After months of flirting via e-mail, 12-year-old Emma's new love interest, Jordan, is going to be in town. Coincidentally, it's the same night as her mother's high school reunion. After much consideration and some advice from her mom's friend Caitlin, Emma decides to go for it without telling a soul, even her friends.

Things are pretty hot between Craig and Ashley, but he's disappointed that she keeps pulling back from going all the way. She wants to know Craig loves her, and since he is unable to express himself in words, Craig pours his heart into song. With her heart melting, Ash decides she's ready. An exuberant Craig can't help sharing the news with Spinner, whose innuendo-laced jokes cause Ash to call the whole thing off. Craig storms out followed by Manny, who offers Craig a sweet, supportive shoulder to cry on. Soon, Craig and Manny are caught up in the moment—a moment that goes farther than either of them anticipated. Worried about her husband's deteriorating spirits during his chemo, Spike enlists Joey's help in cheering him up. Reluctantly, Snake joins Joey for a night of bowling and is definitely not impressed when his troubled high school buddy Wheels shows up – until he shares how he dealt with his own checkered past.