Jada Pinkett and 2Pac go back.  According to the now-Smith, she met Pac when she was dealing drugs and the two held each other down, but never had a romantic relationship.

Will Smith did the Breakfast Club this morning, and they asked the superstar if he was ever jealous of the relationship Jada and Pac had.

"Oh, f yeah ... That was in the early days.  And that was my biggest regret.  I could never open up to interact with Pac. Cause we had a little bit of a thing. Because, you know, they grew up together and they loved each other. But they never had that sexual relationship. But they had come into the age that now that was a possibility and Jada was with me. ... But she just loved him, like he was the image of perfection.  But she was with the Fresh Prince. [Me and Pac] were in the room together a couple of times, I couldn't speak to him ...  I couldn't handle it. I was the soft rapper from Philly and he was Pac."

Pac seemed to have a certain effect on women. Lisa "Left Eye" Lopes was similarly attached to Pac, and although that relationship was also said to be platonic, it helped to ruin Lopes's romantic relationship with Andre Rison.

Luckily for Smith, he was ultimately able to overcome his jealousy and now we are blessed with Jaden.