There have been some changes in Amy's figure since we last saw her—she's gained baby weight and a killer appetite, to boot. To make matters worse, a close encounter of the gas station kind between potential grandmother Anne and Dr. Jean Hightower reveals that Anne is still as clueless as ever. The rest of the town is not, however, thanks to the gossip mill.
Meanwhile, Ben's still working on planning the perfect first kiss with Amy, while Ricky's hatching a plan of his own—a selfless one, for once! He's going to help Grace sneak around behind her parents back by pretending to date her, and then safely escort her into Jack's arms. But is it so selfless? Adrian doesn't seem to think so, but she'd never admit that she's actually jealous.
Later, at the fair, all the usual suspects are coupled up: Alice and Henry, Amy and Ben, and Grace and Jack (hey, he can get over his Ricky hatred if this plan involves make-out sessions). But when Ben tries to kiss Amy after the carousel, she gets a serious case of nausea and throws up all that food she just ate—ew! Talk about ruining Ben's painstakingly planned moment. Looks like the only serious winner at the fair turns out to be Ricky, who scores serious points with the Bowmans when he brings Grace home safe and sound from their "date." Unexpected, right?
But Ben's not willing to give up his romantic vision yet. He shows up at Amy's house and executes that first kiss, flawlessly. All could be well in Amy's world, except that now sister Ashley's figured out she's pregnant and from the looks of it, there's a lot more drama to come before everybody gets to their (hopefully) happy endings. Ashley asks Amy if Ben knows about the pregnancy and she says that he doesn’t and Ashley promises not to say anything to their parents about her being pregnant and they end the episode by Amy and Ashley hugging.
- Shailene Woodley as Amy Juergens
- Daren Kagasoff as Ricky Underwood
- Francia Raisa as Adrian Lee
- Ken Baumann as Ben Boykewich
- India Eisley as Ashley Juergens
- Greg Finley as Jack Pappas
- Megan Park as Grace Bowman
- Mark Derwin as George Juergens
- Molly Ringwald as Anne Juergens
- Steve Schirripa as Leo Boykewich
- Allen Evangelista as Henry Miller
- Amy Rider as Alice Valko
- Josie Bissett as Kathleen Bowman
- John Schneider as Dr. Marshall Bowman
- Andrew MacFarlane as Jason Treacy
- Ernie Hudson as Ken Fields
- According to The Secret Diary of Ashley Juergens, this episode takes place from September 18-19, 2008.