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The Hardest Part About Dating As A Divorced 20-Something

I was 28 years old when I filed for divorce and became single again for the first time since I was legally allowed to drink.
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Lonely hearts diary open.
Lonely hearts diary open.

I was 28 years old when I filed for divorce and became single again for the first time since I was legally allowed to drink. But walking around the streets of Manhattan, I was just another twenty-something-year-old single girl. I didn't "look" divorced.

I know this doesn't really seem like a big deal -- or if anything, it seems like a good thing, right? No visible scars. I was young, I didn't have any kids and I was in the "typical" age range for dating and all that.

But this meant that anyone I dated automatically assumed that my single status was the same as everyone else's: maybe I had some prior relationships, but I still hadn't found the right guy.

And the way dating works if you're seemingly just-a-regular-girl-in-the-big-city is that there is a common set of expectations around the timeline of how things go down:

  • First kiss: fair game for the first date.
  • More er, intimate stuff: sometime after the third date.
  • Meet the friends: after a couple months of consistent dating.
  • Mention that you're in the process of getting a divorce: ummmmm... ?!!!?

Dilemma. When do you mention that you've been married before?

I had some friends who told me, "You don't have to tell him about your situation, that's none of his business". But those people just didn't understand what being divorced at 28 really feels like. And since you've lived within a marriage, you know better than anyone just how important honesty and trust are to a healthy relationship.

If you get far enough along dating someone where it feels like it's time to broach the topic of previous relationships, you've probably built up some intimacy between you. Therefore, waiting too long to mention, "By the way I'm divorced," might erode some of that trust you've worked hard to establish.

I mean, imagine saying that to someone who thinks they know you. Feels like a huge deal, right? My biggest fear about this situation was that nobody would want to be with me once they found out I was going through a divorce.

The good news is that this fear turned out to be totally unfounded. Here are some of the typical responses I got:
  • Disbelief: "You're divorced?"
  • Digging deeper: "Do you have kids?"
  • Security check: "Is there still anything between you two?"
  • Gathering facts: "How long has it been?"
  • Trying to make you feel good about yourself: "His loss."
  • Awkward commentary: "It's not weird. It would be weird if you were still married." (... the paperwork for my divorce took three years to finalize, I was technically still married for most of my dating life...awkward!).

The common thread through all of this was that the guy on the receiving end of the information was trying to make sense of what it meant in terms of him and me. Nobody ever seemed bothered by this news. Nor did anyone (who was nice/sane) try to use my past against me. Ever.

So fear not. I found that the "I have an ex husband" thing doesn't have to be a big deal in your new relationship as long as you take care of a couple things:
  • Be honest before you get too serious or intimate with someone.
  • Make sure that he feels secure in your relationship with him.

And if you are divorced and out in the wild, dating again, please remember that getting divorced when you're this young isn't "just a break-up." Your ex-husband was a member of your family and since you're still so young, he also probably was a part of your world for most or all of your adult life. Dealing with that kind of loss, especially when the vast majority of your peers just can't relate to your situation is not easy. Take it slow while you heal, and always trust your instincts.

If you divorced in your 20s and learned a lot about love, life and yourself in the process, we'd love to hear your story for our series, Divorced By 30. Send us a 500-800-word essay or an idea for a blog post to

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