Baggage is OK! The Benefits of Dating Someone Who Is Divorced

dating someone who is divorced

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

Dating someone who is divorced is complicated. Very complicated. You’ve got an ex in the picture, you’ve got his ex, you’ve got the children, you’ve got his kids, you’ve got lifestyle changes, you’ve got financial issues , child support payments and more.

Let’s be honest. In dating someone who is divorced you’ve got baggage. Both of you. It’s not an insult. I myself am divorced and I have baggage. Everyone does. Even people who aren’t divorced.

All that said, there are benefits to dating someone who is divorced. Here are 5:


1. Divorced people are real.

The person I am today and the person I was before I was married are very different people. What’s in my core is the same, and that’s no small thing, but looking back, before marriage I had a naïve way about me that all changed when I got divorced. It’s sad, but there was this innocence and rose colored glasses.

But now, I feel more authentic, meaning I see truth and I don’t  sugar coat anything. I think many divorced people are like this, and it’s a great quality, because everything is very honest and upfront. I’m not saying married people aren’t real. They just haven’t been through a divorce, and divorce does something (neither good nor bad) that perhaps makes you wiser, more authentic, and more willing to just be you.


Serving divorced men and women in creating a new will and trust


2. Divorced people are willing to commit.

For a short time after divorce,or in some cases forever, some divorced people become non-committal. “I’m never doing this again” is their attitude. But for the most part, the majority of divorcees are willing to make a commitment again. Ask any divorced person, and so many  will say, “I loved being married. I was just married to the wrong person.” In other words, if they committed once, they are willing to commit again.

3. Divorced people have less time and are therefore less demanding of your time, less likely to analyze the relationship to death.

I feel like with kids’ schedules and activities and a job and a business, my busy and complicated lifestyle doesn’t leave me much time for drama. In dating someone who is divorced, you have time to think about the relationship, overanalyze it, create problems that don’t exist, and be demanding of the other person’s time. I think many divorced people just feel grateful for any alone time they get with the person they are dating, and so it becomes much more valuable and meaningful. We appreciate the person more.


Bridging the Gap Between Conflict and Resolution


4. Divorced people enjoy being loved.

If you think about the end of your marriage, or for some people, the entire marriage, you probably didn’t give or receive much love. Or maybe you gave it and didn’t receive it or vice versa. In any case, when you get divorced and you meet someone, it just feels good to feel loved. I think a lot of divorced people aren’t as afraid to show their level of affection or how much they care. Being vulnerable might feel more okay than it did pre-marriage.



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5. Divorced people go on fun and interesting dates.

Just like being loved, at the end of your marriage, you most likely did not go on dates or spend quality time with your now ex, and if you did, you were probably fighting the whole time, making whatever you were doing not so fun. I have done so many wonderful things since I got divorced. One guy invited my friend and I to stay at his beautiful ski home on a mountain in Colorado, another guy made an Israeli dinner for me, and then played his guitar and sang to me, and my now boyfriend and I have gone on so many wonderful, memorable trips together.  Divorced people plan really fun dates, and you end up experiencing new things that lead to new interests.


In closing, here is a quote from my novel, FREE GIFT WITH PURCHASE that addresses dating after divorce in regards to baggage.


“People with baggage are still capable of finding love again, and the difference between those who do and those who don’t is pretty simple. The ones who end up happy are the ones who put the bitterness and anger bags down, the ones who stop thinking like a victim, and find the guts to go out and find the life they want, the life they feel they deserve.”

Like this article? Check out, “Dating After Divorce: Advice, Tips, and Why This is an Exciting Time!”


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Jackie Pilossoph

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.

2 Responses to “Baggage is OK! The Benefits of Dating Someone Who Is Divorced”

  1. Graham Jackson

    The last paragraph sums it up nicely.

    I’ve been on quite a few dates, and have no issue with a female wanting to talk about her ex’s. I can learn a lot about a person by listening to them, and where they are emotionally. We all have baggage. It’s how we deal with it that matters.
    I would be more concerned by someone that totally ignored their past. You never know what ‘bomb’ is waiting to go off.


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