When Allison's brother, Taylor, manages to get Gary a check instead of him paying money during his audit, he just hands the money over to Allison since it'll inevitably go there.
Gary cannot believe the news he hears when his ex-brother-in-law, Taylor (Matthew Lillard), lost all his money and thinks Taylor's ex turned out to be trans... trans... transfered.
Gary is very depressed as his one time fling with Anna quickly develops into some sort of psuedo marriage. Here's a shot of Anna coming to Gary's work, bringing him lunch.
Poor lovable Dennis shows up at Gary's with a six pack of beers and is shocked to find his little sister, Anna, locking lips with his best friend Gary.
Sure Gary tries to resist Dennis' little sister, Anna, kissing him, but when a hot, younger girl shows up at your house in a little skirt, what choice does a man have?
After Walls falls down the steps, Gary and Allison join him at the bottom and they all discuss whether things are working between him and Allison or not.
Louise's "unattractive" teacher Ms. Plummer sure does clean up nicely as she goes on a date with Gary. She also used to be a championship boxer. Have fun!