Thinking Of Separating? Here are Answers To Questions You Might Have

thinking of separating

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

Questions from a Married Man Thinking of Separating by Jackie Pilossoph for Chicago Tribune Pioneer Press

Deciding whether or not to stay in a marriage is not only daunting, but the tormenting dilemma can feel hopeless, since both options – leaving or staying might seem depressing or wrong.

A time of complete uncertainty, confusion and second-guessing oneself, those thinking of separating have countless questions running through their minds, and often times no one to turn to for answers, mostly because the matter is so private. That’s why they sometimes turn to me – a divorced, single mom, and a dating and relationship columnist.


Katz and Stefani Family Law Attorneys


Here are four questions I received from a married man with two teenagers regarding his contemplation of divorce, followed by my answers:

Q: Is there ever a “right” time to do this (i.e. kids’ ages) or are all times bad? Every time I think I have a window to have “the conversation,” some issue crops up that would seem best addressed while a married couple. Or, am I simply afraid and making excuses?

A: First, here are what I’d consider the “wrong” times to ask for a divorce: the start of school, holidays, birthdays, graduations, or your anniversary. It is also wrong to ask for a divorce after a traumatic event that has affected you or your family, such as an illness, loss of a job or the death of a relative or close friend. These times will just magnify what could be a shocking, devastating conversation.

The best answer I can provide about the “right time” is that you will know in your heart that this conversation needs to take place. Bringing it up is brutal. It is scary and sad and almost surreal. Divorced people often say asking for the divorce was the most difficult part of the whole divorce process. There could be a sense of guilt involved, and the stress of not knowing how the spouse is going to react is beyond unnerving. Just remember that there is always going to be something happening in the household, whether you just found out your child drinks or your kid is applying to colleges or your nephew is getting married and you don’t want to spring your divorce on your family during the happy occasion. Life keeps going and it doesn’t really slow down. Furthermore, when the conversation takes place, things won’t be good, no matter what is going on.

The last thing I want to say in answer to this question is that issues with kids can still be addressed by a divorced couple in the same way they can as a married couple. How? The divorced couple must be willing to act in a selfless way by putting their personal feelings about their ex-spouse aside and co-parenting with that person as a team. It’s not easy, but staying on the same page when it comes to the kids, along with the willingness to communicate about the children, is the key to raising strong, healthy kids through a divorce.


Want Financial Security After Divorce?


Q: How does one balance the desire to do what’s best for yourself while maintaining the needs of and minimizing the pain caused to those you love (or at least still care about) by this decision?

A: This sounds like pure guilt, which I think is normal for those considering divorce. The answer is, you can let yourself be happy and take care of your family at the same time. In my opinion, the first step in achieving this is to look into mediation and collaborative divorce. Both are divorce processes that help foster a friendly, non-combative divorce settlement with a post-divorce plan that works for both parties and ultimately achieves the best results for the children.

Q: How does a concerned parent convince him or herself that every failure the kids will face in the future isn’t the direct result of the divorce?

A: This feels like you are punishing yourself for wanting a divorce. It is unproductive and unhealthy. News flash: your kids – like every kid – is going to have failures in life, from which they will hopefully learn and grow. Even kids with lifelong happily married parents will have failures. Additionally, the kids could have failures that are the result of you and your wife staying in an unhealthy and/or unhappy marriage. Kids pick up on everything. Just as you know you are unhappy, your kids know, too.

Q: Why should I assume I will find love again?

You should not assume that. All you can do is hope, have faith and engage in behaviors that attractive healthy, loving romantic relationships in your direction. People ask me all the time if I think they should get divorced. My answer is always the same. If you are getting divorced because you feel you can do better, you should not be getting divorced. If you want a divorce because you absolutely do not want to be in the relationship with your spouse any longer – even if it means you will be alone forever, then you are doing the right thing. I’m not saying you will be alone forever, but finding love after divorce should be thought of not as something expected, but rather as a gift, a bonus…(Click here to read the rest of the article, published today in the Chicago Tribune Pioneer Press editions.)

Like this article? Check out my blog post, “11 Things People Say To Justify Staying in an Unhappy Marriage.”



Buy novels by Jackie Pilossoph
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:

    2 Responses to “Thinking Of Separating? Here are Answers To Questions You Might Have”

    1. Tulsa Divorce Lawyer Matt Ingham

      When considering filing for divorce I strongly recommend the following: plan plan plan. When I say plan that includes planning your monthly finances, your living arrangement, and most importantly planning the lgistics of your children’s daily lives

    2. Greg Allen

      Separation and consequent divorce are the big decisions of life and need huge preparation emotionally and financially. Though it doesn’t hurt less, one cannot keep mourning forever. It’s better to take stock of one’s financial position and plan the future.


    Leave a Reply

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