Relationship work is what we’ll explore here—especially when the question is whether to date an ex. This isn’t about quick fixes or neat answers; it’s about slowing down and getting honest with yourself. What’s pulling you back—love, loneliness, or unfinished business? What has genuinely shifted since the breakup, in you and between you? We’ll hold space for the mixed feelings, the memories, and the hopes that come with second chances. Consider this an invitation to reflect with clarity and compassion before you decide where your heart—and your future—want to go.
Couples work because they do the work.
The number one question I got was “Can dating an ex work, is it possible to make the relationship work? The short answer is “Yes”. There are couples who connect later in life and are able to make a successful go of it. These couples work because they did the work. You cannot enter into a new relationship with old relationship skills. In other words, if you do the same things over and over again, you probably will breed the same results. But what about when you have history with someone? What about the second time around relationships?
Second time around relationships requires even a higher relationship IQ to make your relationship work. While we may think it’s an added bonus to have history on our side, the reality is that so many of us are scorekeepers. We either haven’t forgiven the past. Or, we haven’t been able to let it go. For that reason, that imprint becomes twice as offensive because we’re still carrying around that abuse or trauma. When we are dating someone new, we are more inclined to forgive because there isn’t a history or pattern that is associated with that offence.
Short Term Memory Can be an Asset to Make Your Relationship Work
So how can second time around relationship work? They work because two imperfect people join together to celebrate their imperfections. I want to say that again. Two imperfect people join together to celebrate their imperfections. Like all successful relationships, they do not score. In fact, developing a short term memory in your relationships can be an asset. By not holding to anything other the then the issue at hand, no score is kept and resentments are minimal. When we act from a clean slate, there is nothing to weigh us down or to compound the problem. We simple address the issue at hand.
Dating an ex can be rewarding. I personally have always tried to shy away from second time around relationships. That was a personal choice. I think what is helpful for those who are contemplating dating an ex is to take a hard look at yourself and see if you have matured since you lasted dated them. It is possible to make a relationship work second time around. What are you bringing new to the relationship? More patience, compassion or better communication skills. Have you identified the behaviors that co-created the break-up the first time around? Is your ex a person that you can live with? Or, are they the one that you can’t live without? These are important questions. If you’re not sure or having a hard time with this exercise, ask a trusted friend or family member.
Second time around relationships can work. But make no mistake. It will require a higher level of commitment. Just because you spent time together, doesn’t mean it was a good time. For many, it may have felt like serving time. So if you have grown, and you see something new and refreshing with your ex. Your second time around could be better than your first. To make your relationship work second time around, set clear boundaries, communicate honestly, rebuild trust slowly, and let actions—not nostalgia—prove change. When growth is mutual, love deepens again.
