Tough Call! Should This Divorced Woman Choose Her Ex Or Her New Boyfriend?

divorced woman

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

I’m going to give you the story in a nutshell. A divorced woman has been officially divorced for a little over a year after a 20 year marriage. They had some financial and other issues and he refused to go to counseling. She said he is a good dad, but she felt nothing for him.


She started dating a guy who has never had kids and describes the relationship as “a dream.” He is great with the kids, but she realized a few months into it, she was still grieving the divorce. She found she missed her ex and felt guilty.


Reaching out to the ex, they started hanging out for a couple weeks, until she began thinking about the new guy and missing him. She is now seeing the guy again and the ex doesn’t know.


She said she doesn’t know what to do. She said faith plays a large role in why she is still considering getting back together, that she believes in forgiveness and accepting people for who they are.


Want Financial Security After Divorce?


She describes her ex as “passive, the life of the party, simple.” The new guy “takes initiative, responsibility and is thoughtful and caring.”


She said if she didn’t have kids she’d choose the new guy. Her ex has agreed to go to therapy. She said she feels like she might be “settling” if she gets back with the ex. She said she desperately wants to make a decision but she can’t.


If you have advice for her, comment here!


In the meantime, I have a few thoughts. I’m not going to tell her who I think she should choose, but I will offer a few things I see as an outsider, which she might not be able to see. Please realize that I am not judging, I just want to bring up some things to consider.


1. It’s normal to miss your ex. It doesn’t mean you should get back together.
2. It’s waaaaaay too soon to determine if the new guy will work out, so she is taking a risk if she chooses him. I guess what I’m saying is, usually a relationship is bliss for the first year or two, at least.
3. There’s a difference between missing someone and feeling guilty. You shouldn’t get back with someone because you feel guilty. It will never work.
4. She missed her ex when with the new guy. She missed the new guy when with her ex. Is there something missing with both men? Is neither guy the right guy for her?
5. She said she believes in forgiveness and accepting people for who they are. She can still do that: forgive her ex and accept him for what he is without getting back together.
6. She really needs to listen to her own words in the way she describes these two men.
7. If she didn’t have kids she would choose the new guy. That speaks volumes. That said, the two of them are still in LaLa Land because the relationship is so new.
8. She feels like she might be settling if she gets back with the ex. Huge red flag that scares me.
9. Why does she have to make a decision? Maybe let things play out. Consider being honest with both guys and see how they react. She isn’t committed to either one (unless the new guy thinks they are exclusive.)


Katz and Stefani Family Law Attorneys


The thing is, she really should think thoughtfully and carefully. This decision will affect the rest of her life. I do want to say that she mentioned having financial problems. I would encourage her to work on her professional life to improve that situation. Maybe the focus needs to be on her kids and her career and put these two guys on the back burner.


There is something about work and independence that lends self-worth and confidence, not only in oneself, but in your decision-making abilities. Does that make sense?


I will be wishing this dear, sweet woman the best as she struggles to find true love and happiness. I give her a lot of credit that she is considering reconciling. I only hope that in the end, she does what is truly right for HER and her kids, not out of guilt or a sense of obligation to anyone. It sounds trite, but it is true. Life is short and when you find love, I say grab it–whether that means with the ex, the new guy or neither!

Like this blog post? Check out my article, “Divorce Advice: 9 Things For Rock Bottom” 




Listen to the Divorced Girl Smiling podcast View the DGS trusted divorce professionals! Divorced Girl Smiling is now offering a private, no-cost, one-on-one phone consult

Sign up for the Divorced Girl Smiling newsletter to get articles on divorce and dating.

Sign up


    Divorced Girl Smiling welcome video
    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:

    One Response to “Tough Call! Should This Divorced Woman Choose Her Ex Or Her New Boyfriend?”

    1. Keith

      This is almost my story to a T. I am the new bf. I am married and now in the process of divorcing. She was married when we started seeing each other. She divorced in Dec but I was still married. After her divorce she was trying to see me and her ex without me knowing but I found out. She doesn’t know I know she was seeing him and me. I broke it off blaming my trust issues. Now her ex has moved in with her.
      The faith statement sounds just like the situation with my now ex gf. Her ex stated one day he wanted a divorce. I believe it played right into what she wanted. Time off from marriage to have a ‘legal’ fling. Explore her wild side. Imo she still has feelings for her ex and the fact that my divorce is ongoing left her a little empty/lonely. Her ex didn’t think she would go through with the divorce and was surprised when she did. During one of their talks she told him she met someone(me) after they divorced(it was actually 11mos. before). He was shocked that she found someone that wanted her, which turned his ‘letting her go’ into a failed attempt at making her crawl back to him. Since I ended our relationship because I found out what was happening, now she wants him back. I believe he did me a favor because I have seen through so many lies on her part(very religious up bringing). It seems she thinks she’s perfected lying. Although I could never be with this woman now, I believe her and her ex’s relationship is doomed, again, based on her withholding information from her ex of her infidelity. I don’t believe she’ll be able to fix what was broken unless she tells him the entire truth but she knows that will destroy him and their new relationship. As far as advice? As long as she is truthful with her ex AND her bf about what she wants to happen, it will work whatever she decides. In my situation, this woman has yet to have a ‘face to face’ conversation with me. She MAY know it would end with me walking away like I did when I caught her the first time. I’m certain she would have a different version of events but she won’t talk to me now fearing her ex will ‘find out’. Is she insecure?


    Leave a Reply

    Your email address will not be published. Required fields are marked *