Jared and Jordana are back with the first episode of November. They start with a discussion about Jared and Jordana’s favorite holidays and break down what it means when people say they’re “so single.” The first emailer asks if a guy not asking any questions about her is a reason to end the relationship. J&J rephrase her email to help her see this situation clearly. The Awkward Sexual Encounter involves some improper condom disposal. Later, a listener asks why old situationships pop back up once...
Nov 02, 2022•1 hr 23 min•Ep. 393
J&J are are joined by special guest Delaney Rowe for a spooky Halloween Special. They start with some horror stories about UTIs, DM slides, and the meanest comments they’ve gotten online. Then they dive into Delaney’s dating life and how her career has impacted it. In the spirit of spooky season, they answer an email asking whether or not it’s ghosting if both people stop texting. Is “ghosting” overused in general now? Plus, Delaney asks Jared why men make promises they don’t intend to keep. Lea...
Oct 30, 2022•53 min•Ep. 392
On this week’s episode, J&J start by launching Jared’s presidential campaign to fix Halloween scheduling and giving some Halloween dating tips. The first emailer asks if “He’s Just Not That Into You” holds up in 2022. If the guy she hung out with once wanted to see her again, wouldn’t he just make a plan? What do people actually mean when they say “if he wanted to he would”? The Awkward Sexual Encounter is a cautionary tale for sports bar hookups. Later, a listener asks how to recover from the f...
Oct 26, 2022•1 hr 28 min•Ep. 391
J&J are back with another Sunday Special, and this week they’re joined by Ramit Sethi, author of “I Will Teach You To Be Rich.” They start with a conversation about Ramit’s work with couples to change their mindsets on money, and he gives an exercise for couples to open up the conversation about their finances. Later, they answer an email from a listener wrestling with an income difference in her relationship. She’s moving in with her boyfriend who makes $300k more than her, and she can already ...
Oct 23, 2022•1 hr 6 min•Ep. 390
On this week’s episode, Jared and Jordana start with a recap of Jordana’s weekend with her entire family and Jared’s bloody mary tour of Milwaukee. The first emailer asks if she’s gotten too comfortable being single after a friend told her she feels like she’s giving up. Does she need to put herself out there more or should she continue focusing on herself? The Awkward Sexual Encounter involves a “king size” man and a CPAP machine. Later, J&J listen to a voicemail asking how to approach dating a...
Oct 19, 2022•1 hr 18 min•Ep. 389
J&J are back with another Sunday Special, and this week they're talking about being friends with exes. Jared and Jordana share their own experiences trying to be friends with exes and how that idea changes as you get older. Then, they dive into the email detailing a listener’s relationship with her ex from college. They broke up but stayed in touch through their friend group, and they eventually ended up in the same city again. When she told him she was thinking about getting back together, he s...
Oct 16, 2022•39 min•Ep. 388
Jared and Jordana are back in the studio for this week’s episode, and they start with a recap of Jordana’s trip to Hawaii and a look into her family dynamic with 9 siblings. Jared updates Jordana on his dating goals from his latest U Up? With Benefits episode. The first emailer asks if guys care less once the relationship becomes official after noticing her new boyfriend has been putting in a lot less effort. Should she “match his energy” or speak up about her annoyance? The Awkward Sexual Encou...
Oct 12, 2022•1 hr 33 min•Ep. 387
Jared and Jordana are back with another Sunday Special, and this week they’re tackling the age-old “right person, wrong time” question. The emailer sends in screenshots of the very nice breakup text she received after two great dates. He didn’t want to keep dating because he was moving but told her to let him know if she was ever in his new city. Fast forward a year, and she’s moving there for work, so should she ask him to grab a beer? J&J break down all the possibilities she should think about...
Oct 09, 2022•34 min•Ep. 386
This week’s episode starts with a big shame on Jordana for straying from Delta Airlines for her trip to Hawaii and the Bach By NoonTM plan for Park City. Then they dive right into the second half of your Lightning Round questions about everything from moving in with your long distance S.O. to making a coffee date actually feel like a date. Plus, Jared gives the world’s saddest pep talk. Detours include planning where Jared would move for a date and Jewish mom erotica. Learn more about your ad ch...
Oct 05, 2022•1 hr 1 min•Ep. 385
J&J are back with our first Sunday Special of October, and they start with a chat about Jared’s trick or treating observations from last year and Jordana’s days as a babysitter in the city. Then, they dive into the email from a listener whose husband wants her to lose weight. They’ve both been on their own health journeys, but she’s healed her relationship with her body and he’s still struggling. After he revealed he prefers a thinner body type than hers, she asks if she should try to lose the w...
Oct 02, 2022•34 min•Ep. 384
On this week’s episode, Jared and Jordana are answering your lightning round questions submitted via Instagram, but first they’re breaking down Jared’s adventures in Buffalo and the recent cheating accusations against Adam Levine. Then, they get into your questions ranging from how to stand out on dating apps to how to meet people IRL as an introvert. Plus, they discuss the old line that “the best relationships are when the man loves the woman more than she loves him” and give advice for disgust...
Sep 28, 2022•1 hr 21 min•Ep. 383
Jared and Jordana are getting right into it on the Sunday Special, and this week’s email is about a “somewhat-unsuccessful” trip to visit a long-distance situationship. They go into what you should expect when you’re taking a chance and getting on a plane to meet up with someone. The first night of her visit went great, but the next night felt off and he made excuses to not see her again before she left. She says she got the ick after he needed too much reassurance that she liked him, but J&J ar...
Sep 25, 2022•40 min•Ep. 382
On this week’s episode, Jared and Jordana start with a discussion about interpreting comments from strangers on the internet and getting set up by Jared’s mom. The first emailer writes in to ask if she’s jumping into a commitment too quickly after a long term relationship ended. Should she stick with her goal of staying single for at least a year even if she really likes the guy she’s seeing? The Awkward Sexual Encounter involves way too much tongue. Later, a listener writes in about her boyfrie...
Sep 21, 2022•1 hr 34 min•Ep. 381
J&J are back with another Sunday Special, and they start with a chat about how to enjoy dating on football Sundays. This week’s email comes from a male listener who keeps finding himself in the same dating situation. After about two months of dating someone, he gets a text saying he’s a really nice guy, but they don’t see it going anywhere romantically. Jordana gives the honest version of these texts that he’s not getting. Is there anything he should do differently or is this just a normal part ...
Sep 18, 2022•38 min•Ep. 380
Jared and Jordana are back in the studio on Jordana’s birthday to record the first episode for our new YouTube channel. They start with a discussion about happy birthday etiquette and. Then, J&J discuss a New York Times article all about dating app burnout and how to avoid it. Have dating apps done more damage than good over the last ten years? The Awkward Sexual Encounter involves a very large man in a very small bed. Next, they answer an email from a listener asking if how her boyfriend talks ...
Sep 14, 2022•1 hr 25 min•Ep. 379
J&J are back with another Sunday Special, and this week they start out with a refresher on the “reveal” and what being “exclusive but not in a relationship'' actually means. The emailer writes in about how she regrets responding poorly to a reveal from a guy she was dating. She tried to make up for it, but he ended the relationship a few weeks later. Did she ruin it with her original response to his reveal? Or is she just more attracted to him now that he’s pulled away? Plus, they talk about how...
Sep 11, 2022•40 min•Ep. 378
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•1 hr 30 min•Ep. 377
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
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•1 hr 32 min•Ep. 375
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
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
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
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•1 hr 35 min•Ep. 371
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
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
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
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
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
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
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
