Question 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. 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?

Reply

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. (To keep reading my reply, click over to Boundless.org.)