It’s Complicated! Relationship Advice for A Divorced Woman

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

relationship advice

The Sun-Times received this letter from a divorced woman asking for relationship advice.


I am at a point in my life where I am questioning my relationship. I feel like it could be several things, such as not feeling like I have forgiven myself for my decisions and therefore don’t love myself fully; not feeling the welcomeness and acceptance of my boyfriend’s family, including his mom and teenage daughter, because of her past actions and the possible influence on my kids (6, 8 and 10). They are ultimately my number one responsibility. I question the need to step back from the relationship so I can come to terms with myself and fully love him and not be a “negative Nancy”. He and I have known each other before the divorce and got together immediately following my separation. HELP!!!! 

Thanks so much for reaching out. Your love life sounds really complicated right now, and not very healthy. That said, just by reading your e-mail, I am detecting a few really, really good things you have going for you.

First, it’s seems you are a person who is self-aware, which is half the battle when it comes to admitting fault and mistakes, making good choices and thereby obtaining self love.

You think you haven’t forgiven yourself for past decisions. Have you ever asked yourself why? Whatever you did that needed self-forgiveness, was it so bad that it’s unforgivable or are you wrongfully punishing yourself? I have to believe the latter.

Secondly, I love how you said your kids are ultimately your number one responsibility. Do you know how many divorced men and women forget that? A lot. In my opinion, divorced parents (just like all parents) have the responsibility to be completely unselfish, and do what’s best for their children.

In your case, be honest and ask yourself, “Is being in this situation the best thing for my children?” I’m not saying it is or it isn’t, I just want you to be honest with yourself because you just told me that your kids are your number one responsibility. If they are, then take steps to back that up, whether it be “stepping back” as you said was a possibility, or taking steps to make things better in your current situation, such as counseling or putting new rules down for both his children and yours.

The part of your e-mail that unnerved me (actually it was like a punch in the stomach) was the end: “We got together immediately following my separation.” I have to be honest, that scares me. Why?

Perhaps you never let yourself grieve your divorce? Did you have any time to be alone and reflect on what happened in your marriage? Did you try to cover up the pain of your separation with the Band-Aid of a new relationship? I’m not judging you, I promise. I’m just trying to help you figure out if you are in your current situation for the right reasons.

You might want to try talking to your boyfriend, openly and honestly. Tell him how you feel. He might become upset. I know nothing about him, but just be loving and kind and truthful. I’m a believer in getting all your feelings out on the table before things get really bad, and before you find yourself going through another divorce.

Lastly, I want to address something that might strike a nerve, but I’m going to say it anyhow. Are you afraid to be alone? If you are, that is completely understandable. Being alone is scary. But ask yourself, “Is it better to be alone for a period of time, which could open the door for someone who is more right for me and my family to come into my life?” And “Is it better to be alone than in a situation that has so many issues already, and that more importantly isn’t healthy for my children?”


You are anything but a “Negative Nancy.” You are a divorced person who is being wise in questioning a situation that seems like it might not be a good fit for you and your kids. That’s not being “Negative Nancy,” that’s being “Smart Sandy.”


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    Editor-in-chief: Jackie Pilossoph

    Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. 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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