You can’t shape the dating atmosphere to your advantage without anticipating what is likely to come up. This post is aimed at reinforcing the more practical side of a subject and admittedly aims more at younger than more mature women.
Perhaps the toughest test of your worth to Mr. Good Enough, can and will he accept you without knowing the details of your past sex life? He has four interests: to determine his comparative value as a lover, to prevent his embarrassment as your lover, to determine the likelihood of you cheating, and what really intrigues him: Promiscuous? With his friends? With someone he knows? Mistress? Shack up? Cheap? Easy?
It’s his nature; he’s born that way. Men begrudge anyone who went before them, and the begrudging varies with who are the individuals. Husbands can be forgotten as legitimate earners of your favors (unless you bring it up)—but not the others and some measure of too many or too much reflects harshly against not just you but more importantly him.
CAUTION: The Manosphere loudly broadcasts that women are equally entitled to sexual freedom and their history is of no concern to advocates of Game philosophy. Don’t fall for it, darling. Their philosophic values are founded on the supreme superiority of men over women to the extent that respect for women is non-existent. Their philosophic flavoring floats on Feminism, tends toward homoeroticism, and leans on Islamic values. Overall, it contradicts anyone’s interest in sexual discretion and monogamy.
Here are a dozen pointers to help shape the dating scene to your advantage.
- Your known past generates suspicions that override acceptances and assurances. Your unknown past generates fewer suspicions to eat away at the mutual trust you hope to build. 
- Men seek and others often advise full disclosure. When men actively pursue more about your past, they can’t ignore and not use the information to shape their thinking. Talked into full disclosure, women expect fairness and equality. The male nature does not originate fairness for sharing sexual assets, and equality is a female concept that men don’t normally consider in human relations. 
- People argue that trust cannot arise without full disclosure. Hah! Trust arises from convictions drawn from beliefs and speculation about a person. Trust does not arise when specific knowledge prevents such convictions. 
- Full disclosure comes out uneven, unequal, un-repairable, because the male nature values a woman’s chastity far more than the female nature finds interest in a man’s sexual history. 
- The harder a man works to draw details out of your sexual past, the more likely he will use it against you sometime, someway. Perhaps latently, indirectly, or vengefully. It’s available to hold over your head and to rationalize or recover from his own mistakes. 
- Forgetting your sexual past with lack of knowledge is far easier than forgiving what Mr. GoodEnough learns from full disclosure. The more he knows, the more he thinks. The more he thinks, the more he looks for the bad or unacceptable. The more unacceptable, the less forgetting. The less forgetting, the less forgiving. 
- Feminine intuition trumps full-disclosure. While not easy, you are blessed with the skills and expertise to withhold who, what, when, where, why, and how of what he doesn’t already know. Withholding information is not dishonesty. Disclosure means candid, accuracy means honest. 
- His spirit and willingness to give more than he takes may indicate his ability to honor your decision and help qualify him as Mr. GoodEnough. However, if he’s more of a taker, he may not honor your other expectations either. Such as these after marriage: Have kids even though he agreed. Or your desire to stay home and home school, when he wants more income in the home. Or support you in caring for a sick parent. 
- Your undisclosed sexual past defends your relationship, because his ammo box lacks your historical bullets to fire back in domestic squabbles. 
- The forward-thinking woman convinces all her female friends to never leak anything about her past to her dating partner, boyfriend, husband, or any other man. But this may fail too, because friends betray friends. They steal dates, boyfriends, lovers, and husbands, don’t they? Consequently, the wisest woman keeps her sexual history as secret as possible even from friends and family. 
- Former relationships may be known to your man, but no mention should be made or comparative details disclosed. It’s toxic in any relationship for you to disclose the relative sexual worth of one man to another, regardless of who’s the better. 
- Don’t think you can outsmart him by claiming he’s your greatest lover ever. You opened the door to his inquiry about how and why he’s the greatest, so you’re trapped into telling what you’re best off not to disclose.
The more that Mr. GoodEnough knows, the more likely he will make you pay some price for your past. Couples do squabble. You may never know or understand what’s happening. Yet, he may strike back because of your earlier sexual events. It takes very little for reminders of your past to grow into humiliation for him. Your history affects his sense of significance, whether you know it or not and accept it or not.
I know this subject has been perhaps overheated and difficult to accept. Too much of a good thing can still be boring. Tomorrow’s subject is also a tender one that needs to be reviewed for mid-life dating. It’s submission, even though we all know that subject doesn’t apply before marriage. Preparation is easier than recovery, which is the not just everything but quite often the only thing.