To Or Not To??

As you know, I've been a lonely sad sack for quite awhile now. It's during these times of drought that misplaced thoughts and bad ideas tend to creep up with more frequency. Case in point: Should you ever date friends?

I know all the magazines talk about the importance of friendship first and don't discount what's right in front of you; but I have to wonder: Is that really a good thing?
[side note: I totally felt like Carrie Bradshaw writing that last bit! God, what a nerd.]

I established the No Friends Rule after my ex became best friends with many of my friends while we were going out and then refused to give them up after we had broken up. It was awkward for quite a long time to say the least. I hoped to avoid this in the future so I said, "No more dating friends and no more introducing dates to friends". Surprisingly, this rule stayed intact for quite a few years. I never felt tempted to break it or emend it until a couple years ago. The addition to the rule was simple: You can date friends if they're not your best/good friend and/or are not best friends with your best/good friend. This allowed me to entertain the notion of acquaintances and casual friends without feeling bad or worrying about the consequences. It worked really well and I felt freer to accept what happened naturally. It also forced me to be more honest in the way I treated these relationships. If I wasn't feeling it, I had to nip it in the bud immediately or risk losing that friendship.

Now, I have to reflect on this rule again. You see, it would be easy if I met people outside of the group but you know my "stranger danger" mentality doesn't bode well for that. The other option is to encourage my friends to get attractive new friend's and invite them over more. (Why can't that work??) Otherwise, I feel I will soon be forced to address this situation head on and either make a concession or stick to my guns. Either way could end poorly.

I feel I would be remiss to deny an opportunity to have a little fun (and maybe cause my eye to stop twitching for an evening- PLEASE!) and explore; but, how do I know if I should? Is there a checklist somewhere I could use? You know how much I love lists! Is there anything that's a deal breaker? I know what kills it for me in a relationship but have no real idea what makes for a good person to date. You'd think with very little standards I'd have more offers and dates coming in! Usually I think 3 things when evaluating the situation: Are they cute/am I attracted? Do they fit the preexisting list of all potential mates (They must be my height or taller and they must be my age or older)? Do we have anything in common?

Is that enough when your treading on a friendship?

Maybe I'm over thinking and whole possible future situation is in my head. Even so, surely I must be prepared if and when it does come up. Help!