Neurotic Nate has an amazing a blind date with eccentric Marni, but they gradually come to realize that their friends actually set up the blind dates with two other people who are patiently waiting for them in Marni's lobby.
Nate decides to surprise Marni at work with a cup of tea, but confusion abounds since he's not the fictitious boyfriend whom she'd bragged about to her coworkers. Meanwhile, Bowie records an embarrassing song for his mother, and Tess hires Clown to entertain at a birthday party.
The morning after they first have sex, Nate finds himself stuck in a bizarre soap opera with Marni and her deadbeat dad. Meanwhile, to make up for losing Bowie's keys, Tess teaches him the power of carrying a baby bag.
Nate and Marni lock themselves in her apartment for a week in an attempt to detox from life in Manhattan, but Nate quickly becomes starved for news and Marni is compelled to play in the falling snow. Meanwhile, Bowie is hesitant to break up with his girlfriend because he's in love with her bed.
Marni's not bothered that Lily, Nate's mother, is residing in a fancy mental institution, but she is bothered by the fact that Lily doesn't like her. Meanwhile, Clown finds respite from the closet by lounging in the hallway, Tess fawns over a new tenant, and Bowie fixes up his grandmother's scooter.
Bowie is owed a $29 burger from a bet, but complications arise when Nate tries to give advice to a homeless man who's panhandling in the ATM vestibule. Also, Marni inherits a veteran's purple heart, and Tess accidentally gets a kid drunk.
In an attempt to steal Marni away, Todd introduces Nate to woman with whom he has a lot in common. Meanwhile, Bowie lands a job performing the National Anthem at a pee wee basketball game, but his already low self-confidence plummets when Tess points out that he grabs his crotch every time he sings.
After getting drunk with Todd, a hung over Nate wakes up in Natalie's bed, with no memory of what happened the night before. Nate panics and heads to Marni to assure her that nothing happened between him and Natalie. He asks that she believe him and Marni decides to take his word. Nate, unsure of what really happened, decides to go back and ask Natalie about the night's events. Elsewhere, Tess baby sits a new kid, Zach, who asks her to pose nude for his friend. Meanwhile, Bowie decides to promote his new CD at the marathon, using paper cups to advertise its release.