“Wine, dine and sixty-nine”

“Wine, dine and sixty-nine” (also “Wine me, dine me, sixty-nine me”) is one version of date. The slang term “sixty-nine” (69) is a sexual position. “Wine me, Dine me, 69 me” has been cited in print since at least 1991, when the saying was printed on T-shirts.
 
“Wine, dine and pocket-line” is a related saying.
 
     
Google Books
Around the Spanish Main:
Travels in the Caribbean and the Guianas

By Hugh O’Shaughnessy
London: Century
1991
Pg. 70:
‘Wine me, Dine me, 69 me,’ say the T-shirts hung out to catch the tourist eye along Front Street in Philipsburg, the capital of Sint Maarten.
   
Alanis Morisette Lyrics
“Right Through You” (1995)
(...)
You took me for a joke
You took me for a child
You took a long hard look at my ass
And then played golf for a while
Your shake is like a fish
You pat me on the head
You took me out to wine dine 69 me
But didn’t hear a damn word I said
 
OCLC WorldCat record
Wine, dine and 69 ways to get some : a locker room guide to scoring with the beautiful women of the world
Author: J B Lane
Publisher: Victoria, B.C. : Trafford Pub., ©2003.
Edition/Format:   Book : English
 
Google Books
Go, Girl, Go!:
The Women’s Revolution in Music

By James Dickerson
New York, NY: Schirmer Trade Books
2005
Pg. 150:
Then in “Right Through You,” she sings: “You took me out to wine dine sixty-nine me/But didn’t hear a damn word I said.”
 
Google Books
Memphis Underground
By Stewart Home
London: Snowbooks
2007
Pg. 33:
“Well, I’m sure there are lots of people in the office you could go to lunch with, there’s Colin from Marketing, he’s always looking for people to wine, dine and sixty-nine.”
 
Google Books
Cook to Bang:
The Lay Cook’s Guide to Getting Laid

By Spencer Walker
New York, NY: St. Martin’s Press
2010
Pg. 2:
Learn how to wine, dine, and sixty-nine your dream date with minimal harm to your credit card or self-esteem.
 
Twitter
*cherry pop stand*
‏@gingerbeerkiss
What ever happened to the old saying
Wine, dine & sixty-nine
What ever happened to doing those things
5:35 PM - 29 Jul 2014