‘play the field “avoid commitment” (1936) is from notion of gamblers betting on other horses than the favorite”

http://www.etymonline.com/index.php?term=field

But what is that all about?? The idea is that the gambler is not sure which will be the winning horse, so rather than betting on ONE horse (compare committing to one woman), bets on SEVERAL horses in the same field (race).

Compare:

http://www.askmen.com/fashion/austin_100/138b_fashion_style.html

Butterfly’s answer makes the most sense and is most in keeping with what I understood the origin of the expression to be. Don’t just bet on the favorite horse — spread your bets around (i.e. play the field) — something like ‘not putting all your eggs in one basket’ or keeping all your options open.

I had actually thought it was to do with soccer — don’t always pass the ball to just one team mate, but ‘play the field’ — share the ball with all your team — all over the field — to give everyone an opportunity to play and score.

Anyway, whichever of these two is the correct origin of the expression (and I suspect it’s hers) everyone who answered was right about what it is now used to mean: Not dating just one person; instead, spreading yourself around. In other words, a person who likes to ‘play the field’ isn’t ready to settle down to a monogamous relationship!

You’re freer to roam when you “play the field”.

if girl or boy friend tell you still wants to playing the field that means she or he wants to see other people beside you until she or he finds the right guy or girl its sound kind of bad but hey **** happen