivational speaker and author of “The Let Them Theory”, to tell us how. After Mel comes in hot with a reality check that we may be the cause of our biggest problems, Jared and Jordana question how listeners can apply the Let Them Theory to their lives whether they’re on the apps, ready to have kids or in a constant communication rut with their significant other.For more from our guest, pick up your copy of “The Let Them Theory” here: https://amzn.to/3DJDmsr

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This week, J & J are fresh off a dinner party together, but Jared’s own awkward encounter at a bar afterwards has him regretting that nightcap martini. After some daydreaming about winter getaways, we dig into the e-mails, starting with a listener who put their friend onto the pod, watched them succeed at finding love, but keeps striking out on their own. They tackle a couple of listener’s dating app woes, like should you stop replying if they make an edit to their profile you really dislike? Today’s "Awkward Encounter" pushes the boundaries between “awkward” and “heartbreaking,” with a write-in from a woman who thought she was getting a ring but got a break-up instead. Keeping the New Year unhinged, “Red Flag or Deal Breaker” covers disclosing food allergies, being pushy about “going to my place”, and talking about your parents sex lives on a first date… which we think might require a little more professional help.

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