19 year old Vanessa is set up with 5 dates Seth 18 Dylan 20 Taylor 20 Dustin 18 John 19 Vanessa's date starts with skydiving after asking the guy to pack his own chute. That's followed by the jump itself and then relaxing in an inflateable pool. 21 year old AIr Force trained Brett has dates lined up with Jessica 18 Vanessa 20 Monica 22 Lacey 18 Holley 19 Brett's date starts with rock climbing followed by a trip to the beach.