DeVontray is an 18 year old division 1 basketball player who gets a serial date with 5 guys Billy 21 Matthew 21 Greg 24 Robbie 20 Jerry 23 DeVontray's date starts with some one on one court time followed by ice cream and a walk on the boardwalk. In the second segment Nick is a 21 year old recording engineer who dates Michelle 23 Kara 20 Mackenzie 20 Brittany 20 Aubrey 20 Nick starts his date with some juggling and busking followed by some "date painting".