Green’s Dictionary of Slang

1. (also cutiepatootie) an attractive woman, usu. young, poss. a man’s girlfriend; also attrib.

1922		Burlington Free Press (VT) 29 Nov. 5/4: Bobbed-haired young women using the mails for their ‘cutie-pie’ correspondence.
1937		St Louis Post-Dispatch 16 Feb. 3D/3: ‘The Women’ [...] has set husband against wife, boy-friend against cutie-pie.
1947		Dixie Dugan 18 Sept. [synd. comic] And don’t start calling me ‘kitten,’ ‘cutie-pie,’ ‘baby’ [...] or any pet names after we’re married.
1948		J.M. Cain Moth (1950) 17: The cutie pies got eighty cents a Sunday for doing it.
1952		(con. 1920s) ‘Harry Grey’ Hoods (1953) 252: Hello, cutie pie.
1963		T. Southern ‘Twirling at Ole Miss’ Red Dirt Marijuana (1973) 136: Most of these girls come every year — I talked to one from Honey Pass, Arkansas, a real cutie pie.
1972		Hall & Adelman Gentleman of Leisure 18: Myself – I like cutie-pies – attractive young girls.
1979		Orlando Sentinel (FL) 8 Aug. Hey there cutie pie! What’s shaking?:
2000		Eble Campus Sl. Spring 3: cutiepatootie – attractive member of the opposite sex.
2000		P. Beatty Tuff 149: He could slide up behind a cutie-pie, align his zipper with the groove in her behind, and ride her ass until he needed a beer.
2007		UGK ‘Int’l Player’s Anthem’ 🎵 So I typed a text to this girl I used to see / Sayin’ that I chose this cutie pie with whom I wanna be.

2. a man, as a term of affection or ridicule.

1952		(con. 1920s) ‘Harry Grey’ Hoods (1953) 108: Noodles, you cutie pie.
1981		H. Gould Fort Apache, The Bronx 180: Why didn’t you drop a dime on him yourself, cutie pie?
2010		L. Berney Gutshot Straight [ebook] ‘Senora Boxman,’ he said nervously. ‘Good afternoon, cutie-pie’.
2015		L. Berney Long & Faraway Gone [ebook] ‘Her kid’s a cutie-pie, according to my wife’.

3. a small, admirable object, esp. used ironically.

1993

S. King Dolores Claiborne 4: Don’t these Japanese just make the most cunning little things? [...] I guess we both know what’s going on the tape inside that little cutie-pie could put me in Women’s Correctional for the rest of my life.

4. a child.

1991

C. Hiaasen Native Tongue 294: What, you got something against little children? Little cutey pies having a good time?

5. (gay) an attractive, feminine man.

2002		‘Rev. of Total Corruption’ HisXpress.com 🌐 Ross and cutiepie Baldwin finish the video with Baldwin playing a sleeping bottom.
2003		K. Cage Gayle 64/2: cutie pie n. attractive young man.