playing the field 

When a person dates numerous people but is in no serious relationships.

Michael was almost happy that his girlfriend broke up with him because he was looking forward to playing the field.

playing the field by Bruwres July 22, 2009

Playing the field 

When a person juggles multiple romantic relationships with different people at once. Playing the field involves the player actually going on dates and is actively engaging in the relationships instead of just hooking up (see thot or fuckbuddy)

As he moved to the city, he began playing the field with lots of women before getting caught

Playing the field by thelionking____ November 3, 2022

If there is grass on the playing field 

If the girl is old enough to have 'grass on the field' than she has reached puberty and has pubic hairs, making her 'game'.

"is your girl old enought?"
"Hey... if there is grass on the playing field, then play ball"

If there is grass on the playing field by bhgtbtbhtbhtnh July 26, 2006