Nechomah – I’ve never done it myself, and I don’t even know if I know anyone who has done it. But I have heard of it. I know many people are against it for the reasons you stated, but I guess as CTL and WTP said, some people feel it’s necessary. I can hear both sides. I think it really depends on the person and the situation.
Funny true story: A friend of mine agreed to go out with a certain boy. He called her at work (this was in pre-cell phone days) to set up a date for Sunday. Later that night (or maybe it was the next day), the phone rings in her apartment, and she picks it up, and it’s the same guy calling to set up a date with her roommate for Monday. She is like, “Do you know who you are talking to? This is _____.” She said he cracked up. She told him that she and her roommate would discuss it and decide which one should go out with him. They discussed it and came to the conclusion that he made the most sense for their third roommate. L’maaseh, they decided that the second girl should go out with him first. Neither of them ended up marrying him.
Moral of the story: If you do decide to go out with 2 girls simultaneously, make sure they are not roommates, and pay attention to the phone number you are calling!