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Are you on a controller or mouse and keyboard? If controller I might suggest turning up sensitivity on it so you can move quicker for that part.
1. After talking to Vickie and Ashley and deciding that Derek should be "the one", wait until Derek is not in the vicinity of Madison. Ideally Madison would sit in the gazebo while Derek is somewhere in the house. Save the game, then talk to Derek.
2. After your conversation with Derek, Ashley and Vickie will start moving. You can actually follow them around to see where they go and if they both find the way into the closet. Derek will go to Madison, but the plot will not advance until you're in their vicinity to hear them talking.
3. Go outside, but stay as close to the sliding glass door as you can. Tiptoe forward until you trigger the conversation between Derek and Madison. As soon as it ends, run into Madison's bedroom. Ashley and Vickie should both be inside the closet at that point. Open the left closet door to get in, then close both doors.
If it doesn't work, reload the save from step (1) and try again. You may need several attempts. Don't try to load a save from a point after step (1), because then you may run into a situation where the pathfinding gets disrupted and Vickie doesn't find the way into the closet. Depending on when you save and where Ashley or Vickie are at that point, it's even possible to have Derek enter the bedroom before the girls arrive there.
Looking back at this, they did slightly change a few things on this part that I recall (though minor if so). Says to eavesdrop Madi and Derek while they talk by the gazebo, then says to quickly run upstairs to master bedroom, approach Ashley (recommend skipping the convo quick to end it fast), get in closet and close the doors.
The conversation for Madison and Derek going to the bedroom won't start until you get close to them, so make sure Ashley and Vickie are in the closet before you activate that conversation.