Dawn falls for and starts dating Chris's old friend, Jack from his former prep school and she tells Cassidy that he might be the one. Chris finds out that Jack is still with his old girlfriend and Cassidy tries to tell Dawn, but she doesn't believe her. Dawn confronts Jack who tells her that it is over between him and his old girlfriend, but later finds out that she had been lied to. El-Train hits the road with Al and Jamal in his fixed up van to go attend a DMX concert. On the way, they pick up a hitchhiker who robs them and leaves the three tied up on the side of the road.