When you are "dating" a rich older person. This includes either Bagging a Cougar and Finding a Sugar Daddy depending on your gender or sexual persuasion.

Derived from the idea that a Bentley is a nice car driven by rich people and rich people tend to be older. While the tailgating portion of the phrase is used as innuendo for sexual activity.
Bro A: "Dude, I've been Tailgating a Bentley since May."
Bro B: "Nice Bro, does she buy you stuff?"
Bro A: "Of course and I think I'm in love."
by RayzRyd June 17, 2009
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The act of placing a cooked beer brat in your ladies anus, several servings of sauerkraut in her puss and topping it all with a hardy dash of man mayo.

Let sit for 30-45 minutes at 98.6 degress and then feast upon the fruit of your labor.
We went to the Packer game last weekend and I cooked up a dynamite Polish Tailgate. It was cooked to perfection and seasoned properly. It came out extra juicy and the fellas loved it!
by Crazy Driggs February 19, 2011
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To receive anal sex while eating fried chicken.
"Janet is awesome, she had a tailgate special and passed me a drumstick while I was pounding her ass!"
by Nom De Doom October 8, 2011
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Someone you meet and recognize, but your not sure how you know them. If you frequent college football tailgates, chances are your paths have crossed very early on a cold fall Saturday morning.
Jessica: Scott, this is Brad - Brad, this is Scott.
Scott: Brad I think I know you -- you're tailgate familiar.
by gizellelabelle January 27, 2010
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When you are "dating" a rich older person. This includes either Bagging a Cougar and Finding a Sugar Daddy depending on your gender or sexual persuasion.

Derived from the idea that a Bentley is a nice car driven by rich people and rich people tend to be older. While the tailgating portion of the phrase is used as innuendo for sexual activity.
Bro A: "Dude, I've been Tailgating a Bentley since May."
Bro B: "Nice Bro, does she buy you stuff?"
Bro A: "Of course and I think I'm in love."
by RayzRyd June 17, 2009
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Tailgate Tested Tailgate Approved

1. A new product that helps men in their everyday lives to enhance a task often farfetched and strange but useful nonetheless and always good for tailgaiting at Colts games (oh and all the other teams who are not as good as the Colts)

2. BEER COMMERCIAL.
Tailgate Tested Tailgate Approved

The Foozie Foam Finger! Combines an Indianapolis Colts foam finger with a koozie to hold your beer. Because its-

*Crowd*: "Tailgate Tested"

Tailgate Approved
by Cordell Erskin April 28, 2010
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Yo bubba when you gon cut that Mississippi tailgate
by JONTX April 5, 2010
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