You tryin to go out?
Used by teenage boys in highschool to "flirt" with a good looking girl in class but can be also used as a joke said to a girl who the person thinks is not goodlooking
Brian: Heyy
Kylie:hi
Brian: You tryin to go out?
Kylie: whatever
Kylie:hi
Brian: You tryin to go out?
Kylie: whatever