He persuades her to go out together on Valentine's Day.Things fall apart when she becomes too uncomfortable during the date.At first things go well, but Adam becomes jealous when Sam (Ben Lawson)—another resident—seeks her attention.
Meanwhile, Emma is depressed over not being with Adam.
The situation is compounded and complicated by her younger sister Katie's (Olivia Thirlby) wedding the next day and her widowed mother (Talia Balsam) arriving for the event with a male companion (Brian Dierker) of her own.
Adam goes in to visit Alvin who surprisingly gives him some tender advice about falling in love.
Shira tells Emma about Adam's dad being admitted to the hospital.
Her plans are ruined – and she has to hide to avoid being seen—when he arrives home with Lucy.
Emma assumes Adam has a new girlfriend and tearfully drives away.
Vanessa calls Adam before he and Lucy can have sex—Alvin has overdosed on a cough syrup-based drink called "Purple drank".
Meeting Adam outside the hospital, Vanessa says that she is ending her relationship with Alvin and leaves for a party.
As Adam leaves the building he calls Emma and tells her that she must be present if she is going to say that she misses him.