- Single for the first time on Valentine's Day, Jess convinces Schmidt to be her wingman as she attempts to have an attachment-free fling with a handsome stranger. Nick's romantic plans are foiled when he finds himself spending more time with Julia's law firm assistant than with her. Winston becomes one of the girls when Shelby invites him over on the holiday.—Fox Publicity
- Nick and Julia are all kissy face on Valentine's Day. Jess is not. "Lucky us, we get to go out looking for some strange, happy Valentine's Day, player," she tells Schmidt. He thinks it's too easy to go out on Valentine's, but she's feeling all "twirly".
Julia and Nick make plans. Last Valentine's he was fighting with Caroline about how he makes too much money and dresses too nice and is too good about communicating his feelings. This year, he tells Julia she'll need a map of Arizona and a container she's comfortable peeing in.
Winston is going to just hang out with Shelby, their first date.
Jess packs an overnight bag in case she has one night sex. It includes a sewing kit and stain remover. She's ready to try a one-night stand, even though Ce Ce is sure she's not up for it. Ce Ce texts Kyle to meet them at the bar. Jess puts perfume all over, not sure who's smelling what tonight.
Nick goes to Julia's office and with his shoulder bag, Julia's intern Cliff takes him for a bike messenger. He offers that, despite the age difference, he would still "hit that" and take Julia to "pound town". Julia introduces Nick as her boyfriend. Oops.
Julia went all out with V day stuff, including heart boxers for Nick that he immediately puts on over his clothes. But she has an hour more of work to do.
Winston arrives at Shelby's ready for some alone time, but he finds ladies on the couch doing their toenails.
At the bar, Schmidt and Ce Ce observe Jess trying to flirt. They call her off when she connects with a guy about being from Oregon. Schmidt offers advice, he's an expert because he has his 10,000 hours -- per "Outliers". It's one of his desert island books, along with Machiavelli's "The Prince", any of the scripts from the first season of "Vampire Diaries" and "Phantom Tollbooth".
Jess heads back into the fray, sitting down next to a guy at the bar and trying to get the cherry out of his drink. She chokes. An absurdly hot guy (Ryan Kwaten) slaps her on the back.
She brings Oliver over to meet Schmidt and Ce Ce. He's a web creator and they both love lunch. He offers her another drink and she gives him her "His Gal Friday" voice, which he doesn't get. He heads to the bar. "Yes, I have no emotional connection to him at all! But I'm just going to eat lunch off that butt," Jess announces.
Schmidt long-distance flirts with a girl. Ce Ce tries to help by making her jealous, draping herself over Schmidt. The moment is ruined when Kyle arrives, having just eaten three 'shrooms. Ce Ce knows it's time to go because he's about to get real antsy and a little racist.
Jess comes back and announces she's ready to go home with Oliver. He's described every lunch he had this week and three of them were tacos, he's the most boring person she's ever met. She has a 100 box of condoms, just in case. But she needs a ride.
Nick and Cliff share a bottle of champagne as Julia does business on the phone, saying it's be going to be another 45 minutes.
Winston calls, knowing he should leave, but wanting to spend time with Shelby.
At Oliver's house, he, Jess and Schmidt watch moves on the couch. Jess texts Ce Ce, complaining that Schmidt is still there. When Oliver heads to the bathroom CeCe calls, telling him to leave. He's worried that Jess doesn't have a ride home.
Jess finally kicks Schmidt out, but he finds that the tires have been stolen off his car. He blames "youths". Nick keeps drinking champagne with Cliff, who asks why he dropped out of law school. He explains that it got real weird after, he went to Mexico and tried to enter a cockfight as a person.
Cliff suddenly announces he doesn't want to be a lawyer either. Julia comes out and Cliff announces that he doesn't want to do her filing anymore. He storms off. Now Julia has to do everything. She tells Nick to go home, she'll call him tomorrow.
Jess and Oliver are making out on the couch when a blonde comes home. It's Amy, his ex. They broke up last week but she can't afford to move out because she doesn't work. CeCe comes in, looking to give Schmidt a ride. He comes in, announcing that his tires were stolen. Then in comes Kyle, still on shrooms. Amy interrupts everything by making out with Kyle. CeCe pulls her off and they start fighting. Schmidt picks CeCe up and carries her out.
At Shelby's Winston gives girl advice.
Jess tries to make out with Oliver, but they're distracted by Amy at the table, eating chips loudly. Jess calls things off and Oliver starts crying about missing Amy. She's just in the kitchen.
Julia comes out of her office to find Nick has done all the filing. There's a photocopy of his butt somewhere in the recycling bin, he was in a mood. She can't believe what he did. They both admit they never cared about Valentine's Day before.
Julia starts kissing him, but they're interrupted by her work call. She takes it, apologizing.
Shelby says good bye to her girlfriends. Winston admits he wasn't expecting a girl's night. Shelby tells him he keeps making up for how he used to be. Valentine's Day 2008, he said he'd call and never did. He knows he doesn't deserve a second chance. But she gives him one anyway.
Jess comes home. She helped Oliver get back together with his ex-girlfriend and video chat with his mom. Schmidt tells her it's for the best, she doesn't want her first one nighter to be with a total stranger. He hugs her and she notices he smells good. He tells her not to overthink it and heads to his room. She thinks about it. Then tells herself not to overthink it. She goes for her 100 box of condoms and heads for his room. She stands outside the door and says his name. Nick comes up behind her. She drops her box of condoms and Nick realizes what she was about to do. She back pedals. They pick up the condoms and he scolds her, carrying her away.
In Schmidt's room, he and CeCe wonder what all the noise is. Her shirt is already off. She tells him if anyone finds out she's going to tell them he drugged her. He's cool with that. They get back to it.
In the morning, Jess talks on the phone with someone, confessing she almost did something really dumb last night. she confesses she almost tried to hook up with Schmidt last night. cut to CeCe on the phone, whispering in bed next to Schmidt. She says hooking up with Schmidt would have been crazy.
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