When a man wakes up in the morning to a woman performing oral sex on him.
Man! I feel great! I woke up this morning with a head start!
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When a person wakes up in the morning to another person performing oral sex on them.
Dome in the morning? Boy, you know I love a head start!
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when a man dates/marries a girl who already has children with another man so that he can avoid an annoying part of having babies (changing diapers) or have children older than all of his friends
Ex 1.
Dude 1: Yo, is that Tom with Angela?
Dude 2: Yeah, they've been dating for two years.
Dude 1: Why do their kids look like they are 6 years old.
Dude 2: Oh, that's from when she was boning that emo dude and got pregnant right out of high school. Tom decided he hates being thrown up on so he opted for a girl who could give him a head start.
Ex 2.
Dude 1: Gary's kid is such a prick. One day my kids will whoop his ass.
Dude 2: Gary's boy is 16, how are you gonna do that?
Dude 1: I'm going to get a head start with a white-trash MILF.
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A word pertaining to anyone who has a huge head start or lead over another person; particularly meaningful when talking to a person residing in or around Great Britain that has a 5 or more hour handicap over another person from another country.
Guy A : I won the race!
Guy B : Dude, that isn't fair, you had a British head start
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Hym "How'd you get a 2 year head start Sam? Ooooooh! Right... Greatest mind who's ever lived locked in you basement... Right..."