What is Tailgating A Bentley?
1.
When you are "dating" a rich older person. This includes either Bagging a
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."
See
2.
When you are "dating" a rich older person. This includes either Bagging a
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."
See