from a financial standpoint dating multiple people is costly. I used to date as many broads as I could thinking it would boost my ego which in turn would boost my self esteem. That didn't work. First, as I said it was expensive. Second, it was like a full time job. I couldn't hang out with my friends. It was also pretty hard hanging out with these women/girls because deep down I really wasn't that interested in them from a personality perspective. I liked having sex with them and I liked the fact that they liked me (how fucked up is that?). I would end up resenting them because I was sick of being with them, and then I'd be upset with myself for hanging out with women I didn't like, some of which were very annoying (but smokin' hot).
I did get some great stories to tell my buddies, and some great sex. But that was about it. My self esteem issues were still there, and I was getting broke, and wound up with some angry bitches because of how I went about dumping them.
It's more healthy to date someone you really like, IMO.