can reconnecting with the one that got away ever work out? experts explain

Hoping To Reconnect With The One That Got Away? Here’s What You Should Know

In case you can’t stop thinking about that one person.

Luis Alvarez/DigitalVision/Getty Images

Whether you’re single or coupled up right now, odds are you sometimes think about that one relationship from your dating history that still feels unfinished. Maybe you wanted to make it work with this person, but for whatever reason, it didn’t pan out. And while some people are comfortable leaving their romantic past behind them, others are tempted to try reconnecting with the one that got away.

There are so many versions of “the one that got away” out there, but most of the time the phrase refers to a past relationship that elicits “regret, sadness, or yearning,” explains Jenni Skyler, Ph.D., director of The Intimacy Institute. Oftentimes there was a “lack of closure” when this relationship ended, Skyler says, which is why you might be tempted to reach out and rehash the details of your romance — no matter how much time has passed.

That said, reconnecting with the one that got away can open wounds, hurt feelings, and make the situation worse if handled incorrectly. Since you should proceed with caution (you could be opening a real can of worms here), the following is what to know about reconnecting with the one that got away, according to relationship experts.

What To Do Before Reconnecting With The One That Got Away

luza studios/E+/Getty Images

Before you officially decide that you want to reach out to the one that got away, you’ll want to consider a few ideas to ensure this is the best move for you. First, you need to take what Skyler calls a “self-inventory,” which evaluates if you’re truly prepared to speak with an old flame.

Ask yourself: What do I really want from this? What’s my readiness? What does this person represent for me? What hole am I trying to fill with this person, if any? Does this person remind me of a parent figure, and I'm trying to heal the past through this person? What am I hoping for from this conversation? If you can, write your answers down and take time to reflect on them before your next move. (Remember, there’s no rush here.)

“A self-check will help you understand your motivations as to why you're thinking about reconnecting with the one that got away,” explains Janet Brito, Ph.D., a clinical psychologist and sex therapist and founder of the Hawaii Center for Sexual and Relationship Health. While you might think your actions are totally innocent (you just want to talk!), you could still have lingering feelings toward this person that you should sort out before you dive into a conversation to keep things from getting messy.

How To Reconnect With The One That Got Away

You should also get a bit more information before you reach out: Does this person now have a different partner? How would their partner feel about you two meeting again? Has your former partner done any inner work on themselves? What conditions are different now for you both?

If you’ve asked these questions and you feel you’re equipped with enough information to make a connection with the one that got away, you’re free to go for it, Brito says.

Once you’ve decided that you’re going to (attempt to!) connect with the one that got away, try starting by sending them a simple message like: “It seems like we both have grown and lots of things have changed. I've done my work and it sounds like you'd have, too. I would love to reconnect and have a discussion.”

If they agree to meet with you — whether it be by phone, video, or in-person — try to set standards beforehand for what you want out of the conversation. Be as clear as possible so each person knows what to expect and can mentally prepare. Say something like: “Maybe we can evaluate and see if we're able to find closure.” Or, if you’re looking to invite them back into your life, say: “Maybe we can rekindle a relationship, whether it be romantic or a friendship.”

Can Reconnecting With The One That Got Away Work Out?

AleksandarNakic/E+/Getty Images

In short, yes, it’s possible that reconnecting with the one that got away will work out for you both, Skyler says — especially if you’re just looking for closure. “Humans like closure,” she says. “If there's a possibility for that, without reopening the relationship or threatening any current relationships, that's really key.”

But what if, for you, the goal of reconnecting with the one that got away is to get back together? It can work out, but “you have to be careful that the person is single, otherwise it's just completely inappropriate,” Skyler says. Think about it: Would you want someone coming to your SO asking for their relationship back? Probably not.

All in all, it’s definitely possible that your hopes to rekindle a relationship will be successful — Skyler has even seen it happen in her practice. “It's happened plenty of times,” she says. “The space and distance from the breakup actually lets each person grow and get into alignment so that they're both ready for the relationship at the same time,” she says.

However, before you start calling up your ex, note this: If there was any kind of toxic behavior present in the relationship before your breakup, you should definitely refrain from reconnecting with the one that got away.

“If there was violence, addiction, or other toxic patterns,” it’s probably not a good idea to reach out, Brito says. And in case you didn’t know, unhealthy behaviors can include things like boundary violations, being controlling, or isolating you from family and friends, too.

Basically, if those patterns were there in the past, odds are it’s not going to be different now “unless there was a huge intervention or something drastic happened where the person reconciled with their mistakes,” Brito says.

But overall, “if you’ve both done inner work, you recognize what patterns were not working in the past, and you're in a different space now, you could try this again,” Brito says. At the very least, you might get some closure and insight that will help you move on and be better for yourself and in your next relationship.


Janet Brito, Ph.D., licensed psychologist, AASECT-certified sex therapist, and founder of the Hawaii Center for Sexual and Relationship Health

Jenni Skyler, Ph.D., licensed therapist, AASECT-certified sex therapist, and Director of The Intimacy Institute