Eric gives Annie his manuscript to read but she's not happy to learn that he's been spending his time writing smut instead of his comeback sermon for the church. Meanwhile, Simon and Cecilia discuss having sex for the first time and naively share the news with their parents---which doesn't go to well when Cecilia's father finds out. Lastly, Lucy sets out to spy on Roxanne and Chandler on their first date.

Eric flies to New York in a last attempt to convince Chandler's dying father to make peace with Chandler before it's too late. Meanwhile, Matt and Sarah 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 tries to find Eric to tell him that she did something stupid; Lucy offers her classmate Christine 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.

Unable to convince Chandler's father to see his son before he dies, Eric is forced into tricking him. Meanwhile, Eric, Annie and Sarah's mother Rosina get together to surprise Matt and congratulate him on the wonderful baby news. Mary confides a big secret to Lucy. Simon gets turned down by a potential prom date. Ruthie gets her period and tries to hide the news from everyone. Kevin recognizes Lucy's house guest Christine as a girl who was previously arrested for prostitution. Lucy takes a home pregnancy test without telling anyone. Lastly, bad news arrives on the Camdens' doorstep.

Ruthie is on cloud nine when an emotional Eric and Annie reluctantly agree to let her go on her first official date. However, Ruthie isn't surprised to find the family handling her big news with their usual crazy Camden ways: Annie and Lucy decide it's their job to help Ruthie prepare for her date with Vincent (guest star Thomas Dekker); Kevin takes it upon himself to give Ruthie ""the talk""; Sam and David change into their Sunday best so they can go on the date as well; an overprotective Martin and Mac (guest star Kyle Searles) decide to spy on Ruthie and Vincent's date; and Matt volunteers to play chaperone, but finds himself in a web of lies to protect Ruthie's feelings.