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.
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Gary goes on a date to the opera with Joan (Kathleen Rose Perkins). Gary's just hoping to get lucky like all the guys at the opera.
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Gary and Ms. Plummer (Kathleen Rose Perkins) make out on the coach while Allison walks in on them. Great timing Allison!
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Allison's father, Charlie, begs Gary to go behind Allison's back and make Louise play golf so she can buy them nice things when she makes money.
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When Louise interrupts television time by playing her cello, Gary pops in to listen to his overachieving daguther play.
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Gary hires the formerly successful, financial whiz, Taylor (Matthew Lillard) as one of his painters on his paint job. Poor Taylor.
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When Gary's ex-brother-in-law, Taylor (Matthew Lillard), is too depressed to put on pants, Gary desperately tries to get him to put on some underwars.
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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.
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Gary gets angry as his pompous ex-brother-in-law Taylor (Matthew Lillard) hits on their waitress at dinner they went to.
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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.
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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.
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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?
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Gary Unmarried Quotes

Louise: Thank you dad, you restored my faith in men
Allison: What'd he do? Wear pants to go get the mail?

Ms. St James: If we're going on a date you should call me erica
Gary: But can I call you ms St James on the date cause that's kinda hot?