When entering into a new relationship, there are plenty of hurdles to overcome. Getting to know a perfect stranger can lead to frightening revelations. The burning question for most men is, how much do you really want to know about your new lady and her sexual history? Before you answer, consider the consequences of finding out too much, too fast. Knowledge is power, and if you find out her dirty little secrets, the results could be disastrous. Learning about her first time, how many partners she has had or what she has tried can be pretty intimidating for a guy -- especially if you are a tad behind in those exploits.

Here’s the problem: Even if you decide (and it’s a wise decision) not to ask or know about her past, she may not have the same plan in mind for you. Chances are that she’ll tell you a thing or two as she gets to know and trust you. You need to consider why you don’t want to know about her past, and what to do when she tells you anyway. We’ll start with the former.
why you don’t need to know
You may think that you want to know about her past. It’s likely you think it will better arm you for the future -- that knowing will teach you what to expect from her. What you don’t realize is that knowing about her past can lead to awkward situations: you may make assumptions about her that you shouldn’t, you may freak out about what you learn and worry too much to enjoy your relationship, and you may even make jokes or comments about her past when you clearly shouldn’t.

The past is better left untouched. You will learn about her step by step through your experiences with her, and thus you’ll be learning together. When it comes to her sexual past, don’t recognize she has one: Live in the now.
Don’t ask too much
Keep in mind that as much as you want to know about her past, she may not want to tell you -- at least not right away. If you do decide to ask one or two sensitive questions, be sure to put your feelers out first. If she pulls back, gets scared or is put out by your questions, stop asking them. It may simply be too soon for her to trust you. She likely knows about sensitive male egos, and is not sure how you’ll receive the information. Her reluctance is probably for your own good.
Be careful what you ask
Asking too much about past relationships (numbers of partners, reasons for past breakups, etc.) can make you seem insecure and nosy. She may begin to think that you’re controlling or jealous. And in fact, knowing about her past may make you controlling or jealous, even if you don't mean to be. What if you found out she, in her capricious youth, cheated on a boyfriend and that ultimately caused the breakup? You’d be a lot more careful in trusting her, even if she’d learned her lesson. A few facts here or there can put you ahead of the game, but remember her past relationships do not dictate your current one.

why she may tell you
Once you’ve decided what you do and don’t want to know, she may mess up your plan by telling you things you didn't ask about. There are a few reasons she may do this:
It’s no big deal
The things she has done, she decided to do. It’s no surprise to her and she thinks you’ll be open to it. If it didn't bother her at the time, then why should it bother you now?
She’s looking to make you jealous
If you don’t make your feelings for a woman clear, she may decide to find out by testing you. Telling you naughty bits of her past might generate a reaction. Don't let her rile you with her manipulation. Make sure you're prepared for this tactic and see it for what it is. Women can be quite coy when it comes to relationships, so make sure you play it cool and don't fight fire with fire and think making her jealous will rectify the situation.
She wants to see what you’re into
It’s easy to gauge reaction when revealing sexual pasts. If your reaction is good, she’ll know how far she can go. Revealing a sexual past doesn't just mean how many partners and how often, it's also about experiences, fetishes, turn-ons, and everything that goes on behind closed bedroom doors. So, when she shares all her wild sexual adventures, she might be testing you to see how far she can go with you in the future.
She’s trying to find out about your past
She's thinking of the old game, “I’ll show you mine if you show me yours.” She thinks that if she tells a secret, you’ll feel secure enough or obligated to tell one too. Now, while you may not want to exchange tit for tat, so to speak, don't hold back entirely. This could end badly for you as she'll feel as if she has divulged her entire history to you and you've given her absolutely nothing in return. Relationships are about give and take, remember that.
She’s trying to tell you if she liked it
Certain sexual activities may have gone over well for her, while others may have been a bit stale. By telling you about the good and the bad, she’s trying to let you know before you try them  -- but she's not sure how else to bring it up. Talking about sexual experiences over coffee makes difficult subjects much easier to breach than if you were between the sheets.
She wants to boost your confidence
Reminiscing about her past allows her to compare what she has been through to what you're going through right now. If you’re doing well, maybe she’s trying to tell you so. Don't be offended by her tidbits of sexual exploits, just let her share and see where it goes and what she's trying to tell you.
She’s warning you
Some sexual pasts aren't as bright and cheery as others. Bad experiences happen and by her revealing some of the not-so-pleasant times she may be trying to let you in on a secret so she doesn’t catch you by surprise. If you think a blatant admission is shocking, imagine if you'd found out on the fly?

how to handle her past
Now that you’ve learned things, either because you asked or because she blurted it out, you need to decide how you’re going to handle the situation and the information. A gentleman will take it in stride and deal with it maturely. Here’s how to keep things in perspective:
Think about your past
When you start to get worried about what she’s done (or who she’s done), think back to all the encounters you’ve had. You didn't always act with class and dignity, and chances are she hasn’t either. Try to use the same standard for yourself as you set for her.
Disassociate present from past
Just because she once made questionable decisions, doesn’t mean she does so now. Get to know this girl for who she is, not who she was way back when she was a different person with different interests. Don’t let it cloud your view of her now.
Try something new
Decide on something you’ve both never done, and give it a try. Since you’ll both be learning and growing together, you’ll make a new bond, and be forced to think currently. And also keep in mind, just because she's done something in the past, doesn't mean she won't want to do it again.
Know your limits
If you do decide that you can’t handle what she has told you, just get out. The further you get into a relationship the more you’ll drive yourself crazy, and likely her as well. The longer you wait to make the break, the more it will hurt. Don’t wait, because if something bothers you now it’s likely to get worse as your attachment to her gets stronger, not vice versa.
opening pandora's box
All in all, it’s best to leave the past in the past. You’re better off thinking of yourself as the first (although obviously you should protect yourself as though you’re the hundredth) so that you aren’t intimidated or put off. But if, for whatever reason, you find out about what she has done, be decisive about how you’ll handle it and always be a gentleman about it. Remember, you have a past too.