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I don't think it's insane to be concerned about how many partners someone has had. Regardless of how "safe" your practices are, it increases the chances that you have caught something. Tests aren't 100% (and for all we know there are new diseases they don't catch). For that matter, I might not be 100% comfortable taking your word on the tests (people do lie sometimes).
That's not to say there is some magic number. But as the number goes northwards I would probably hesitate, were I dating right now.
Moreover, the more partners you've had, the smaller the chance that you and I will hook up permanently (after all, none of your other SO's lasted), so if I were looking for something permanent, I might well decide you weren't for me. Many guys would like to be special to their SO's, and it may be harder to have that feeling if you have had a ton of partners. (For that matter, your greater sexual sophistication alone is going to scare off plenty of guys.)
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