Speaking of Sarah, she's working out with a punching bag, taking out her aggression while she visualizes the jerks from her high school. A jock tells her to let him know if she ever needs a man now that her dad's not around. And Heather looks on and laughs. Sarah's interrupted from this lovely stroll down memory lane by Chuck, who has a present for her. But it's not really a present; more of an "assignment." It's a pretty dress for her to wear to the reunion. She is not pleased, since the people at the reunion are the people who were just making her kick that bag with such force. This is where Sarah apologizes for being so mean to Chuck about her past, but high school was really bad for her. He thinks he gets it, and cluelessly compares her high school life to his, what with the raging hormones and awkwardness. She says sadly that it was more than that for her, and Chuck tells her it will be okay, because everyone remembers high school worse than it was.
That's the perfect segue for the Backstreet Boys to sing us into the reunion and its really terrible high school pictures. Were we really that terrible-looking in the '90s? That wasn't that long ago and I don't remember being such a fashion disaster. People are all shocked at how much our little Jenny Burton has changed into this smoking hot creature standing before them. Chuck gives her a pep talk, and then sees her horrible photo, and lies that it's not that bad. But even he isn't nice enough to make that lie seem true, because ... it's really bad. They washed it out or something for effect, because it's not possible for Sarah to actually look that bad, even in her frizzy hair and braces. This is much, much worse. We get a class of '98 banner, and I feel incredibly old. I guess I thought Sarah was my age or a little older, but apparently she's a couple years younger than me. And now Hanson's playing, as the dick who offered himself up as the man for Jenny in high school checks her out as she walks by with Chuck. She also sees Heather, who's still a bitch. Chuck is offering to show Sarah his '98 dance moves, which are so cute, when Dick (that's the dick's name; go figure) walks up and puts a stop to it with a skeevy pick-up line. Chuck's like, "Uh, hello? Boyfriend! Right here!" And then Dick tells them that Sarah's dad's in prison. Chuck doesn't have time to ask about it or even register shock because he flashes on Dick's tattoo. He's "paroled" and a member of the Russian mob, apparently. So Chuck tells Sarah he must be the guy Mark's supposed to meet with. She doesn't question it since he's always been a dick. Sarah tells Chuck to go let Mark know and she'll tip off the DJ, who is ... Casey. How much do I love that Casey has been spinning tunes by Backstreet Boys and Hanson and that he's dancing along, totally into it? More than should be allowed, frankly. I heart Casey even more than before. We need these little glimpses of humor and/or a heart to make Casey something more than just the big, bad tough guy who could almost kill Chuck when ordered to (although I think he could not.)