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.
by Soubriquet11 April 16, 2024
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Non-Ugly

Being NOT ugly
"Wow Joe, Judy is non-ugly today."
by Jayden Michaels July 29, 2018
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ugly o clock

The time when events go south at a bar or series of bars close to each other(Caroline Street in Saratoga Springs on a Friday or Saturday night) A time when fights break out, people get thrown through windows stabbings and even people getting shot. The timing is fluid, it can start anywhere between 11pm to 4am and happen multiple times despite a large police presence.
Hey, let's get out of here, ugly o clock has just started and I don't feel like dealing with some chode who going to try to pick a fight with me.
by GrouchoMarxx April 29, 2022
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