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 hires the girl at the coffee shop, Lindsay (Delaney Yeager), to spy on Allison's dates while he's at the opera. Here's a picture of him calling with an update.
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.