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If you take her to a place she likes, you get sappy music and a happy cutscene. If not, you get Rage Against the Machine and a failed date.
There are six girls found around the map that are dateable.Consider flying your date in an airplane or helicopter if her location makes this feasible. They will be VERY appreciative, even if you are barely able to land (at least with the "Hot Coffee" mod which may have unlocked some additional uncensored materials). If you take Millie for a driving date in a helicopter she will quickly get upset about the speed and the date will end soon.Do this after you complete the mission learning to fly.If she's not home the red marker and car won't be there, and if CJ tries to visit anyway a text message will tell him she's not home.Upon entering the marker, one of several types of dates is chosen randomly and the girl will tell CJ where to take her.
Take her to a fast food joint, bar, diner or restaurant (some of these may not show up on your map until you start the date).