Top Definition
A weekend in which a man dresses in women's clothing and assumes a female identity in order to determine whether or not he would enjoy being a woman. Inspired by the movie "Tootsie" starring Dustin Hoffman.

Not to be confused with a Doubtfire holiday in which a man dresses as a woman to secretly spend time with his children.
Brett: Hey, man! You wanna come over on Saturday and play "Call of Duty"?
Marty: No, thanks. I'm gonna do a Tootsie weekend.

Devin: Do you like mascara?
JJ: Yeah, I kinda do. I think I'm gonna do a Tootsie weekend.

Ryan: Hey, how was your Tootsie weekend?
Gus: Great. I think I'm gonna become a woman.
von Lil' Shammie 20. August 2013

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