In the magical summer of ‘94, Snoop Dog was climbing the charts, Olympic skater Nancy Kerrigan was clubbed on the knee and 32-year-old Glen Abbott was still living with his parents when the only girl he ever kissed, Alison McKellar, returned to town with her 14-year-old son, Josh. The recently divorced Alison inspires Glen to become a "grown-up" to win her heart. Glen and Josh become fast friends and end up on a double date with Alison and Josh's dream girl.
When Alison invites Glen over for dinner, Glen is elated until a co-worker convinces him that divorcées have urges and he will be expected to "put out." Embarrassed by his lack of a sexual past and fearful it will drive the love of his life away, Glen decides to visit a "massage parlor" to get a quick tutorial before his date with Alison.
With Glen spending more and more time away from home, his parents' marriage starts to unravel. Glen finds comfort in his new surrogate family--his dream girl Alison, her son, and her boyfriend. When it becomes obvious he's overstayed his welcome at Alison's, Glen decides to call his first-ever "family meeting" and get his parents to fall in love with each other all over again.
Alison is unable to accompany Josh on a weekend trip to the State Spelling Bee in Albany, so she asks Glen to chaperone. Since no one knows them this far from home, Glen and Josh decide to reinvent themselves to attract the ladies. Glen wears a toupee and creates the persona of Lance Manley, a studly airline pilot, while Josh pretends to be a cocky multiple-spelling-bee champion.
When Josh starts hanging out with a new friend at school, Glen is determined to find his own new friend. Unbeknownst to Glen, his new friend is a gay man with a smoldering crush on him.
When Glen poses as Josh's "dad" for a parent-teacher conference, he comes face-to-face with his old homeroom teacher, Miss Burko, who ends up giving him a private, albeit very belated, lesson in love.