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

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 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

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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Lovable Dennis

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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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 and Dennis Hug

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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Gary and Anna

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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Al Madrigal as Dennis Lopez

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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Walter Falls Down

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

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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Plummer Cleans Up

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?