Eric flies to New York in a last attempt to convince Chandler's dying father (guest star Dan Lauria) to make peace with Chandler before it's too late. Meanwhile, Matt (guest star Barry Watson) and Sarah (guest star Sarah Danielle Madison) suspect that she might be pregnant and Matt's co-worker lets the news slip to Eric; Lucy fears she might also be pregnant, which causes her to panic and push Kevin away; Mary (guest star Jessica Biel) tries to find Eric to tell him that she did something stupid; Lucy offers her classmate Christine (guest star Tara Lipinski) a temporary place to live, unaware that she's hiding a big secret; Simon is crushed when Cecilia refuses to go to the prom with him; and no one can understand why Ruthie is acting especially strange.