Jared has an awkward hook up after masturbating 700 times. A listener tells the story of watching a gay porn and hearing familiar music, namely the 'U Up' theme song. Another fan asks when the right time to add a dating partner on social media might be. J&J then take a letter about a guy who requested a Venmo refund for a cheeseburger after a first date that went nowhere. Also, is sleeping with a dude on the first date always a bad move? Probably, especially if it's with the guy whose dating profile pics were all taken by his ex.

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Jordana and Jared start off talking about the heart DM on Instagram (is it sincere?). Then they take a letter from a compulsive planner who is curious how far ahead it's appropriate to plan in a dating context. After a listener asks what he should if he's in a long-term relationship (over two years), but he doesn't see it going anywhere. They wrap things up answering whether a dating partner who kisses their family on the mouth is a "red flag or a dealbreaker."

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After talking about various verbal dealbreakers such as “golly” and “oh my gosh,” Jordana and Jared take a letter from a listener asking how to act if she runs into a 25-year-old college student after he ghosted her. They talk about Instagram stalking and other weirdos that linger in the “viewed by” section of social media apps. At 0:47, Jordana is joined by Whitney Cummings. talking about her new film, The Female Brain, and how men and women differ.

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Jared and Jordana talk about how to handle Valentine’s Day as a single person, having reasonable standards, and what men and women have to gain from marriage. After, they discuss people who are resistant to “the apps.” Do you live in the Now? It’s time to get better at dating online— though they’re not sure which gender has it better in our Hinge-driven world. They also respond to a letter from a listener caught between a girlfriend and a dream crush.

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Jordana and Jared have a fascinating discussion about exes, matchmaking, and being nosy about people's relationships. They take two questions posed by listeners. The first comes from a distressed lover scorned by someone who randomly started bringing up their ex. Number two deals with a bizarre boy who switches from smooth Romeo to college frat bro who doesn't want anything serious. And don't miss a classic would you rather: date someone who smokes pot everyday or someone who does crystal meth once a year?"

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This week Jordana and Jared discuss micro-cheating and whether or not men and women can really be just friends. They answer questions from a listener whose boyfriend turns into a caveman when he gets angry and another listener who is offended by the fact that her boyfriend watches porn. They play games involving dating someone with cats and a ‘Live Laugh Love’ sign in their room.

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This week Jordana and Jared discuss how long you should wait before putting the person you’re dating on social media. They answer questions from a listener who wants to know if she should stop having sex with a guy because he’s a Trump supporter and another listener who wants to know what the etiquette is for confirming a first date. They play "Shoot, Fuck, or Marry" and "Red Flag or Dealbreaker" about people who want to be stay at home parents, live off their parents, and have weird voices.

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This week Jared and Jordana discuss if it’s possible to not drink while dating. They answer questions from a listener who wants to know why the guy she slept with texts her all day even though he lives in in another state. They also respond to a listener who is tired of dating girls who are overly sarcastic and not sweet enough. They play 2nd Date Dealbreaker involving calorie counting, over-ordering, and being a messy eater.

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This week Jordana and Jared discuss why a girl might not have sex with a guy she lets sleep over. They answer questions from a listener who wants to know why guys Snapchat her more than they text her and a guy who wants to know if it’s okay to dump a girl he’s been seeing for 4 months over text. They play 2nd Date Dealbreaker involving STIs and farting.

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This week Jared and Jordana discuss why guys like Instagram Models’ photos. They answer questions from a girl who’s anxious she won’t get a New Years kiss and other listeners wondering when an appropriate time to initiate exclusivity is. They play games involving dating a bad tipper and dating a closed mouth kisser.

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