Listen up, Ladies!
It's hard to make friends, especially when you're older. A teacher I had in high school once told me that people really only have one or two real friends their entire lives. At the time, I found that hard to believe, and still don't completely buy into such a small number of people, but I'm starting to get it. People who are truly there for you, and for whom you are truly there shouldn't be too large of a number. Like anything else spread so thinly, platonic love, too, will eventually dissipate. So, if he's got a lot of friends, too many friends, this could possibly be a Red Flag.

And how does a myriad friends turn into a Red Flag?

1) What kind of friends are they? If he grew up with many of them, went to school with them, or shared any kind of formative experiences with them, that is more understandable. However, if he met them all in bars, casinos or tailgating football games, this may be a sign that he takes closeness too lightly. Having fun with people is good, but when he calls the stranger who gave him a Pabst Blue Ribbon outside the football stadium a buddy, he probably doesn't know what close is. What's more, he probably can't get that pseudo-collegial feeling without a big event and some beer. Your real affection may not be enough.

2) Who is he to his friends? It is more common, and, apparently, more healthy, to have some friends that are closer than others. However, if he is the same guy to all of his friends, this may say something about the genuineness or his connections (or his character, itself). Basically, there are two general ways to be the same person to all your friends (you either care too much or too little). The person who has to take care of everyone or be there for everyone definitely doesn't have the time, or desire, to make you his main squeeze. The other kind of person is more like a sitcom character who pops in for good times and leaves when he needs to, who is always the same person with the same issues. If you don't mind dating Cramer from Seinfeld, this person may be the one for you. However, if you want something a little deeper, you're not going to get it from everyone's novelty act.

I believe that a guy who has friends is imperative to a fulfilling relationship. However, I believe there is a certain amount of friends that is healthy and manageable. I can't give you an exact number, but I know it when I see it. Do you?
 

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Would you date someone who had previously dated one of your friends?

Yes! I'm perfectly happy to date my friend's exes. They're exes for a reason.

No! It's too incestuous. I don't feel comfortable dating a friend's ex.

Maybe Yes: I haven't had the opportunity, but I don't see a problem with it.

Maybe No: I haven't done it, but I don't think I would.