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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.
Evelyn buys Alan a sports car and, as Charlie warns him, expects a favor in return. Evelyn makes Alan go on a blind double date with her.
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.
When Charlie and Alan get into a fight, Rose tries to step in and mediate.
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.
Charlie is invited to a party hosted by a gay ad-executive, Eric (David Starzyk), so Charlie brings Alan to pretend to be his life partner until he meets Eric's beautiful ex-wife.
After Charlie has back pain, Alan takes him to the hospital. Charlie ends up hitting on the doctor, who he's already dated. Berta is fed up with Jake's continuous mess in the bathroom.
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.
Alan starts to worry too much about a medical procedure he's about to get, so Charlie tries to distract him by going to Vegas.
Charlie and Alan throw out Evelyn when she insults the way Alan is raising Jake. When their mom ends up the hospital, they're not sure if it's real or a ploy to get back their affection.