Dating After You’ve Been Married: You’re Only Allowed One Carry-On Bag On Board

dating after you've been married

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

I can honestly say that for every single flight I go on, the items in my ONE permitted carry-on bag consist of the following: computer, phone charger, wallet, phone, Xanex, jewelry case, lipstick, keys, playing cards (if I’m traveling with the kids), sunglasses, ticket stubs. It’s not complicated. What does this information have to do with me offering advice on dating after you’ve been married? Plenty.


If relationships were like airplanes, then that would mean you are only allowed to take one carry-on bag into it. What should be in the bag? In my opinion, hope, peace, acceptance, the love you have to offer, kindness, honesty, inspiration, fun, and among the most important, your love of being a parent.


Unfortunately, I think that divorced men and women violate the FAA rule when it comes to how much baggage they carry on to their new relationship. But, let me explain why I think it’s understandable.


Let’s say your marriage or last relationship ended because your spouse cheated. Now, are you supposed to walk into your new relationship and not even think twice that your new guy/girl might cheat? Cheating can be traumatizing to men and women, and being skeptical, cautious, paranoid, and even fanatical really is understandable.


I hate when people say that when enough time has gone by, someone who was cheated on should be able to move on and not even think about it in their future relationships. They obviously are missing the point that the pain, trauma, disappointment, and lack of trust is something that might stay with a person who was cheated on forever.


But cheating isn’t the only baggage I’m talking about that violates the FAA rule. What about addiction? Let’s say a person was married to a drug addict, a gambler, a heavy drinker, a pot smoker? They might go on a date with a guy/girl who has several drinks and be completely turned off. By the way, I’ve actually had men tell me that women who drink heavily on dates turn them off completely. My point is, the experience of someone exhibiting similar behavior to that of an ex (even though they might not be a heavy drinker-just nervous for the date, or maybe they happened to be gambling on the Kentucky Derby and it’s a once a year thing) might bring it all back, and deter the person from a second date or from dating anyone.


There are many other things that divorced men and women put in their carry-on bag that shouldn’t necessarily be in there, and what the baggage is depends on why their marriage ended.


But here is my relationship advice. No one wants more than one carry-on bag (with the good stuff in it) when going into a new relationship. We all want a fresh start, a new beginning, right? So, here are some things you can do to minimize carry-ons in your new relationship and bring only the best things you have to offer.



  • Be open minded. Try to remember that when your was exhibiting the behavior that led to your divorce, your new guy/girl wasn’t even remotely in the picture. Therefore, give them a fair shot. Until they do something (and they might not ever do anything) to arise your suspicions of show red flags, remember he/she is their own person.


  • Try some self talk. Whenever you start to doubt your new relationship because you become fearful of getting hurt, reason with yourself. Tell yourself, “He’s not so and so.” You might have to repeat it several times.


  • Explain your fears to your new guy/girl. Versus becoming quiet and distant, be open and honest and authentic. Explain to them what happened in your past. And make sure to say, “This isn’t about anything you’ve done. You’ve been great. It’s about me and my fears that stem from the past.”


  • Keep your eyes open. Giving your new relationship a fair shot doesn’t mean you should ignore red flags. Trust me. Many people who get divorced repeat their poor choices in partners. Remember that book about a woman who married three alcoholics?


Meeting Mr./Ms. Right isn’t easy, but you’ll find him/her if you listen to your gut, be honest with yourself, and have patience.  But while you are looking for that person through the world of dating, make sure you only bring the “good baggage” to your next relationship. Otherwise, forget the FAA. Your new relationship will be one turbulent flight!


Katz and Stefani Family Law Attorneys


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    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:

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