To seriously answer the OP's original question, I think whether a girls sexual history matters depends on the man, just as a man's sexual history matters to some girls.
To someone who believes in waiting until marriage to have sex, it is probably important that their partner has similar beliefs and has acted accordingly.
To someone who is jealous and insecure, a partner with a colorful sexual history may exerbate the issue.
To someone who believes in monogamy, it matters if the other person has shown a history of cheating because chances are good it will be repeated.
To someone who wants to be adventurous and kinky, it may be a good idea to hook up with someone who has an adventurous, kinky history :p .
Someone who wants a one night stand should connect with a partner who wants the same thing.
Of course there are always exceptions, so the playboy may, in fact, have a wonderful, lasting relationship with an inexperienced virgin.
I think the key is to get to know your potential partner and find out what his/her beliefs are about men/women and sexuality as well as a little about their own history before jumping in to bed with them.
I do happen to agree that having multiple relationships (monogamous or not) can affect one's ability to bond
with the same innocence as the we did the first time. Before I get run out of the Cellar on a rail for agreeing with Bmwcmaw, let me explain. Breakups and hurts caused by relationships gone bad become baggage that we carry with us. We are much less likely to throw ourselves 110% into subsequent relationships and to trust unquestioningly when we have had failed relationships in our past. We learn to be cautious and safeguard our well being.
I loved my first partner and husband (yes I waited to have sex until marriage)
deeply and passionately. Huge red flags and clues that he was abusive and a cheater were totally ignored in the blindness of first love. I didn't recognize them because I'd never seen them before. Now I know better. No one will ever again get that pure, absolute, and total submission of my heart and soul. Of course, my current partner gets a much wiser, emotionally healthy and independant woman than I was way back then.
One last thing...I don't think its the 'chase' thats important, its the 'anticipation' that is so much fun. Putting some time between meeting and actually sleeping together lets the sexual tension ratchet up which tends to cause the eventual conclusion to be worth the wait.
Stormie