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I think you have to sense if the girl is doing it to downplay the date. For example, “Hey, let’s go out”. OK! <later….> Oh, Anna’s coming along too.

That’s as good as a blowoff, and I dont’ like those dynamics because I feel like I’ve been half shot down already.

IN the poster’s case here, she pretty much came back out of the blue to invite him out with her friend. It’s not a strong overture, but it’s an overture. Reason I agreed that it might make sense is to skip it is for the same reason–the ‘we’re all friends’ dynamic can get in the way of what you really want. You can always meet the girl again a bit later.

As for the safety thing, I’d agree with Ryan in general–most women ‘get’ the dating scene, and it’s about meeting a guy. If you’re worried, you can meet at a public place. People who bring people along to protect themselves are quite likely people that you might want to avoid–that often comes from a pretty deep mistrust of guys–or from simply not being that interested.

That said, I was interested in a friend of mine and somehow she always ended up bringing her sister along until the 4th time hanging out, which was actually more of a date. That whole situation was odd though–and I never understood it.