The First Breakup After Divorce Hurts More Than The Divorce

first breakup after divorce

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

Divorce is devastating. For everyone who goes through it. But there’s something that I think might be even worse: the first breakup after divorce. What I mean is, when you get into your first serious relationship after the divorce and it ends. That’s the case with this reader:


I am a divorced mom of two girls 10 and 12. I have been divorced for 3 years and separated for 5.  I reconnected with an old
college boyfriend who I was crazy about in college. We were madly in love for 3.5 years, he was there when I was going through my divorce which definitely helped, but we broke up about 1.5 years ago. He couldn’t move here (he was 3 hours away and he had children in high school)

 He quickly moved on and in with a woman he worked with, who is 12 years older (he is 48 and she is 60) Is that crazy? And he sniffs around every once in awhile to say he thinks of me every day and still loves me.

Needless to say I was SO broken hearted on all levels. I felt like not only did I get duped by my husband but also put my heart in someone’s hands that I trusted only to get hurt again. I am scared to love but need it as well!   I know I sound like a sad case of not ready to move on, but I am trying to look on the bright side. I have a job that I feel comfortable with, I have 2 great girls, I own my home, I look great for my age (45), I am running the Chicago Marathon in October and also have a “friend” that I am getting to know.    BUT the first breakup after divorce is killing me. Why am I so broken hearted and scared and sad still ? Have you felt like this ??? Is there hope???


 Yes I have felt like this and yes, there is hope!


Alyssa Dineen -
Online Dating Coach and Stylist


First, let me say how sorry I am that you are heartbroken. It’s very hard, I bet. Many times after a divorce, people get involved in a serious relationship very quickly (as did you.) There’s nothing wrong with that. You were probably not happy in your marriage for a long time, (even if you didn’t see the divorce coming and realized it in hindsight), so you felt alone and lonely for years, perhaps. Reconnecting with your old boyfriend brought you back to life. That’s good!

By the way, I find a lot of divorced men and women get back together with old flames, probably because it’s familiar and comfortable and feels safe, but sometimes I wonder if the love is real (not saying yours wasn’t) but it just seems convenient to fall back into something from the past, especially when you are vulnerable from a divorce.

I’m not saying people who reconnect after divorce with old boyfriends or girlfriends is a bad thing, I’m just saying that they should make sure it’s for the right reasons (not because it’s safe, easy, convenient, familiar…)


Michele Heffron, Divorce Coach, Life Strategist



I have a few things to say about what happened to you. Have you ever thought that maybe you are mourning your marriage in this break up? There is a best selling divorce book called Crazy Time that talks about the first breakup after divorce, and how people are in a lot of pain because they are reliving the demise of their marriage and it’s extremely painful.

The book says that sometimes divorced people don’t even mourn their marriage until their first breakup after divorce. It could be years later, which if you think about it, explains some of the failure of second marriages.

People rush into second marriages, and then when that doesn’t work out (because they haven’t thought it through and healed themselves from their first marriage) only then do they begin to heal from the first divorce. So, I guess what I’m trying to say is, consider yourself lucky that you aren’t going through another divorce right now!

I don’t know enough about the situation, but I see some red flags with your ex-boyfriend. First of all, I’d love to know how long he was divorced before he got involved with you. He sounds like a guy who doesn’t know how to be alone.

To go from a 1.5 year relationship to moving in with someone (especially when he has kids) screams “I can’t be alone” to me. I’m not saying he shouldn’t date, but it seems awfully early to be embarking on another serious commitment. And if he’s so blissful in his newfound love, why is he still checking in with you? Does he want to make sure you are still available in case it doesn’t work out for him with the woman? What he’s doing to you isn’t fair. In fact, it’s really selfish and egotistical because he’s giving you false hope. Please recognize that.

Secondly, is the three hour distance what really broke you up? My gut is saying no. Three hours isn’t a big deal when it comes to true love. I have a friend who has been flying (because the drive is too far) every other weekend to see her boyfriend for almost 6 years. And their plans are to continue doing that until her kids graduate high school, which is still 5 years away. Every situation is different but be honest with yourself and ask yourself if distance is the real reason your relationship ended.


MJ Gabel - Sell your wedding rings, diamonds, and jewelry.


You sound beautiful, in shape, and like a good, caring mother with a great job. Focus on that for right now. Why do you have to be with a guy? Take some time off. Run your marathon. I have no doubt love will come to you again. Try to be patient and focus on all the wonderful aspects of your life.

By the way, no need to bash 60 year olds! You and I will both be 60 before we blink. But seriously, right now, ask yourself if you might be mourning your marriage in this first breakup after divorce. You might say, “No, I’m so over that!” but maybe this breakup is subconsciously reopening the wounds from your divorce.

You say you are heartbroken, scared and sad. These are all normal feelings and very understandable. But, when you are ready to get tough and face your beautiful future, things are going to get a lot better.

All the best to you and big hugs!

Like this article? Check out “Your Painful Breakup: 9 Things  You Might Be Feeling”

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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:

    2 Responses to “The First Breakup After Divorce Hurts More Than The Divorce”

    1. Francie

      Hi Jackie,
      I agree with everything you said. You must have the “common sense” gene that I also have. It is sometimes worth more than an MBA!
      Looking forward to meeting you soon.


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