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After finding out Jake spent Spring Break with Judith's parents, Evelyn demands that Jake spend the night at her place. Though Alan and Charlie dislike the idea, they drop him off and head to the bars to drink away their concerns.
When Evelyn finds out from the obituaries that her second husband, Harry, has died, she and the family attend the funeral. Charlie ends up hitting on Harry's newly single widow, Jake is excited to see a "dead guy" and Alan is happy to pay his respects.
After Charlie takes Alan to the eye doctor, they end up at the coffee shop where they run into Charlie's ex, Sherri (Jeri Ryan). Alan ends up asking out Sherri, but can't get over her prior relationship with Charlie.
When Judith decides to take a vacation, Alan has to take care of Jake during the week and finds out it's more work than he thought. When his IRS audit forces Charlie to take care of Jake, he doesn't do much better.
When Charlie leaves the house to avoid a date he can't stand, he ends up at the coffee shop where he runs into his old girlfriend, Lisa (Denise Richards), who is now a divorcee with a baby. Jake tries to justify to his father why he isn't doing well in school.
When Alan meets Nancy (Kelley West) at the grocery store, she fulfills all his fantasies, forcing Charlie to take care of Jake while he's distracted. After knowing Nancy for just a few days, Alan decides to ask her to marry him making Charlie to try and stop him, even getting Evelyn to help.