What should have happened
Tommy should have hit it with Amber, and then dogged her on national television stating that she was too big of a bi#%^ and he was just using her for sex. Then he should have hit it with Tara. Then he should have hit it with his partner Amanda after they won the 250k, because you know she was in a giving mood at that point, and she already felt comfortable with him.
Tommy should also hit it with Jillian cause she was the hottest beauty. In fact, Tommy should have tried to hit it with all the beauties from the show, except Randy cause she was ugly.
He should have hooked up with Leticia though, because she's older, more mature, and still hot. She probably would have made the best girlfriend.