On this week’s episode, J&J start with a chat about the start of fall (aka hookup season), Jordana’s birthday plans, and her gift to all of you. The first emailer asks if she should go out with a guy who previously canceled their first date because he decided to be exclusive with someone else. Should she still go out with him if she feels like his second choice? The Awkward Sexual Encounter is a one night stand gone wrong. Later, a U Up? Hotline caller asks how to handle birthday gifts in a new ...
Sep 07, 2022•2 hr 30 min•Ep 377•Transcript available on Metacast J&J are back with another Sunday Special, and this week the emailer asks why she keeps falling for her long distance coworkers. She explains that she quickly hit it off with a coworker she only knew via Zoom, but he ended things after she visited him in his city to meet IRL. Now, she feels herself falling into the same pattern with a different coworker. Should she go for it? Is there a deeper reason she’s in this situation all over again? Jared and Jordana break down where she’s being too hard o...
Sep 04, 2022•30 min•Ep 376•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a recap of Jordana’s trip to Charleston and Jared’s side hustle as a bachelorette party planner. Then, they talk about an article that exactly 3 people sent to Jordana called “The Rise of Lonely, Single Men.” The Awkward Sexual Encounter is a barnyard bang. Later, a listener asks if her f*ck buddy of 5 years could possibly turn into a real relationship. Why does she suddenly want something more with this person? J&J finish the episode with...
Aug 31, 2022•2 hr 32 min•Ep 375•Transcript available on Metacast J&J are back with another Sunday Special, and this week they start out by planning Jordana’s trip to Charleston. The emailer asks Jared and Jordana how much she should believe drunk texts from a guy saying how much he likes her. Are drunk texts sober thoughts? Does it matter that he’s followed new girls on Instagram since they met? They finish the episode with a listener-submitted jingle to the tune of the Full House theme song. Learn more about your ad choices. Visit megaphone.fm/adchoices
Aug 28, 2022•35 min•Ep 374•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a conversation about a recent date Jared went on where he might be the red flag. The first emailer asks J&J’s opinions on “Are We Dating The Same Guy?” Facebook pages popping up in many cities. Are these groups empowering for women or a slippery slope? The Awkward Sexual Encounter is less than eye-deal. Later, a listener writes in about her fiancé’s underwhelming proposal. How can she ask him to make up for it without seeming like she’s not ex...
Aug 24, 2022•1 hr 25 min•Ep 373•Transcript available on Metacast Jared and Jordana are back with another Sunday Special, and this week they start out with a discussion about Jordana’s dorm mistakes and the vulnerability of being a little clueless. The emailer sends in screenshots of a text exchange where a guy vetted her by asking about deal breakers before the first date. If someone gives an extensive list of deal breakers before a first date, is it even worth it to go? J&J discuss what you actually need to know about someone and how much texting is too much...
Aug 21, 2022•40 min•Ep 372•Transcript available on Metacast On this week’s episode, Jared is back from his French adventure and ready to give Jordana the full recap of the trip and responses to his social media coverage. The first emailer asks J&J’s opinions on a “Singles List” she encountered at a recent wedding. Is it a fun way to meet people or is it a little presumptuous of the bride and groom? The listener forgets her underwear in the Awkward Sexual Encounter. The next email asks how to deal with snoring in a relationship. Are the listener and her b...
Aug 17, 2022•2 hr 35 min•Ep 371•Transcript available on Metacast J&J are back with another Sunday Special, and this week, they’ve got the screenshots from a listener who’s confused by the lack of communication from a guy she’s dating. He told their mutual friends that he’s into it, so why won’t he initiate any texts even after she brought it up? Is she confused about whether or not he likes her or does she just not like him? J&J translate the texts to what the emailer and this guy would say if they were both being completely honest. Plus, they talk about how ...
Aug 14, 2022•44 min•Ep 370•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a discussion about how every family has a “lazy one” and why they need a travel agent. The first emailer asks how to trust your gut on whether or not you like someone. She lists several reasons she doesn’t think they’re a match, but is she being too judgmental? The Awkward Sexual Encounter involves an unusual accessory. Later, a listener asks if she should be concerned that her boyfriend never had a “hoe phase.” Do men even think about dating ...
Aug 10, 2022•1 hr 27 min•Ep 369•Transcript available on Metacast J&J are fresh off the flight from the U Up? Live show in Chicago and ready to solve dating with another Sunday Special. The listener writes in about a situationship with (debatably) 22 years of history. She explains that they didn’t want to date long distance, but now that they’re finally going to be living in the same city, she’s not sure what to expect. Should she be worried that things will move too quickly since they’ve known each other for so long? Plus, J&J talk about how they might not kn...
Aug 08, 2022•36 min•Ep 368•Transcript available on Metacast Jared and Jordana start this week’s episode with a French lesson for Jared and a discussion about “going out woman” vs. “going home woman.” The first emailer asks how often she should be initiating text conversations with guys she’s dating. Is 60% of the time too much or is she just overthinking all of this? The Awkward Sexual Encounter is almost sacrilegious. Later, a hotline caller asks how to non-awkwardly break out the lube during sex with a new partner. Do guys care about this? They finish ...
Aug 03, 2022•1 hr 5 min•Ep 367•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are joined by Patti Stanger (AKA the Millionaire Matchmaker). They start out with a conversation about what has changed about dating over the course of Patti’s career and being “dickmatized.” Later, they answer an email from a listener who’s having a hard time being attracted to her boyfriend because of his height. Should she try to overcome her own insecurity of feeling “huge” next to him? Or is feeling this way a deal breaker? Jared, Jordana, an...
Jul 31, 2022•50 min•Ep 366•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a conversation about Jared’s TedTalk (which we *think* is available now) and how going on vacation can turn you into a monster. The first emailer writes in to ask how to deal with her fiancé continuing to follow women from before their relationship. She says she trusts him, so is her “ick” valid? How much can she negotiate his following count? The Awkward Sexual Encounter involves an unfortunate bathroom break. Later, a listener emails in abou...
Jul 27, 2022•1 hr 16 min•Ep 365•Transcript available on Metacast J&J are back with another Sunday Special, and this week they’re answering an email from a listener who’s been playing DM tag with the same guy for 5 years. Now they’re finally living in the same place, but they’ve only managed to get together twice, both with no kiss. Did they miss their dating window? Or is he just more interested in making friends in his new city? Plus, they discuss the person you go on one date a year with because you don’t trust your former self. J&J finish the episode with ...
Jul 24, 2022•29 min•Ep 364•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a reveal of the destination for Jared’s upcoming solo vacay. The first emailer asks about the difference between cute and hot. Is she wrong for being annoyed that she gets called cute on the dating apps as a 34-year-old woman? Jared explains the difference between various physical compliments from a guy’s perspective. The Awkward Sexual Encounter involves a missing press-on nail. Later, a listener asks how to stop obsessing over an engagement ...
Jul 20, 2022•1 hr 12 min•Ep 363•Transcript available on Metacast Jared and Jordana are back with another Sunday Special, and this week they start with a midsummer pep talk for all the singles. This week’s emailer writes in about a trend of guys claiming they were intimidated by her on the first date. Is she coming off too confident for these guys' egos? Or does it have something to do with her sexuality? Plus, they discuss how men actually behave when they’re intimidated. J&J finish the episode with a listener-submitted jingle all the way from Hawaii. Learn m...
Jul 17, 2022•38 min•Ep 362•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a recap of their 4th of July weekends, including Jared’s thoughts on being the single guy of his friend group and his mom’s reaction to an upcoming solo trip. Then, Jared reads some of his recent Hinge interactions, and they discuss the spectrum of cheesy to jaded daters in New York. The first emailer asks when she should tell guys she’s dating about a random friend makeout after finding out that her friend tells women about it on the thir...
Jul 13, 2022•2 hr 34 min•Ep 361•Transcript available on Metacast J&J are back with another Sunday Special, and this week they start with a discussion about couples' trips at different stages of a relationship. This week’s emailer writes in for help deciding if she should move forward in her relationship even if her boyfriend isn’t as passionate as she would like. Is she just seeking the drama she had with her exes? How can she get an answer out of him about their future plans? Plus, J&J listen to a listener-submitted jingle to finish the episode. Learn more a...
Jul 10, 2022•38 min•Ep 360•Transcript available on Metacast On this week’s episode, Jared and Jordana are back in the studio talking about the art of eye foreplay and meeting new people when you go out alone. The first emailer asks about the infamous Hot/Crazy scale created by Barney on “How I Met Your Mother.” Are men really attracted to “crazy” women? And does the graph work if the genders are flipped? The Awkward Sexual Encounter includes a surprise visit from a landlord. The next email is from a listener wondering if she’s the assh*le for being turne...
Jul 06, 2022•1 hr 23 min•Ep 359•Transcript available on Metacast J&J are back with another Sunday Special just in time to solve all your 4th of July dating worries, and this week they start out with a chat about single vs relationship holidays. The emailer writes in about a guy she’s been seeing casually for a few months. When she tried to address their slow momentum and mixed signals, he explained that he saw her more as a friend and he’d like to keep it that way. Should you “stay friends” with someone you only know in a romantic context? J&J give her some t...
Jul 03, 2022•29 min•Ep 358•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a recap of our Boston show and a discussion about what counts as a “failure” in dating. Jared reads some texts and Jordana does a Deal Reveal to decide if he’s being too judgmental over TSA preferences. The first emailer asks what a low-cost first date means. Is he not into you if he just asks you out for coffee or a walk? Or is inflation just hitting everyone hard right now? The Awkward Sexual Encounter is another tale of missing panties....
Jun 29, 2022•1 hr 11 min•Ep 357•Transcript available on Metacast J&J are back with another Sunday Special, and this week the emailer asks if she’s being too chill in dating. They start out with a conversation about how “chill” is perceived by men and women and what the right level of chill is. The listener submits screenshots where a guy she went on one date with slides into her DMs to ask her out again, explaining that he didn’t think she was interested initially. Is she playing things too cool and not showing enough interest? Or is he just saying what she w...
Jun 26, 2022•28 min•Ep 356•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a follow up discussion about why a guy might not want to date someone with a TikTok following and an update on Jared’s feelings about being single. The first emailer writes in about how she and her boyfriend are doing great except for one thing: he’s never said “I love you.” Do actions really speak louder than words? Is it a bad idea to get engaged without him saying those 3 words first? The Awkward Sexual Encounter feels like an episode of Be...
Jun 22, 2022•1 hr 19 min•Ep 355•Transcript available on Metacast It’s Faux Pas Sunday on the pod, and Jared and Jordana are starting out with a U Up-Date from the infamous Poof from our episode on 5/22. The emailer writes in asking how to deal with guys who quickly set the expectation that they’re just looking for a hookup. How much should she go with the flow? Is she too worried about wasting her time? Plus, they give the listener some mirror mantras to repeat for her next date. Learn more about your ad choices. Visit megaphone.fm/adchoices
Jun 19, 2022•44 min•Ep 354•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a talk about the official vocal coach of the U Up? Podcast, a proposal at one of Jared’s recent shows, and why you should listen to the pod with your S.O. The first email comes from a male listener who isn’t sure if the girl he’s dating is attracted to him because they’ve been on many dates, but they haven’t gotten physical yet. What happens if they aren’t sexually compatible after all this lead up? The Awkward Sexual Encounter is a real eye-o...
Jun 15, 2022•2 hr 30 min•Ep 353•Transcript available on Metacast J&J are back with another Sunday Special, and this week they start things off with a conversation about Flo-Rida and all things Australia. The email is a deal reveal from a guy who tried to get vulnerable after feeling a shift in the relationship with a girl he’s been seeing for a couple of months. Did he blow it by bringing it up or was the relationship already doomed? Plus, they talk about how important someone’s response to vulnerability is. Learn more about your ad choices. Visit megaphone.f...
Jun 12, 2022•35 min•Ep 352•Transcript available on Metacast On this week’s episode, Jared and Jordana start with a conversation about post-MDW energy in New York and bad bar behavior. The first emailer asks whether chemistry or connection is more important in dating. How much can you really tell from a first kiss? The Awkward Sexual Encounter is a warning for any laser hair removal enthusiasts. Later, a listener writes in about her boyfriend’s unenthusiastic reaction to her new work opportunities. Does he really want a partner who’s home all the time or ...
Jun 08, 2022•1 hr 29 min•Ep 351•Transcript available on Metacast Jordana and Jared are back with another Sunday Special, and this week they start out with a listener jingle and a conversation about the impact of American Idol. The emailer submits screenshots from a guy she’s been on one date a year with since 2020. Should she believe him when he says they’re on the same page now after he ignored her initial reveal? J&J give their takes on what she could have done differently and how social media plays a role here. Plus, they discuss birthday dinners and hook ...
Jun 05, 2022•36 min•Ep 350•Transcript available on Metacast On this week’s episode, Jared and Jordana start out with a recap of Jared’s time at a chili cookoff and the correct pronunciation of Nevada. The first emailer writes in after a guy she went on five dates with seemed spooked after she pointed out that it was, in fact, their fifth date. Are fifth dates really that big of a deal? The Awkward Sexual Encounter involves a missing pair of underwear. Later, a listener asks if she should give her boyfriend a vacation hall pass. Will they regret not havin...
Jun 01, 2022•1 hr 18 min•Ep 349•Transcript available on Metacast On this week’s Sunday Special, Jared and Jordana are shedding light on some cringey post-breakup behavior. A listener writes in about how her ex-boyfriend broke up with her and then came back into her life with a bottle of expensive shampoo. Now they’re broken up again, and she received a note from him addressed to her dog along with a box of dog toys. Jared reads the note in his best dog owner voice, and they try to understand what his goal is here. Plus, they discuss the right way to get back ...
May 29, 2022•29 min•Ep 348•Transcript available on Metacast 
