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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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.
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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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Poor Dennis is just so excited to have Gary dating his sister and just wants his sister to date a good guy and to have Gary in the family.
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Dennis' sister, Anna, gives Gary a huge hug and he doesn't seem to be hugging back. Anna is definitely what we'd call a stage five clinger.
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A promotional picture of Al Madrigal as Dennis Lopez on CBS's Gary Unmarried. Dennis is Gary's best friend and co-worker.
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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.
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Gary and Allison wake up after accidentally spending the night together to find Allison's fiancee, Walter, at the foot of the bed.
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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!
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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?