After the raid on the movie theatre, the males and females would not be held in the same holding cell, plus personal belongings, such as Bailey's purse, would have been confiscated while they were in custody to be returned to them upon their release.
Bailey Quarters challenges Herb to draw cards for her poker winnings (and an evening out with Jennifer) vs. Herb agreeing to go to the hospital for tests. Bailey cuts the deck first and announces that unfortunately, she drew a four. Herb draws and says "Just my luck, I can't even beat a four!" but never shows anyone his card. Later, we see the card Bailey drew still in her hand: it's actually a two of spades.