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Should I date a friend of my ex?

Here’s the dilemma: I don't want to hurt my ex. I was the one that broke up with him. I broke his heart and, even now, I feel so guilty about it.


More than a year ago, I broke up with my boyfriend.  Currently, I am quite interested in another guy that my ex is also friends with.  He started calling me to see how I’m doing.  Over the past few days, we have been talking every day on the phone, and I think he is interested in me too.

Here’s the dilemma: I don’t want to hurt my ex. I was the one that broke up with him. I broke his heart, and even now, I feel so guilty about it.  Should I stop what is happening because they know each other, and if my ex sees us together he may be even more hurt?

I don’t want this relationship to carry on further if I should end it because I don’t want to hurt anyone else.


Thank you for writing. I’m glad to know you don’t want to hurt your former boyfriend and are even willing to forgo a potential relationship if it is the right thing to do. I’m not sure, however, that it is. The problem isn’t dating someone your ex-boyfriend knows, even if he is a close friend. The problem is that something about how you dated, or how you broke up, is making this extremely uncomfortable.

If you had ended the relationship last week or even last month, I would say it’s probably wise to give it a little more time. But it has been a year. This leaves me wondering why you broke up with him. If your reasons were substantive and biblical (he wasn’t a mature believer (or a believer at all), he wasn’t on a good trajectory, he wasn’t leading well, your relationship was sinful), then you have no reason to feel guilty. If your reasons were selfish and petty (he wasn’t cute enough, he wasn’t ambitious enough, he didn’t make enough money, etc.), then even though it was understandably painful, he should be glad that he is no longer dating you. Maybe your guilt arises from how you broke up with him. Were you unkind and immature? If so, confess your sin and seek his forgiveness, if you haven’t already.

Whatever the circumstances surrounding your breakup, the fact remains that you are no longer a couple, and you haven’t been for a long time. Any guilt that remains must be one of two kinds: either conviction for unconfessed sin, or condemnation. If the Holy Spirit is convicting you of past sin, confess it. Run to God in prayer and repentance. Turn from your sin and receive His forgiveness. If you’ve already done this but are still struggling with guilt, meet with your pastor and his wife (or another trusted, older couple in your church) and confess your sin to them. James 5:16 says,

Therefore, confess your sins to one another and pray for one another, that you may be healed. The prayer of a righteous person has great power as it is working.

If, however, Satan is condemning you for past sin, and you have already confessed it, then it may be that you need to memorize the truths of the Gospel and begin professing them in prayer. Romans 8:1 says, “There is therefore now no condemnation for those who are in Christ Jesus.”

Are you a Christian? If you are trusting in Christ alone for the forgiveness of your sins, then when Satan accuses you (Revelation 12:10), you can acknowledge that “Yes, I am a great sinner; but Christ is a great Savior!” Claim the righteousness that Christ purchased at the cross, setting those who trust in Him free from the penalty of their sin. Jesus paid the price our guilt deserves so that we are washed clean. Spend time meditating on the glorious truths of Scripture beginning with Ephesians 2, Colossians 1:21, Ephesians 5:8, Romans 6:17, 1 Peter 2:10.

Once you have confessed your sin in prayer, you are free to move forward. While you are commanded to love this man as a brother if he is a believer, and to be kind to him if he is not, you are not tasked with tending his heart. If the standard for a new boyfriend after a breakup is “only date someone your old boyfriend doesn’t know,” or “only date if you’re sure it won’t hurt anyone’s feelings,” you may be arbitrarily, unnecessarily, and unhelpfully limiting your options. I have watched the single men and women in our church date in ways that leave them without guilt if things don’t work out. More than that, after a little time, they are free to date someone else within the same church. This is so helpful for forming godly matches.

If your new friendship leads to dating, ask him to tell his friend (your ex) about his plan to date you. Then conduct yourselves honorably in all things, by the power of the Holy Spirit. Don’t be afraid to be seen together, but do so in kindness, being sensitive to your old boyfriend’s feelings without taking responsibility for them. And pray for him.

A word to readers who aren’t presently dating anyone: This question is a helpful reminder that how we date matters to the life and health of the body of Christ. Believers should date in ways that are biblical — honoring to the Lord, and honoring to one another. To borrow from another Boundless author, you should be able, at the end of a failed dating relationship, to sit beside one another in church and not feel embarrassed or guilty.

Believers should strive to date (or court) in ways that are above reproach, to not defraud or take advantage of one another. As 1 Thessalonians 4:3-7 says,

For this is the will of God, your sanctification that you abstain from sexual immorality; that each one of you know how to control his own body in holiness and honor, not in the passion of lust like the Gentiles who do not know God; that no one transgress and wrong his brother in this matter, because the Lord is an avenger in all these things, as we told you beforehand and solemnly warned you. For God has not called us for impurity, but in holiness.

When we obey God in our relationships, it is much less painful when two people who formerly dated one another each go on to date someone else. That is not to say it won’t be difficult, but that we can work through the sorrow when we share the goal of Christ-glorifying marriages.  We should be for one another’s purity and holiness, as well as for one another’s joy. When we are, it is much easier to rejoice with those who rejoice — in this case, a former boyfriend or girlfriend being glad when their ex begins a new God-honoring relationship.


Candice Watters

Copyright Candice Watters 2016. All rights reserved.

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About the Author

Candice Watters

Candice Watters is the editor of, a weekly devotional blog helping believers fight the fight of faith by memorizing Scripture. She is the author of Get Married: What Women Can Do to Help it Happen. In 1998, she and her husband, Steve, founded Boundless.


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