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Tailgating a Bentley

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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Tailgating

verb
Present participle of tailgate

1. Something that monkeys who have no idea how to properly drive do in which they drive dangerously close to the car in front of them for no apparent reason.

2. Attending a sporting event, but instead of watching it in person or on a TV at home, combining the two by watching said event in the parking lot of the arena/stadium on a TV in the back of a pick-up truck while eating shitty barbecue.
1.

Person A: Did you see that fucking ape that was tailgating me the entire way here even though I was going 70 mph?!?
Person B: Yeah what a dumbass, I don't understand why some people think driving up other cars' asses will make them go faster when all it really does is increase the chance of an accident.

2.

I can't find a damn parking spot because so many are taken by tailgaters! If they're gonna watch the game on a TV why not just do it at home?!!?
by Wotinacceleration April 6, 2017
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Related Words

Tailgating

Following a man around a locker room while being nude and having a boner, Hoping that he'll get mad, and "slam on his brakes " so you can make your move on his anus.
I totally tried tailgating that cute guy at the gym.
by Waynezuba December 4, 2016
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Bright Eyed and Bushy Tailed

To be wide awake, not tired... old western slang
Woman: Baby are you tired?
Man: Nah, I'm bright eyed and bushy tailed
by Kelly L August 24, 2005
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messy tails

The furry known as "Messy Tails" or "Brown nose pup" who ate is feces and either went to a mental asylum or died.
"Ya know messy tails?"
"No, why?"
"He is disgusting and eats crap"
"Like what crap?"
"Literal crap...Feces"
"I hate him"
"Me too"
by Messytails November 30, 2019
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Tails

Tails is Sonic's Friend. He is r0r0xs. Tails pwn over KN in ize irc!
Tails is a good boy!
by Tails March 12, 2005
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Blind tailgunner

A dark room, full of people, similar to pin the tail on the donkey, except sexual.
I would never take my wife to a blind tailgunner party; I've got to kiss that mouth!
by Joey48442 September 13, 2013
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