I know Jennifer was mostly into rich older men (lets face it she was a golddiger), but I think if she were to settle for someone her own age I think she and Venus would have made a great couple. For starters they are both into fancy clothes and fashion, and probably would love nothing more than to shop together, and they both appreciate the finer things in life. Also they are probably the two smartest people on the show. Whenever anyone had a problem they went to either Jennifer or Venus.

Those are all good points. Other than Jennifer's stated preference for older, richer men, I can't think of a reason AGAINST them being good for each other.