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Green’s Dictionary of Slang

hassle v.¹

1. (orig. US) to annoy, to nag, to pressurize; thus hassling n., nagging.

1959		L. Lipton Holy Barbarians 185: My old man and my old lady [...] hassle me all the time.
1967		H.S. Thompson letter 2 Oct. in Proud Highway (1997) 641: The Times is hassling me for that Tahoe piece.
1979		L. Bangs in Psychotic Reactions (1988) 272: Every fucking place you go you get these cats hassling you.
1979		Lette & Carey Puberty Blues 30: After two week-ends of hassling we finally got the boards for half an hour.
1994		G. Disher Crosskill [ebook] I’m ‘reporting this, hassling me’ .
1998		I. Welsh Filth 286: That creep that’s hassling her, what does he sound like?
2000		N. Griffiths Grits 66: It wuz when a wuz in-a army [...] asslin-a Micks like, bashin-a Paddies.
2002		Simon & Burns ‘The Detail’ Wire ser. 1 ep. 2 [TV script] You hasslin’ me about that shit? [e.g. a murder] .
2005		L. Redhead Rubdown [ebook] He’d been a terrible customer. Always groping, hassling for extras.
2010		Codella and Bennett Alphaville (2011) 30: We make every possible collar we can. We terrorize customers, hassle the dealing crews.
2016		D. Whish-Wilson Old Scores [ebook] ‘Hassling me cos’ I haven’t started’.
2021		J. Ellroy Widespread Panic 12: A jug-eared cat was hassling a boss blonde.
2021		P. Papathanasiou Stoning 35: ‘You can’t hassle people on a Sunday’.

2. (US) to quarrel.

1953		AS XXVIII:2 143: Present-day hassle (hassel) refers basically to struggle of some kind – a quarrel, tussle, mild disagreement, confusion, or disturbance.
1961		Rigney & Smith Real Bohemia 166: We had been hasseling for days.
1968		‘Sl. of Watts’ in Current Sl. III:2 29: Hassle, v. To fight, to challenge or bother someone.
1979		E. Torres After Hours 44: I never hassle over stray snatch.

In phrases

hassle with (v.) (also hassle out)(US)

1. to sort something out through discussion, to argue.

1967–8		Baker et al. CUSS 134: Hassle it out. Work out of a difficult situation.
1978		W. Wharton Birdy 99: While we’re hassling this out, we haul the wings and the bike back.
1984		C. White Life and Times of Little Richard 88: I always demanded to go on last. I’d hassle with some of these singers who had been stars for a long time.

2. to worry about, to be bothered with.

1953		AS XXVIII:2 143: [heading] Hassling with ‘Hassle’.
1972		Eble Campus Sl. Oct. 3: hassle – to cope with something troublesome.