tangle, v. — Green’s Dictionary of Slang

tangle v.

1. to add alcohol to a drink.

1835		J.P. Kennedy Horse Shoe Robinson I 256: Some water, Mr. Musgrove, and it will not come badly to my hand if you can tangle it somewhat [DA].
1840		J.P. Kennedy Quodlibet 126: Bring us a tumbler of water — tangle it [DA].

2. see tangle assholes

In compounds

tangle-monger (n.) [SE tangle, a knotted mess + -monger sfx]

(UK society) a woman scandalmonger.

[1616		W. Haughton English-Men For My Money F2: These horeson Canniballs, these Philistines, Those tango mongoes shall not rule Ore me, Ile have my will and Ned, or Ile haue none].
1909		J. Ware Passing Eng. of the Victorian Era 241/1: Tangle-monger (Soc., 19 cent.). Application of word ‘monger’. Speaks for itself – an individual, generally a woman, who fogs and implies everything.

In phrases

tangle assholes (v.) (also tangle, tangle-ass, tangle holes) [asshole n./ass n. (2)/hole n.¹ (1a)]

(US) to fight.

1934		(con. 1920s) J.T. Farrell Young Manhood in Studs Lonigan (1936) 191: I just tangled holes with some fluky-looking wiseacre.
1950		Goldin et al. DAUL 220/1: Tangle ass. To become embroiled in a fight or heated argument.
1953		W. Hopson ‘The Ice Man Came’ in Thrilling Detective Winter 🌐 If it’s because Joe and Ace are about to tangle over you, forget it.
1960		P. Rabe Murder Me for Nickels (2004) 119: ‘Check out Benotti for me.’ ‘You want me to tangle...’ ‘I don’t mean that.’.
1974		G.V. Higgins Cogan’s Trade (1975) 46: I’m not going inside and tangle assholes with that monster.
2000		G.V. Higgins At End of Day (2001) 31: Guys that look like they could tangle assholes with a buncha paratroopers.

tangle with (v.)

1. to fight with; lit. or fig.

1913		S.F. Bulletin 6 Mar. 16: Just let us tangle with Ed Walsh and these Chicago fellers a few times.
1923		D. Hammett ‘House Dick’ in Nightmare Town (2001) 48: Not the kind of egg you’d want to tangle with.
1934		(con. 1920s) J.T. Farrell Young Manhood in Studs Lonigan (1936) 370: He supposed he’d have to tangle again with Weary sooner or later.
1943		W.R. Burnett Nobody Lives for Ever 88: ‘[L]isten; don’t tangle with the big fellow. Keep your nose clean. He’s a good-natured guy but he’s no one to cross’.
1951		M. Spillane One Lonely Night 16: They’re scared to death to tangle with me.
1959		J. Thompson Getaway in Four Novels (1983) 7: Doc was too smart to tangle with Rudy Torrento.
1966		W. Wilson LBJ Brigade (1967) 27: They’ll kill the poor civilians but they won’t tangle with us.
1976		N. Thornburg Cutter and Bone (2001) 294: People who ‘shoulda knowed better than tangle with an officer with twelve-inch wrists.’.
1993		K. Scott Monster (1994) 153: If he had any further notions of putting hands on me, he’d have to tangle with my gun.
1994		G. Disher Crosskill [ebook] ‘So he’s bad news, not someone you’d want to tangle with’.
1999		L. Gould Shagadelically Speaking 6: They take the flight in order to tangle with Dr. Evil on the moon.

2. (also tangle up with) to become involved with.

1938		D. Runyon ‘Undertaker Song’ in Runyon on Broadway (1954) 332: It seems that she is once tangled up with Joey Perhaps.
1940		D. Maurer Big Con 181: You tangle up early with guys who cheat for a living.
1966		R.H. Rimmer Harrad Experiment 107: Let’s get the hell out of here. I don’t want to get tangled with the fuzz.
1975		Sepe & Telano Cop Team 27: The City cop who had tangled with Telano soon found Sepe.
1987		T. Wolfe Bonfire of the Vanities 37: He’d be the last person they’d choose to tangle with.

3. to meet.

1977

K. Gilbert Living Black 147: I tangled with Charlie Perkins, the Minister for Aboriginal Affairs, [...] the Minister for Everywhere was there! I met the lot!