What I keep running up against is that while I can do a pretty good job arguing for remaining a virgin until marriage, I have no clue what a person who isn’t should say if they repent of their past and want to make a go at a chaste courtship.
So, as a young Christian man looking to find a wife, I’ll answer.
For any woman considering lying about how many men she slept with, the answer is always don’t (at least if you plan to have the relationship be long-term; if it’s a simple fling, it probably doesn’t matter).
I can not stress how important it is for women not to lie, dissemble, avoid answering, or otherwise conceal the truth about how many men they slept with prior to a partner they hope to be in a long-term relationship or marriage with.
A relationship built on a lie is not healthy. The truth will eventually come out (one of your friends will eventually accidentally mention Steve) and when it does, the consequences for lying will be what the consequences for lying usually are.
As for avoidant answers: any man with any self-respect and options who hears “it’s in the past”, “it’s none of your business”, “it doesn’t matter, I’m with you now”, etc. will consign you to the short-term, pump n’ dump, or just plain dump categories.
So, the question then becomes how should a woman inform a man she’s considering a long-term relationship with that she’s slept with many other men?
First, realize that he likes you. If he’s dating you and a long-term relationship is a realistic possibility, he is very favourably disposed towards you (or exceedingly desperate, but we’ll ignore that). A man in love with a women will look on anything she tells him in the best possible light; the haze of infatuation can cover many more sins than you possibly realize. If you address the issue properly, odds are it will cause some troubles (as sins do) but won’t end the relationship. If it would end the relationship, it is far better for it to occur now than during the engagement or after five years of marriage.
Don’t be afraid of telling him.
Second, don’t bring it up first. There’s no need to. If he asks, tell him, but some men honestly don’t care. If he doesn’t bring it up, there’s no need for you to go out of your way to volunteer the information apropos of nothing. If he doesn’t bring it up, and only if he doesn’t bring it up, he might simply prefer not to know or not care. If he doesn’t, don’t worry about it. If he does ask or even mention its, he definitely cares, so definitely tell him.
Third, be honest. Honesty is by far the most important thing. Do not lie, do not be evasive, don’t “be cute”, don’t underestimate, don’t exclude those times that ‘don’t count’, don’t conceal anything, etc. Tell the full and honest truth. Also, yes, oral sex and anal sex do count, as does sex that ‘didn’t mean anything’, one night stands, sex in foreign countries, and ‘just that one time in high school’. If it comes to mind, it counts.
Fourth, the exact number probably doesn’t matter, but do not lie about the number or give a false impression. Whether it was 6 or 8 likely won’t matter, whether if was 14 or 18 won’t matter. Unless he asks for a specific number, once it’s over five or so, the specific number if not really of importance, the range is. If it’s under five, just tell him the straight number. ‘Many’ is a legitimate answer for anything over 5 (‘a few’ is not; a few means less than five), but will likely prompt calls for clarification. ‘High single digits’ or the exact number works for anything under 10. ‘About a dozen’ is a legitimate answer for anything from 10-15. ‘About 20’ will work for any number from 15-23. ‘A few dozen’ will work for anything over 24, but under 50. ‘Over 50’ or ‘over 100’ (really?) is sufficient for anything beyond that. You do not have to be specific, unless he asks for specifics, but you have to be truthful. If you would honestly use the descriptor in everyday life for the accurate measurement of the quantity of mundane things, then it’s fine to use as a descriptor here.
Fifth, realize exactly how important this issue is. You may try to delude yourself that it doesn’t matter, that it’s a small thing, etc. Many crooked souls and diseased minds will tell you the same. Do not listen to them. It matters.
If you’re a Christian, reading Deuteronomy 22 should be more than enough information on how important God views this issue as. Fornication is a sin against God, against yourself, and against your future spouse. Do not belittle exactly how sinful it is. All sin has worldly consequences; fornication is not an exception. There will be earthly consequences for violating God’s law.
If you are a non-Christian, know that the single biggest risk factor a woman has for divorce is the number of sexual partners she had prior to marriage. Having one premarital partner doubles the risk of divorce, two partners triples it. Sex has immensely strong neuro-chemical effects that bond you with sexual partners; the more you have bonded with, the less bonding will occur with further partners.
Whatever hedonists and libertines may tell you, having numerous sexual partners seriously hurts people’s abilities to bond with intimate partners. Your numbers prior to your current partner do matter. Do not take it less seriously than it deserves.
The amount of men you’ve had sex with does matter to your partner, it is his business, and he’s not being a judgmental asshole by asking. (The same goes for vice versa; men, if your long-term girl asks, answer truthfully). Trying to shame him into not inquiring as a short-sighted thing to do.
Sixth, be genuinely repentant. This matters a lot. Once you realize the gravity of your previous sinful actions, repentance should be your desire. You should be genuinely repentant and sorrowful that you have harmed your marriage through your actions prior to marriage and it should show through in both word and deed. There should be no pride, no excuses, no indignation that he would ask, no accusations of judgmentalism, no “born-again virgin” nonsense, etc. Simply ask his forgiveness. You should display be nothing but authentic remorse and humility for misguided actions. If you don’t feel genuine remorse and aren’t truly repentant, than you don’t understand the gravity of your prior actions. Read your Bible, particularly those sections on sexual sin, more and/or truly try to understand the statistics linked above until you do; you are not ready for marriage until you truly understand this.
Seventh, do not bring up prior partners with him outside of this specific discussion. Never compare him in bed to anyone else. Never talk wistfully about past partners. Never idly wonder out-loud about past partners. Don’t have any keepsakes. Etcetera, etcetera. It’s simple, never bring up anything that has to do with previous sex partners.
(The widow is an obvious exception. It is fine to keep some momentos of a dead spouse and to occasionally mention him, but still avoid comparisons. The other exception is in a serious, humble talk with other women, to show them the error of licentious living.)
Eighth, have no expectations or demands. You do not ‘deserve’ to have him marry you (and he does not ‘deserve’ you). Just because he forgives you, because God’s forgives you, does not mean that there are no consequences. He is completely justified in breaking it off for your past actions. Do not guilt him for his reaction, do not demand he remain yours, do not pressure him, do not question his manhood, etc. Simply be humble, ask his forgiveness, await his answer, and accept his decision.
That’s it. In a nutshell, be honest, be repentant, be discreet, and recognize your actions for what they truly are.
Realize that there will be earthly consequences. He might break-up with you, you will hurt him, you will be hurt yourself, there may be long-term distrust or other long-term issues. The earthly consequences of sin do not disappear simply because you are forgiven by God, or even if you are forgiven by man.
Of course, all this can be avoided by being chaste, that’s by far the better option if you ever want to marry.