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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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2
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
Mug icon

The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

Buy the mug