Breakup Advice: How to End it With The Prince Who Turned into a Frog

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

break up advice

In my “Love Essentially” column this week, I answered a woman’s e-mail asking for breakup advice–how to end it with a prince who turned into a frog. I immediately thought of the famous post it note that Berger gave Carrie on Sex and The City. We all know that didn’t go over well! Here’s some breakup advice that’s quite a bit more passionate than a yellow post it note that reads, “I’m sorry, I cant. Don’t hate me.” 

Love Essentially: How to Break up With a Prince Who Turned out to be a Frog

(from Jackie Pilossoph’s Sun-times Media column published today)


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 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. 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 ending the relationship, 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.

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 the breakup is just be honest. I can’t stand it when someone breaks up with someone by saying, “I got back together with my ex boyfriend,” because they don’t want to hurt the person. 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 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?



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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