Lordy, Lordy look who’s 40! It’s the “Worst Day of the Year” aka Jared’s birthday. Now that he’s over the hill, Jared is embracing his “I want to speak to the manager” energy and reflecting with Jordana on the peaks and valleys from the past year.

Then, we play Petty or Prudent and hear from a listener who got dumped the day after her boyfriend planned a romantic dinner for their one-year anniversary. Later, we dive into an email about a woman who tries to backpedal into dating a guy she once ended things with when he gave her the ick.

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Jared’s fresh off of a trip to Montreal, or as he calls it The Coldest Place on Earth, and comes back with hot takes about the food and one glowing restaurant recommendation. Then J&J gab about their recent trip to L.A. and the difference in hotness factor between Los Angeles and New York (Gremlin Swamp People unite!). They also reflect on a strange interaction they had with a recently divorced man at a bar.Later, we dive into emails and hear from a listener who feels that her boyfriend made a joke at her expense that went too far. On an Awkward Encounter that we’ll never forget, a listener takes a chance going to a playoff hockey game with a guy she just met. Things take a turn when the “Mayor of Detroit” picks her up in a Dukes of Hazard themed golf cart and gets plastered at the game. Then a listener taps J&J for advice on a romantic connection where the physical isn’t matching the emotional one. We end with a round Red Flag Deal Breaker about a forgotten vasectomy, a mean quote from a Rate My Professor review, and an aspiring “boy dad.”

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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This bonus episode is sponsored by Netflix! J and J are reflecting on five years of "Love is Blind" and they’re doing it in the most authentic way possible-in the pods! They find out the hard way what it's really like to communicate in the pods as they test themselves on their emotional intuition. Then, they go on to share their two cents on the communication styles of some of the most iconic couples while breaking down the impact the show has had on modern relationships. Plus, Jared and Jordana go in for a round of Couples Court as they ponder why we don’t walk away when a partner gives us the shrug? They round out the episode with an epic Love Is Blind version of Red Flag or Deal Breaker, pod edition.

Don’t miss Season 8, streaming now only on Netflix – new episodes drop this Friday!

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Jared “Cupid” Freid and Jordana “Matchmaker” Abraham are here to answer all your Valentine’s Day questions. This year for V-Day, Jared’s off to Alpharetta, Georgia for a block of shows and Jordana’s staying in while hubby Mike cooks her up something special. J&J discuss what the perfect meal for V-Day is that still leaves room for romance (for our home cooks, Chef Jared suggests grilled chicken, penne and spaghetti squash). Then in partnership with Shake Shack, we play a special game called BOGO or NOGO where J&J evaluate situationships and decide if listeners should enjoy the Shake Shack’s Smoke Shack BOGO deal with them or save it for someone more deserving. Later, we dive into a lightning round of V-day questions like, “when is it too soon to celebrate Valentine’s Day with someone you’re dating?”, “how do I tell my partner I want to do something for V-day?” and “how do I ask the guy I’m casually seeing if we’ll be spending Valentine’s Day together?” 

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Jordana’s gone full-on suburbs. She’s enrolled in a “tennis clinic” and in between perfecting her serve is trying to infiltrate the neighborhood gossip circle. She continues to debate the pros and cons of pulling the trigger on getting a dog. Later, J&J give a pep talk to a listener who recently went through a bad breakup after realizing that she and her longterm partner were not on the same page regarding kids. On Awkward Encounter, things get messy after a dog steals a listener’s menstrual cup. And this week’s Red Flag or Deal Breaker? has Jared and Jordana wondering if bad hygiene is a valid reason to dump someone.

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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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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