Social challenges, in the Sims, are not my favorite kind. I tend to actually stay away from at least the Popularity Aspirations for that reason XD so this one was a tough one for me. Like ClayMask, it took me a couple of days to actually do this one. The other thing that bothered me was just the fact that Tony kept throwing up whims to marry the first two women he chose. So I kept feeling bad when I cancelled the interaction XD
Now, I actually kept him with only women, mostly because I tried to give myself something fun to do with this challenge and that was to have him try for baby with each of his women. But the first day, I had him go to the park and most of the community lots, just meeting as many women as he could so I could record them and so they were available in his relationship panel to be called up when it was there turn. It didn't matter if they were married or not, either. He wooed anything female. I think the one area I went wrong on is that i spent too much time with each woman. That and I really should have had him woo both genders.
Though one thing that helped where I didn't have to worry about having to do call-backs was getting them up to soulmates as much as possible. So even when they decayed, they didn't go below lovebirds.
Heh, as a note, Tony had 32 children with his 20 different women.