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Jane Kaczmarek guest-starred this week as a businesswoman who Ryan hit with his car. But he couldn't afford to pay the damage, so Wilfred helped him seduce the lonely lady instead.
Ryan was grossed out by the entire charade, but too proud to ask his sister for financial help. As a result, he made out with Kaczmarek's character and got her into bed, only for her to fall asleep. But Wilfred later came in and went down on her, much to her pleasure, thinking it was Ryan.
Meanwhile, Wilfred was having sex with this woman's stuffed animal giraffe. He liked it more than Bear, until the giraffe got too kinky and scared him away.
In the end, both Ryan and Wilfred were appalled by their actions and the former decided he wasn't too proud to ask his sister for financial help after all.