Gary's new bowling team consists of his dad, his ex-wife, Dennis (not pictured) and, of course, himself. Seems like a perfectly normal bowling team... for Gary Unmarried.
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.
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?