Regretting a Breakup? Advice for Second Thoughts and Doubts

regretting a breakup

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

If I had to bet, I would say there has never been a breakup in the history of serious relationships and/or marriages, in which the couple didn’t get back together (or think about getting back together) at least one time before they got divorced. In other words, I believe that breakups in long-term relationships almost always consist of trying again. Why? Because regretting a breakup is normal.

There is love there, and longevity, kids possibly, and perhaps the biggest reason: people don’t want to be divorced and/or single again. There’s a lot of fear and anxiety associated with such a big change, and sometimes people think staying is easier, even though they know deep down, being apart is the right answer.

But there’s another reason why I think regretting a breakup frequently happens, and that people usually get back together at least once:


When a person ends a relationship, there are two voices in his/her head. Let me know if this sounds familiar:


1. You did the right thing.

This is your gut talking to you. Your reality. All the build-up of working up the courage to pull the trigger. All the times you were sitting there with the person, knowing that things just weren’t right, realizing this person wasn’t making you happy, seeing the red flags more clearly as time went by.

You now feel relieved, like a huge weight has been lifted off of you. You feel proud of yourself, self-assured, confident, and like you now have dignity and respect for yourself for having the courage to be alone again. You’re also happy about the prospect of finding someone who will truly make you happy.


Jan Leasure - Mortgage Lender and Certified Divorce Lending Professional


2. You shouldn’t have done it.

Regretting a breakup is all abou fear that you will regret it later on. Anxiety that you will never meet anyone again and you will be alone forever. Fear of going on dating apps and having to date strangers. Fear that you won’t have plans on Saturday nights or holidays. You start to feel like maybe this person wasn’t so bad. Maybe you can live with the negatives. You have fear that your ex will meet someone new really quickly and end up happy and glad you broke up with him/her. What if you will want him/her back but it’s too late?

The best example I can give of these two voices in your head is, remember the movie, Animal House? Larry’s date was passed out in his fraternity bedroom and an angel popped up on the left side of his head and said, “Larry, be a nice guy. Take her home.” Then the devil popped up on the right side of his head and said, “F*** her, F*** her brains out.”


Michele Heffron, Divorce Coach, Life Strategist


So, how do you handle the two voices? Which one should you listen to?

Here’s one divorced woman’s breakup story:

I broke up with my boyfriend 3 weeks ago because there were starting to be too many red flags. He messaged me today and was very sweet and now I am really struggling. I think deep down I know I made the right decision, but I love and miss him, so this is very hard right now. I know that no one is perfect, so how do you know when to not settle for someone but understand that everyone has flaws too?

He is loyal and loving but can be very emotionally immature and angers quickly. That is why I ended things. But him reaching out has really got me regretting things and wondering if I could have made a mistake.

This question in her post is what I’d like to address:

How do you know when to not settle for someone but understand that everyone has flaws too?

This is perhaps the most difficult question in regretting a breakup and breakup doubt. We all know that in every relationship—even the healthiest and best ones, that there are going to be things that bug us, things that drive us crazy, even. But there’s a difference between those things and red flags.


Maci Chance, Denver realtor


Red flags are things you know are dead wrong. Like if you see excessive drinking and you suspect addiction. That’s different than someone who leaves his or her wet towel on the bed. A red flag might also be drug addiction or cheating or lying or bad parenting.

In this reader’s case, she writes that her boyfriend is emotionally immature and angers quickly. Is that a flaw or a red flag? What’s the difference? I don’t know the guy, so I can’t draw a conclusion about him personally, but there are a couple factors to consider.

One, maybe this woman is scarred from a previous relationship where the guy was violent and so this guy’s anger scares her, or, maybe this guy really is scary when he gets angry. Maybe he flies off the handle super quickly.

The best advice I can give her is to talk to him about her concern and see how he reacts. She will know right away. She might say something like, “I feel like when we disagree on something, you get really emotional and angry quickly. This makes me uncomfortable. I would like to work on how we can communicate better.”


Vestor Capital


He might respond by grabbing a beer out of the fridge and saying, “Screw you, I’m not that way at all!” Or, he might say, “I’m so sorry you feel that way, I will work on it. Next time you see me acting that way, let me know.”

If you break up with someone and you tell him/her why, and the person is willing to work on it, let’s say by offering to go to therapy, I think that’s a huge positive. If the person is closed-minded and wants things to stay the same, that’s helpful for your breakup doubt. You will know you did the right thing.

When regretting a breakup and/or having breakup doubt, I think you have to ask yourself how happy you are on a daily basis. Are you happy with this person every day or just some days or just one day a week, on average? Are you disappointed every so often or frequently? Are you frustrated with the way things are a lot of the time? Do you respect this person? Do you trust this person long-term? Do you enjoy being around this person ALL the time, sometimes, or rarely?

The thing about breakup doubt is, you have to realize that the person and the relationship will most likely never change. Sure, as I said above, the person might offer to work on themselves, but I think in most cases, you have two choices: take the person and the relationship “as is,” accept it and stay, or breakup. And that can be a very very hard decision.

In relationships, even though you know it’s bad, it’s hard to give up the good.

In regards to this divorced woman and her breakup doubt, I think there is a good chance she will get back together with this guy. But I believe it will be temporary. I am not judging her at all. I have personally broken up and gotten back together several times in a few different relationships in my life, including my marriage/divorce. I get it.


Nix Baker Wellness and Therapy


Breakups are a process. Sometimes letting go means little by little, and that can take days, weeks, months or sometimes years. I know a woman whose divorce lasted for 5 years because she kept trying to make the marriage work. So, she’d hire a divorce attorney, start the process, reconsider, and they would work it out for a few months or even a year at one point. Then she would repeat the process.

The thing about breakups is that they might be easy, initially. It’s staying broken up that can be really hard sometimes. That heartache of missing the good things about the person can seriously stay with you for a long time, even years. And feeling that desperation of not wanting to be alone again is a killer. But the good news is, you are so much stronger and more resilient than you think. Going through a breakup where you pulled the trigger can feel empowering and can give you a lot of self-love if you can just get through that period of doubt.

Here’s a reference to another movie, The Shawshank Redemption. Remember when Andy DuFrane had to crawl through a tunnel of sewage to get to the outside of the prison? Breakups are like that. If you can make it through the tunnel of doubt, loneliness, and fear, you will come out free, with a better life on the other side.

This article was originally published on The Good Men Project.

Like this article? Check out “9 Signs of a Healthy Romantic Relationship.

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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