Holly tries every attempt to find out if Henry has a new girlfriend so she can go after Vince. It turns out that Henry has moved on. When Holly goes to Vince's, she finds something she wasn't expecting. Meanwhile, Val and Lauren run into Rick (Val's ex-boyfriend) while they are at the diner. They make lunch plans, and reminisce on old times.

When Holly and Tina are shopping at F&A (Gary's new workplace), Holly meets Greg, Gary's manager. Greg asks Holly out on a date, and she accepts, just to make Vince jealous. Everyone decides that they're going to Holly's house to see a lunar eclipse, and that's when everyone's true feelings come out.

Val meets Rick's fiancee when he and Julie come to dinner. Julie and finds out that she and Rick are not as compatible as she thought they were. Meanwhile, while writing her college report, Holly forgets to save it, and it gets deleted! She asks Henry for help, and he does, which causes him to not meet his idol Bill Joy and receive $10,000 in cash. Holly questions the breakup between her and Henry.

When Holly and Tina don't have dates to the prom, they are upset, so they decide to throw an Anti-Prom, with no decorations, no dresses, and no prom king or prom queen. Everyone who doesn't have a date shows up, but when Henry comes with Kate, Holly is heartbroken. Meanwhile, Val doesn't know what to do when she gets an invitation to Rick and Julie's wedding. She tries to look at the post mark to see if it was sent before Julie's "no contact" rule, but the postmark is smudged.