Gary's New Bowling Team

Gary's New Bowling Team

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 at the Opera

Gary at the Opera

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 Make Out

Gary and Ms. Plummer Make Out

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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Gary and Charlie

Gary and Charlie

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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Gary Listens to Louise

Gary Listens to Louise

When Louise interrupts television time by playing her cello, Gary pops in to listen to his overachieving daguther play.
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Taylor the Painter

Taylor the Painter

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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Gary Tries to Dress Taylor

Gary Tries to Dress Taylor

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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Gary Gives Allison the Check

Gary Gives Allison the Check

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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Taylor and the Waitress

Taylor and the Waitress

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 and Taylor

Gary and Taylor

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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Anna the Wife

Anna the Wife

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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Anna Kisses Gary

Anna Kisses 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?
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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?