Green’s Dictionary of Slang

1. to conduct a promiscuous sex life.

1926		Odum & Johnson Negro Workaday Songs 87: I got a gal, you got a gal, / All us niggers got a gal. / He fool ’roun’, I fool ’roun’ / All us niggers fool ’roun’.
1969		U. Hannerz Soulside 89: [W]ife and older children may shun the husband and father who is a ‘fooling [sic] around,’ while he [...] continues to find little satisfaction in family life.
1974		D. Mamet Sexual Perversity in Chicago (1994) 76: You mean fooling around! Sure, who didn’t. Shit, we all used to fuck about.
1989		C. Hiaasen Skin Tight 271: You knew about all his fooling around.
1993		Pensacola News Jrnl (FL) 4 Oct. 10/3: I firmly believe a lot more people fool around these days than smoke.
2005		L. Theroux Call of the Weird (2006) 104: He was fooling around, too. He got into fornicating.
2010		(con. 1973) C. Stella Johnny Porno 168: He would fool around when somebody new cauight his eye.

2. to enjoy sexual activity short of intercourse; thus the invitation let’s fool around, a suggestion by one of a couple that they should abandon speech for (sexual) action.

1931		Blanche Calloway ‘Just a Crazy Song’ 🎵 Now, I get so hot and bothered when / You start foolin’ ’round.
1934		Z.N. Hurston Jonah’s Gourd Vine (1995) 45: If you’ve been fooling around Duke’s wife, leave her alone.
1951		M. Spillane Long Wait (1954) 105: The dames they get for waitresses in the joints around here are never too careful who they fool around with.
1959		W. Brown Teen-Age Mafia 34: You and me, we ain’t done nothing but fool around like a couple of babies.
1966		(con. 1958) R. Farina Been Down So Long (1972) 94: You feel like dancing, maybe fool around a little?
1975		J. Wambaugh Choirboys (1976) 170: Only fooled around with him a little.
1988		N. Eastwood Gardener Got Her n.p.: ‘Okay, I hear you,’ he sighed. ‘We won’t go all the way. But we can fool around a little, can’t we? No harm in that.’.
1989		M. Amis London Fields 281: Last night she took my hand on the stairs and said, ‘You want to fool around?’.
1993		M. Myers et al. Wayne’s World II [film script] Garth: If you fool around with a girl, does that mean you have to get married?
2000		B. Wiprud Sleep with the Fishes 147: How long would it be before they could fool around?

3. (also fool with) to have a sexual relationship; to have sexual intercourse.

1930		W.R. Burnett Iron Man 282: I might know where you been [...] Fooling around with some woman.
1937		R. Westerby Wide Boys Never Work (1938) 154: He’s been fooling around with old Bill’s missus.
1948		(con. 1944) N. Mailer Naked and Dead 16: When I think of my wife fooling around probably right this minute.
1957		Warren Smith ‘Red Cadillac And Black Mustache’ 🎵 Triflin’ baby are you being true / Who’s been fooling around with you?
1965		A. James America’s Homosexual Underground 39: I hadn’t fooled around much, but I wasn’t exactly a virgin.
1972		J.E. Franklin ‘The Enemy’ in King Black Short Story Anthol. (1972) 350: It did them no good to deny that they had ‘fooled’ with her.
1977		A. Hoffman Property Of (1978) 53: It’s no secret you’re fooling around with McKay.
1997		C. Hiaasen Lucky You 142: He asked Champ Powell what he would do if it was his wife fooling around with another man.
2013		W.D. Myers Cruisers: Oh, Snap! 94: [H]e thinks I’m fooling around with his daughter’.

4. to tease.

1951

M. Spillane Long Wait (1954) 93: They scram. No fooling around. Not if they want to keep their own teeth and noses.