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."
Prices shown in USD.
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