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To fill Chastity's (or any other stripper's) like meter, one must get a private dance with her and flirt/touch her until the like meter is filled. Players should be aware, however, that there is a guard who constantly walks around for a few seconds and comes back; if this guard sees the player touching her three times, they will be thrown out of the club (this does not apply to GTA Online, or in single player after completing the mission Hang Ten). GTA Online players must use their microphone to flirt with the stripper.
In GTA V, once her like meter is filled, she won't be available to take home. This is due to the fact that Chastity does not sleep around. Nevertheless, in GTA Online, after she gets her like meter filled, the player will get her phone number and is able to invite her to his/her apartment and do lap dances for free in their place. In her lap dances, the stripper will get mad and leave the player when it looks like she's being ignored.
There is an unused, yet working phone number in the game's files that corresponds to her, meaning that the player was supposed to take her home during story mode. The same applies to the other girls who cannot normally be taken home. The number is fully functional, but as no dialogue was recorded for the scenes, they will be silent.
Gallery
Chastity performing her pole dancing routine.
Posing for the guests.
Trivia
Chastity is the term for being sexually abstinent, also reflected in the fact that she cannot be taken home.
She also points out how she named herself Chastity and that she is aware of the irony behind her name.
While getting a dance from Chastity, she will sometimes point that:
She hates stripping but would rather strip than be broke.
She used to be blonde and that blondes are dumb.
She painted her hair dark after she became a goth.
She shares a character model with Fufu, the differences being the clothing styles and hair color.