Six Truths for Dating Someone with a Sexual History

For some reason, the modern sitcom seems to be the only venue that openly addresses the dark awkwardness of a dating partner’s sexual past. Television can make such a history into a lot of things — meaningless, devastating, even humorous. But it cannot redeem it, at least not in any truly deep and lasting way. But the gospel offers real grace for the heart reeling that can happen from finding out about a boyfriend’s or girlfriend’s sexual past.


The one who has his or her own sexual history faces their own challenges. The twin emotions of dating someone with a sexual history, though, are insecurity and obsession. Insecurity, because you feel exposed and already judged when you feel the weight of your partner’s regret and struggle to process what their sins mean for you. Obsession, because you want to let the past be the past, but only after your own morbidly detailed investigation — and because you stubbornly refuse to be rejected and overlooked for the purity which you’ve guarded so diligently.

“What if I’m not as good in bed as her ex?” “What if my body isn’t as nice as his ex?” “What if, when we’re married, he wishes he was with her?”

The reflex reaction of the insecure is to quantify oneself, especially physically: to rush to numbers for security, to resort to inches to feel worthy, to run to the scale to feel loveable.

Here are six truths to help still your heart, quiet the lies, and proceed with compassionate caution and wisdom in a relationship with someone who has a sexual history.

1. Quantifying love quenches love.

The reflex is understandable, but vain. Whether you measure up to anyone else or not, if you buy into the lie that love should be quantified, you destroy real intimacy. When you measure your lovability by trying to quantify your sexuality, you diminish your humanity.

2. Love is personal, not performance-based.

What scares you is that you will come up short in your manhood or womanhood in marriage — that you will always be living in the shadow of your partner’s ex-partners — that your shortcomings and deficiencies will loom over you in the form of inexperience. Remember this: meaningful sex isn’t primarily about a particular sensation, but a particular person(1 Corinthians 7:4; Ephesians 5:31–32) — and only in the God-appointed context of the marriage covenant.

The sustaining benefit of sex in marriage is not the orgasm, but the committed intimate relationship. Don’t buy into the temptation to dwell on the ways you are deficient — the temptation to self-destruct. The gospel reminds us: the Beloved is the blessing (Ephesians 1:6).

3. Love will not indulge in paranoia.

Remember that your defensive reflexes — to assume that you are always being compared to your partner’s ex — are born out of paranoia. If your partner doesexpect you to conform to patterns of her previous sexual partners, they are not ready to date — that is, they are not ready to be trusted with your (or anyone else’s) heart.

If they don’t enforce some comparison on you, do your best to accept that and move on. To linger in paranoid indulgences about one’s shortcomings will corrode your soul and your relationship from the inside out. “The fear of man lays a snare” (Proverbs 29:25): the trap is you. It’s your unwarranted and misplaced fear.

4. Love does not revisit, but covers a forgiven offense.

Bringing your partner’s sexual past up repeatedly will destroy your relationship quickly: “Whoever covers an offense seeks love, but he who repeats a matter separates close friends” (Proverbs 17:9). Obsessions with your partner’s past likely signals that you have some work to do. Talk with some sane, godly (confidential) friends besides your partner.

“Without counsel plans fail” (Proverbs 15:22). The same could be said of a dating relationship. Make your close, trusted, selective friend group the place to think openly in confidence, and make your relationship the place where you speak intentionally and thoughtfully.

5. Love recognizes grace and guards against self-righteousness.

Humble yourself and recognize that your partner with a sexual past may very well understand grace now far better than you do (Philippians 2:3). Jesus says, “Her sins, which are many, have been forgiven, for she loved much; but he who is forgiven little, loves little” (Luke 7:47). To marry someone with a past is not “settling,” but can be a great gift. How maddening that must be for Satan. What he meant for evil — to harm or demoralize us — God often means for our good (Genesis 50:20).

Search your heart and root out self-righteousness so that you’re not blind to see that God may be giving you a partner who is gracious enough to put up with you, because they have received grace. “Blessed are the pure in heart, for they will see God” (Matthew 5:8). Amen, and those who were once impure in heart are sometimes blessed with a vision of God that allows them to boast in God more than all (2 Corinthians 12:1).

6. Love does not need to be the best.

Remember that your identity is in Christ. Again, if you marry your partner who has a sexual history, you will not be the best person in their life in every area of life. Someone in their circles will be more attractive. More competent. Funnier. More appealing. To stake our value in being the best at everything in a future spouse’s life is absurd. If dating is moving towards marriage, and you learn of a sexual history, recognize that you were never pursuing this person so that you could be the best in bed — or the best at anything.


Christians date each other to try to show love, patience, and care to one another, and to give whatever is needed in the other’s pursuit of Christ — for as long as they both shall live. The promiscuous King Solomon knew firsthand: satisfaction is measured, not in terms of what a person can do in fifteen minutes, but what they can do with fifteen years: “Many a man proclaims his own steadfast love, but a faithful man who can find?” (Proverbs 20:6).

By trying to measure up to past sexual partners, we give the past power that it neither has, nor should be thought to have. It is way too easy to become obsessed with a partner’s sexual history. If your partner says, “I don’t think about my ex,” it really could be true. It would be a terrible violence to give someone’s past sins power over them that they didn’t previously have. Give them the grace of knowing that their past doesn’t define them.

Practical Helps for the Conversation

We all have remorse-tailored monsters hiding in our closets. We’ve looked a few of them in the eye. But there is still hard work to do — understanding, forgiving, crying, forgetting, maturing, resolving work — and there are some concrete ways that Christ enters into the conversation about sexual past in a dating relationship.

1. Make the hard conversation a pastoral one, not a private one.

Bring in an older compassionate couple in the church, maybe even with the same story, to protect both of you from sinning against one another in the ways we mentioned above. This can take several shapes. If your partner with a sexual past is already in the company of a church and has been walking in the light of a pastoral team, the resources probably exist there for help. They are known, and they are trusted, and this is a great situation to come into (Philippians 2:22). Bringing understanding mentors into the conversation doesn’t cause the relationship to lose control, but offers the potential of balanced, hope-filled, and biblical perspective and clarity.

While the conversation can be difficult and awkward, it need not be had alone. A wise married couple should remind a dating couple that the dating relationship does not ultimately have the tools to finish the conversation and follow through. A dating couple likely will not make sufficient promises or decisions or resolves within the structure of their relationship to fully address a person’s sexual past. Knowing this is not a defeat, but a mercy. Don’t try to resolve the conversation about sexual past in the dating relationship, but have it to the extent that it’s appropriate. If this topic has been especially painful or difficult for you, it might be helpful to commit to refrain from speaking about it except with an older couple or in premarital counseling.

2. Focus ultimately on present maturity, not past history.

The conversation should not mainly be about the issue of history, but of maturity. Yes, the person with the past, if their sexual activity is recent, needs time to heal before they enter into another romantic relationship. There’s not a magic number of weeks or months to wait before dating someone else after having sex. Andy Stanley recommends Christians who have lapsed into a sexually immoral lifestyle wait a full year before dating again — he says, in fact, that it is the best and most important piece of advice he can give those in this situation. It’s not a law. There may be great wisdom in it. “Desire without knowledge is not good, and whoever makes haste with his feet misses his way” (Proverbs 19:2).

As you consider someone for marriage, their maturity today — the evidence and trajectory of their becoming more like Christ — should be your primary concern. Is this a man or woman manifestly, not flawlessly, marked by the grace of God, a grace that forgives and makes new? Am I willing to entrust and commit myself — my heart, my time, my gifts — to this particular work-in-process child of God?

If you’re a person who does not have an extensive sexual history, you also may not be ready to date. You may not be mature enough to walk with someone gracefully and helpfully who has a sexual history (or any other kind of history). There is a real chance that the one without a sexual history is the weaker brother in the relationship (Romans 14:1–2).

3. Forgiveness happens in a moment, but healing and trust take time.

Shakespeare once wrote, “What’s past is prologue.” It may help us. Perhaps, for our purposes, it might be more suitable to say: “If it’s past, then it’s prologue.” Our past is not our prologue — our past is us, and it takes time to reshape and undo what was done in the first several acts of our life. It doesn’t take God any time to save you (to rescue you from sin and prepare you for heaven), but it may take some time to prepare you for dating. This is not bad news. This is not bondage. It is the gospel — to know that sin is deep and change is very often slow is the Christian life. It is tragic, and normal and redeemable and even beautiful.

Living Beyond the Past

The seeds of grace in a dating relationship where one or both people have a sexual history can bloom in several ways. They can produce a marriage (1 Corinthians 7:7–9). They may prolong a dating relationship for the sake of discernment. Grace may reveal that one, or both, are not ready to date each other. At least not yet. Wherever God may lead you, you can’t control another person’s heart, so strive to show them unrelenting patient love in a way that is most helpful to them, healthy for the relationship, and most of all, glorifying to God. You are loved dearly by your heavenly Father — in the insanity of the dark web weaved by sexual sin, let us love in the manner Paul outlines:

  1. “Do not sharply rebuke.”

  2. “The younger men [are] brothers.”

  3. “The younger women [are] sisters.” (1 Thessalonians 5:2).

Make the standard for conversations about sexual history the same as the standard for elders: “not addicted to wine or pugnacious, but gentle, peaceable” (1 Timothy 3:3). There is no intimacy without pain. There is great gain to be had in practicing and receiving grace. May God grant us the ability to deal graciously with those around us as we all grieve the effects of sin that we feel every day, in every relationship and in every fiber of our being.

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