The Benefits of Dating Someone with Baggage

dating someone with baggage

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

If you read the title of this blog and you are offended, no offense, but get over it! It’s no big secret that all divorced people have baggage. It’s not an insult, it’s a fact. That said, when it comes to dating after divorce, here are five benefits of dating someone who is also divorced. Remember, there are exceptions to these, which include the individual person, or timing.
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, because ignorance really is bliss, but I feel more genuine now, meaning I see truth and I don’t try to sugar coat anything. I think many divorced people are like this, and it’s a great quality, because everything is very honest and upfront.

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 most will say, “I loved being married. I was just married to the wrong person.”

3. Divorced people have less time and are therefore less demanding of your time, less likely to analyze the relationship to death. My boyfriend might disagree with this statement (LOL) but I feel like with kids’ schedules and activities, a job, social obligations, and the extremely busy and complicated lifestyles of most divorced people, they don’t have time to think about the relationship, overanalyze it, create problems that don’t exist, and be demanding of the other person’s time. 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.

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 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.

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 took me to an outdoor Dave Matthews Band concert, a luxurious spa and an outdoor music festival. I took him to see a Jerry Seinfeld stand up show. 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.”


Buy novels by Jackie Pilossoph



Featured Expert Articles

Jackie Pilossoph Jackie Pilossoph
Creator, Editor-in-chief, Divorced Girl Smiling
How To Handle Sugar Cravings

The Best Reason To Sell Your Wedding Ring After Divorce

Elaine Koby Mossr Elaine Koby Moss
Vice-president and Senior Advisor, Vestor Capital
Want Financial Security After Divorce? Here’s Your Checklist

Want Financial Security After Divorce? Here’s Your Checklist

Dan Stefani Dan Stefani
Divorce Attorney, Principal, Katz & Stefani
Thinking About Divorce? Here Is Your Legal Consultation

Thinking About Divorce? Here Is Your Legal Consultation

Jeremy Woods Jeremy Woods
Senior Residential Mortgage Banker, CIBC
6 Tips To Getting A Mortgage After Divorce

6 Tips To Getting A Mortgage After Divorce

Leslie Glazier Leslie Glazier
Real Estate Agent, @properties, Certified Real Estate Divorce Specialist
The Divorce Settlement And Your House

The Divorce Settlement And Your House

Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. 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 “The Benefits of Dating Someone with Baggage”

  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.


Leave a Reply

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