How to End a Relationship on Good Terms with the Prince Turned Frog

how to end a relationship on good terms

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

When I got an email from a reader asking how to end a relationship on good terms, I immediately thought of the famous post it note that Berger gave Carrie on Sex and The City. that read “I’m sorry, I cant. Don’t hate me.”

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Here is the email I received:

I recently met a guy and we really hit it off! Born in the same year, we shared many of the same memories of growing up. We talked about a few of the important things up front and it seemed as if we may be a great match. After a couple of weeks, many negative traits surfaced and I realized that he was not the guy for me. I am having difficulty telling a guy, who I was so into a couple of weeks ago, that I am no longer interested. How do I end the relationship on good terms and explain that my feelings changed so quickly without hurting him or being unkind?

Without sounding completely heartless, my gut reaction is that you’re asking me how to break up with a prince who turned out to be a frog.

First of all, I’m sorry that happened to you. I can attest firsthand to the disappointments of dating after divorce. You’re alone and lonely, and then you meet someone and you get your hopes up that finally, after dating either losers or men who broke your heart, you find someone who might actually be the one. When the shoe drops, it’s frustrating, sad, depressing and it feels hopeless.

Not to mention, if you’re the one who decides it isn’t right, you now have the burden of how to end a relationship on good terms, along with the guilt that accompanies breaking someone else’s heart.

My first piece of advice to you is DO NOT feel guilty for breaking up with him. The two of you were dating. That’s it. You didn’t make any promises, you aren’t married or engaged, and you aren’t ending the relationship because you want to hurt him.


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According to Wikipedia, the definition of dating is “a process whereby two people meet socially for companionship beyond the level of friendship or with the aim of each assessing the other’s suitability as a partner in an intimate relationship or marriage.”

“Assessing the other’s suitability as a partner” is another way of saying you’re test driving the vehicle. You’re figuring out if he or she is the one. In this case, you realized he wasn’t. That’s OK! It happens all the time.

The thing is, he will undoubtedly be hurt and that’s sad. But when dating, you are always taking that risk. He will eventually get over it, meet someone else with whom he will break it off or she will, or he will get married to her.

My advice for how to end a relationship on good terms:

Just be honest. I can’t stand it when someone breaks up by saying, “I got back together with my ex boyfriend,” because they don’t want to hurt the person. That’s such a cowardly way out.

In my opinion, you are hurting the person much more by this lie because the person will have hopes that you and your ex will break up again and you’ll come running back. He will be sure of it and he will wait around, which will prevent him from healing and being able to be in a healthy relationship with another woman.


You don’t have to be brutally honest. Saying, “Your toenail cutting grosses me out,” or “You have bad breath all the time,” isn’t necessary. Try something like, “I’ve had such a great time over the past few weeks, but I don’t feel I want to pursue this relationship any further. I’m really, really sorry. I don’t want to hurt you and I’d like to be friends with you. I just don’t us as a couple in the future. I hope you understand how sorry I am that it didn’t work out.”


Several years ago, a guy broke up with me on our three month anniversary. “It’s been three months and I feel like I should be in love with you and I’m just not,” he said. Ouch. Don’t say that. It was very hurtful and mean spirited, in my opinion. If I brought it up after almost 20 years, it must have hurt me pretty deeply!


My last piece of advice on how to end a relationship on good terms is, think of it this way. Breaking up with this guy is not only giving you the freedom to meet Mr. Right, but it’s giving your frog a chance to meet a woman who might adore him and love him madly. Don’t we all deserve that?

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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