noun; A person who was very popular, happy, and had tons of friends as a child but grew up alone and jobless. Usually ends up turning to drugs for comfort.
Friend 1: Remember that one kid from high school, Alex, I think? That kid was craaazy, we had some fun times with him!
Friend 2: Dude that kid was always the life of the party! What ever happened to him?
Friend 3: I saw him in the paper for possession of cocaine and marijuana.
Friend 2: Wow, what a Macaulay Culkin.
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To call someone on the phone.
"I'll Macaulay Culkin you around 9."
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A sexual act whereby an angry woman takes a man's seed in her hands, spreads it around them, and slaps it on the man's cheeks, resulting in his scream similar to the famous scene from Home Alone.
That asshole cheated on me! Well, the joke will be on him when I pull a reverse Macaulay Culkin!
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The masturbatory act one performs only and just because is home alone.
- What did you do on Friday?
- I had no money to go out and my parents went to a funeral outside the city, so I just went for a good 'ol Macaulay Culkin.
When your having sex with a girl or guy(whatever your into) pull out before you but an blow it in your hand rub them together and slap partner on each side of the face.
Dude I did The Macaulay Culkin to this girl last night.