It's the end of summer, and Seth convinces a reluctant Ryan to plan a trip to Tijuana, where hundreds of rowdy teens congregate to indulge in escapist excess before they have to begin school again. In addition to dating Luke again, Marissa is angry with Ryan after witnessing him with an older woman. She also wants to stay home and take care of her overstressed father. But Summer persuades her to come, and the four kids drive south, Ryan and Marissa not speaking to each other and Summer and Seth sparring constantly. During an argument, Seth accidentally drives off the road and damages the car. The friends are forced to stay in a disgusting motel overnight while the car is being repaired.
Meanwhile, Jimmy and his wife, Julie, have decided to get a divorce. With Julie and their youngest girl away for the weekend, Jimmy plans to move out and then tell Marissa and her sister about the divorce. Kirsten helps Jimmy paint the interior of his new place, and they reminisce and wonder what would have happened if they had gotten married. Impulsively, Jimmy kisses Kirsten, causing a very uncomfortable moment. At the same time, Sandy seriously considers a lucrative job offer from a very attractive and flirtatious former colleague, Rachel Hoffman (recurring guest star Bonnie Somerville), at a large law firm. Although he fears giving up his ideals, Sandy feels that his marriage is suffering because of his financial dependency on Kirsten.
Jimmy calls Marissa, who is still at the motel with the others, and tells her the bad news. The others try to comfort Marissa, who decides to continue on with them to Tijuana to forget her troubles. Unfortunately, she finds Luke kissing and groping her manipulative friend Holly (recurring guest star Ashley Hartman) on a dance floor, and, devastated, steals some painkillers from Summer's purse and takes them with tequila. Later, Seth, Ryan and Summer are horrified to find Marissa unconscious in an alley, and they frantically try to get help as the party rages around them...
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