Jared and Jordana are reunited in the studio for this week’s episode, and they start out with a recap of Jordana’s honeymoon and a few luxury lounge complaints. Then, Jared fills Jordana in on everything that’s been happening in his dating life, including redownloading the apps and getting tired of them again all in a 3 week span. Later, J&J play a round of Red Flag or Deal Breaker about grocery shopping, self-help books, and unconventional pajamas. Plus, they listen to some of the jingles submi...
Apr 06, 2022•1 hr 34 min•Ep. 333
On this week’s Sunday Special, the emailer asks Jared and Jordana to help her understand what’s happening with her “best guy friend” who said he wanted to try dating her but kept canceling their dates. Is there any truth to their romance or is she just prematurely writing the “Our Story” page? J&J give her a reality check and discuss whether or not men and women can actually be friends if they’re attracted to each other. They finish the episode with a round of J&J’s Final Say about headphone eti...
Apr 03, 2022•35 min•Ep. 332
On this week’s episode, Jared and Jordana start with an email from a listener who doesn’t know how to tell her boyfriend that she used to hook up with her coworker. Does he really need to know or is ignorance bliss? The Awkward Sexual Encounter involves canine voyeurism. Later, a U Up? Hotline caller asks why she can’t seem to get past the 3-monther. Finally, J&J wrap up the episode with a round of Red Flag or Deal Breaker about Plan B, abs, and potentially armed robbery. Learn more about your a...
Mar 30, 2022•1 hr 3 min•Ep. 331
Jared and Jordana are back with another Sunday Special episode, and this week they answer an email from a listener who wants to know if we’ve created a whole other monster by shaming f*ckboys. She tells a story about how a guy she’d only been going out with for a few weeks asked her on a date to break it off. Did he really think this was better than just sending a text? They finish the episode with a round of J&J’s Final Say about mediocre dating app prompts and dating outside your city. Learn m...
Mar 27, 2022•32 min•Ep. 330
On this week’s episode, Jared and Jordana start out with a discussion about Jordana’s honeymoon plans and their favorite jingles. The first emailer wants to know what the “bare minimum” actually is, and J&J craft an elaborate metaphor comparing dating to apartment hunting. The Awkward Sexual Encounter is a stinker. Later, an emailer asks how she should handle her boyfriend delaying the engagement ring shopping appointment. Is it still romantic if she has to bug him about it? Jared and Jordana fi...
Mar 23, 2022•1 hr 17 min•Ep. 329
J&J are back with another Sunday Special, and this week they’re talking about how to date seriously when you travel for work. The emailer submitted screenshots with a guy she was seeing while living in his city for 13 weeks, and it’s pretty clear he’s not interested in extending her stay. How should she bring up her work situation to avoid guys who only see her as a short term hook up? Plus, Jared shares his experiences dating when traveling all the time. Finally, they play a round of J&J’s Fina...
Mar 20, 2022•36 min•Ep. 328
Jared and Jordana start this week’s episode with a story about how Jared accidentally ended up on a 2-on-1 date. The first emailer asks if she should break up with her boyfriend or Instagram after a fight over him not posting her to his account. Would his response have been better if she expressed her concerns differently? The Awkward Sexual Encounter is a goose-fueled romcom. Later, a hotline caller asks why women always want to change men. Is he going to have to give up his video games no matt...
Mar 16, 2022•1 hr 20 min•Ep. 327
On this week’s Sunday Special, Jared and Jordana are joined by comedian Taylor Tomlinson to solve dating and chat about her new Netflix special. They start out with a discussion about Taylor’s dating life, mental health journeys, and hate mail. Later, they answer a listener's email about men’s lack of planning skills. Can he really not make a plan or does he just not want to? Plus they discuss whether or not “if he wanted to, he would” is an empowering point of view. Learn more about your ad cho...
Mar 13, 2022•49 min•Ep. 326
On this week’s episode, Jared and Jordana start out with a recap of Jordana’s friend’s wedding and a discussion about how men and women look at life stages differently. The first emailer asks if she’s wrong to be turned off by her matches asking for a FaceTime or phone call before the first date. Is this the new normal? The Awkward Sexual Encounter involves some unwanted help from the caller’s mom. Later, a listener asks how to go from first dates to dating. Can you really progress a relationshi...
Mar 09, 2022•1 hr 25 min•Ep. 325
On this week’s Sunday Special, J&J are breaking down the texts between a listener and a guy she went on a date with while visiting a friend in the city where she plans to move. After a couple weeks of non-stop texting, he sent a text saying he didn’t want to keep talking until she moved. Is it really about timing or was he just not feeling it? They finish the episode with a round of J&J’s Final Say about serial killer jokes and texting chemistry. Send your questions and messages to the podcast b...
Mar 06, 2022•35 min•Ep. 324
Jared and Jordana are back with another episode, and this week they start out with a discussion about Jared’s birthday reflections and why he doesn’t want to “do drinks” anymore. The first emailer asks how she should tell her boyfriend about her nose job. Will it impact how he sees her? Next, J&J are closing the sexting gap with some help from the sext-y nurse from our February 16th episode. Later, a guy writes in asking how to stop feeling threatened by his girlfriend’s exes. They finish the ep...
Mar 02, 2022•1 hr 23 min•Ep. 323
Jared and Jordana are back with another Deal Reveal on this week’s Sunday Special. The emailer writes in about a guy she almost overlooked on the apps because of his “weird” profile, but she was pleasantly surprised by how much she liked him. After their 5th date she suggested he follow her on Instagram since she would be leaving town, but he declined. Is this a red flag? Is he self-conscious about his own profile? Plus, they discuss how she should address it. They finish the episode with a Brea...
Feb 27, 2022•37 min•Ep. 322
On this week’s episode, Jared and Jordana start out by discussing Jared’s plan for the worst day of the year (AKA his birthday) and his recent foray into van life. Then they discuss the Netflix documentary “The Tinder Swindler” about a man who fooled his Tinder dates into giving him thousands of dollars and what these extreme circumstances can teach the average dater. The Awkward Sexual Encounter involves a nosey little brother. Later, a listener asks how to stop being a “cool girl.” They finish...
Feb 23, 2022•1 hr 39 min•Ep. 321
Jared and Jordana are back with another Fuckboy or Nah? on this week’s Sunday Special. The emailer writes in about a guy she met before the holidays. He acted very “coupley,” but a few weeks later, he bailed on their plans and her friend saw him on a date with another woman. Jared and Jordana weigh in on which of his actions actually mean something and give her advice on how to deal with the “we should” kind of guy. Finally, they play a round of J&J’s Final Say about how much you owe someone aft...
Feb 20, 2022•37 min•Ep. 320
On this week’s episode, Jared and Jordana are talking all about how to keep dating fun in the winter. The first emailer asks if it’s worth it to date now or if she should just wait until spring, and J&J give her some tips to spice up her swiping routine. The Awkward Sexual Encounter involves a very sexy nurse. Later, a listener asks how to tell her boyfriend that she’s not comfortable with him using her phone all the time. Is she right about it being an invasion of privacy? Finally, they finish ...
Feb 16, 2022•1 hr 6 min•Ep. 319
Jared and Jordana are back with another Sunday Special, and this week, they start with Jared’s love letter to Tom Brady. Then, they break down the texts between a listener and her guy friend. They went on a date, but both agreed they were better off as friends. So why is he now calling her a GILF (grandma I’d like to f*ck)? J&J discuss his motivations and how she should move forward. Learn more about your ad choices. Visit megaphone.fm/adchoices
Feb 13, 2022•35 min•Ep. 318
Jared and Jordana are back with another Lightning Round episode, and this time it’s all about Valentine’s Day. They answer 10 questions submitted by our Instagram followers and break down exactly what you should do for Valentine’s Day whether you’re single, in a relationship, or somewhere in between. They walk us through whether or not you should try to “Define the Valentine” around February 14th, and how to go about it if you do. Plus, they discuss why you should lean into the clichés of the ho...
Feb 09, 2022•1 hr 10 min•Ep. 317
On this week’s Sunday Special, Jared and Jordana are talking all about the first season of And Just Like That. They start out by discussing the glossy legacy of the original Sex and the City and how the creators betrayed its true fans. Where were all the brunch table dating breakdowns? Then, they talk about Carrie and Big’s relationship and how the message was bad for its young, single viewers. Plus, they give their opinions on each and every character. Learn more about your ad choices. Visit me...
Feb 06, 2022•1 hr 2 min•Ep. 316
On this week’s episode, Jared and Jordana start out with a discussion about Jordana’s entry to TikTok and how it differs from Instagram. Then they chat about a long-awaited first date that Jordana set Jared up on. The first emailer asks if the classic Sex And The City quote comparing men to cabs is accurate. Do men actually end up with the first woman that comes along when they decide they’re ready? The Awkward Sexual Encounter is a game of musical bunkbeds. The next emailer writes in about how ...
Feb 02, 2022•1 hr 38 min•Ep. 315
Jared and Jordana are back with another Sunday Special, and this week they’re talking about Jared’s favorite sandwich in LA and how to date someone with a heavy personal life. The emailer writes in about a guy she really likes except that he routinely takes over a week to respond to her texts. When she called him out on it, he revealed that his mom is dying and that’s why his communication has been slow. Can she pursue this relationship without compromising on what she wants? Later, they play a ...
Jan 30, 2022•28 min•Ep. 314
On this week’s episode, Jared and Jordana start out with a discussion of how Jordana’s husband feels about her most recent U Up? With Benefits episode. Then, they talk about a full-blown presentation someone DM’d Jared to try to set him up with her friend. Should PowerPoints be a requirement for a fix up? J&J go over each slide to tell you exactly how to make a presentation for your own friends. The Awkward Sexual Encounter involves a visit from a raccoon. Later, a listener asks how she should d...
Jan 26, 2022•1 hr 30 min•Ep. 313
Jared and Jordana are back with an emergency Sunday Special all about West Elm Caleb, a New York guy who’s blowing up on TikTok for ghosting, love bombing, and sending unsolicited dick pics. Maddy gives the timeline of how this all started, and Jared and Jordana discuss the extent of his offenses. Does he really deserve all of this public shaming? Plus, they talk about how the power dynamics on dating apps play into these issues. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jan 23, 2022•48 min•Ep. 312
On this week’s episode, Jared and Jordana start out with a discussion about the most annoying person on vacation and Jared’s conflicted feelings about dating apps. The first emailer asks how to navigate the early stages of dating a sober person. Should she address it before planning the first date? The Awkward Sexual Encounter was thwarted by a full moon. Later, a listener asks how to deal with their partner being a workaholic. Is there room for compromise or are they just not the match? J&J fin...
Jan 19, 2022•1 hr 34 min•Ep. 311
On this week’s Sunday Special, Jared and Jordana answer an email from a listener asking if her situationship fizzled because of an awkward sexual encounter. They went on four good dates, but when they finally had sex, it was a letdown. He started being distant afterwards, so she texted him to ask what was up. J&J break down the texts to try to figure out what happened here. Was it really about the sex? And does it really matter either way? Finally, they play a round of J&J’s Final Say about dati...
Jan 16, 2022•34 min•Ep. 310
On this week’s episode, Jared and Jordana start out with a discussion about how we’re all living in an episode of Curb Your Enthusiasm and what it takes to really be excited for a first date. The first emailer asks if she’s crazy for wanting to marry her first serious boyfriend. Is FOMO from her single friends a sign that she needs to date around more? The Awkward Sexual Encounter involves a very needy puppy. Later, an emailer asks how to make it clear to her guy friends that she’s not romantica...
Jan 12, 2022•1 hr 22 min•Ep. 309
J&J are back with another Sunday Special, and this week they’re breaking down the texts between a listener and a guy she’s seeing casually. They talked about making plans for the weekend, but he wasn’t sure of his schedule and said he would let her know. When she didn’t hear from him she assumed he just wasn’t interested, but when he reached out later, she gave him a piece of her mind. Is she wrong for expecting him to follow up on plans even though they were keeping it casual? Plus, they discus...
Jan 09, 2022•27 min•Ep. 308
On this week’s episode, Jared and Jordana start out with a discussion about their New Year’s resolutions. Then, they answer an email regarding a TikTok that lists questions you should ask on a first date to avoid wasting time. Do those questions actually help you get to know someone? Is anything really a waste of time in dating? The Awkward Sexual Encounter involves a chicken suit. Later, an emailer writes in about setting boundaries with her boyfriend’s ex. Is an ex ever calling just to “catch ...
Jan 05, 2022•1 hr 1 min•Ep. 307
Jared and Jordana are back with another Sunday Special, and this week they’re talking all about money and dating. First, they answer an email from a listener who makes ten times more than her boyfriend. Should she decline his offers to pay for dates? Then, Jared and Jordana are joined by Kurt and Steven, the stars of Joe Millionaire: For Richer or Poorer, to discuss the new show and how much money matters when it comes to love. Finally, they debate some unpopular opinions about jobs, money, and ...
Jan 02, 2022•44 min•Ep. 306
On this week’s episode, Jared and Jordana start out by reflecting on this year of the pod. The first emailer asks if she’s being too picky or not picky enough when it comes to dating. Should she swipe right on fewer people or give those matches more time to develop a connection? The Awkward Sexual Encounter involves a missing condom. Later, a listener asks if guys like her less because she offers to pay for dates. Is it a turn off to men? Finally, J&J play a round of Red Flag or Deal Breaker abo...
Dec 29, 2021•1 hr 8 min•Ep. 305
Jared and Jordana are back with another Sunday Special, and this week they start out with a discussion about being single around the holidays. Then, they dissect the breakup texts between a listener and a woman he went on two dates with. Why would she keep flirting with him after saying she doesn’t want to go out again? Plus, they discuss why she says he’s too sweet for her. Learn more about your ad choices. Visit megaphone.fm/adchoices
Dec 26, 2021•28 min•Ep. 304
