We meet 17 members of the Oak Park and River Forest High School (Illinois) graduating class of 1992 as they gather 10 years later for a reunion in Maui.
Mike and his ex-wife Lana feud, Kat tells her former classmates that she is a lesbian, and Matt, newly widowed, considers dating Yvette.
The tranquility of the reunion is disrupted as three former classmates join the group. Meanwhile, Matt and Yvette's budding romance seems to be picking up steam, Mike and Lana deal with their past relationship problems, and Kat considers starting a lesbian romance.
Steve, who had an affair with Matt's ex-wife Lana joins the reunion. Meanwhile, Justin is nervous over his meeting with his longtime high school crush, and Sean's revelation surprises Kirstin.
Several confrontations arise between Mike and Steve, who had slept with his ex-wife. Lana is jealous when Heather arrives, Matt and Yvette have their Hall Pass, a flag football games is created when the class of '86 women crash the reunion to take on the class of '87.
Steve makes one last attempt to make up with Mike, which causes Lana to make a surprising announcement. Yvette is confused by Matt's reaction after telling him her secret.
It's an unforgettable season finale as a surprise guest arrives for the prom. Meanwhile, Justin is unsure about continuing a relationship with Deanna, and several other couples decide whether to remain so or not.
15 classmates of 1988's Chandler High School in Arizona, reunite at a mansion in Hawaii.
When the classmates return to the beach, they discover their reunion will now have a pair of troublemakers, which may cause one participant to leave, due to their offensive behavior.
The classmates have had enough of Dennis' behavior and hold a vote on whether to let him stay or make him leave. Meanwhile, Scott H. brings Kara out on a Hall Pass, which makes her ex-husband wonder why. Also, Lynette discovers she has a secret admirer.
Emotions have peaked as the class debate whether to kick out Dennis from the reunion. Elsewhere, Jen and Liz's bitterness between each other increases; and Lynette's secret admirer discloses himself.
Liz and Jenny are sent to detention, forcing these bitter to talk with each other. Andrew receives advice from an unlikely pair where he gains confidence to ask out his secret crush. Tom and Kara's chance of reconciling hits a snag.
A spirited charge is felt throughout the reunion when a new classmate, Octavia, arrives. A startling revelation is revealed as Tom and Kara's Hall Pass ends. Jessica lashes out with some shocking allegations as her emotions get the best of her.
Having suffered an emotional breakdown, Jessica answers her fellow classmates questions about her behavior and makes a final choice about whether she is leaving or not. Meanwhile, a romance may be in the offing between Maricela and Scott W.
Season 2 finale finds the classmates laying down sleeping bags on the football field for a "good-bye" slumber party. Meanwhile, Scott W. thinks about a relationship with Maricela, while Tom and Kara stay behind to decide on their future.
At the 20th high school reunion, a football star reconnects with his former flame and cliques reform.
John says the unspeakable to Marcel; Tracey encourages Antanus to propose.