Playin ugly, Playing ugly, playin ugly to me.

Playing ugly, means you are hitting on someone, trying to pick up. Most often in a bar setting, can also be a club or gig setting.

Playin ugly, Playing ugly, playin ugly to me. Playing ugly means: There is a person who is flirting with another person. Most commonly unwanted flirtations occurring in, most commonly a bar setting.

I'm sure he's Bill or Billy or Mac or Buddy
And he's playin ugly with me
And I wonder if he's a had a day of fun in his whole life.

This woman is playin' ugly to me an all I wanna do is bounce.

That jerk at the bar won't quit playing ugly with me and all I wanna do is have some fun with my gf's tonight.