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An expression used when pointing out something interesting noticed.
Well, I wouldn't lick a grapefruit, but his forehead is pretty massive.
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when a girl squirts an excessive amount of pussy juice therefor acting as a grapefruit when you squeeze it.
Your mother squirts like a grapefruit when im busy fucking her. She squirts so much i think i'll make a pussy juice cocktail tonight.
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To prepare and take a line or lines of coke off of the balls of a gentleman over the age of 45
Hey mate, mind if I dust up your grapefruits?
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The person has fallen from grace. They’re not as good as they used to be.
Look at them, this is so sad. Oh, how the grapefruits have fallen!
Beyond even a lemon on the citrus scale. This is reserved for the lewdest of the lewd fanfics. The kind with fetishes not even DeviantArt would allow. Some time’s there’s barely even a plot, just nothing but the author’s oddly specific and/or gross as fuck fetish and copyrighted characters participating in them. You, a person finding such a fanfic, were either looking for it or you made the mistake of asking for context when somebody joked about the grapefruit.
If you go out and pick grapefruits, be warned that Rule 36 will be constantly proven to you the hard way.
Bob: Alice’s Harry Potter grapefruit is something else, man. What perverted mind wants to read about Hermione getting a Manhattan transfer from Luna?
David: A Manhattan what-now?
Bob: You don’t want to know.
Used to describe one who is extremely passive, diffident, and introverted. Usually very bad at socializing.
That guy can't talk to anyone without having a panic attack. What a grapefruit.