Pandora’s Box

Recently, while cleaning out my office at home, I came across a small turquoise gift box with Macy’s written across the top. Actually, my daughter was the one who found it. (She was helping me de-clutter to earn some money for yet another Hello Kitty item.)

When I saw the box, its corners worn white from years of transport, I instantly knew what it was – old love letters. They were letters that I’d read and re-read before, so rather than stop to take another look, my daughter and I continued with the task at hand. But that small box prompted an entire conversation in my head about the intersection of love or at least dating and single parenthood.

Remember when you were a kid and if some little boy or girl liked you, they might write a note bearing their soul and asking if you felt the same? In other words, “Do you like me? Check yes or no.” Except, the letters in my box weren’t quite that simple. In fact, most of the letters in that box came from boys from my middle and high school years, so they were a little bit more nuanced (a little). One of those boys, now a very grown man, is also still a dear friend. To protect the innocent I won’t go into detail, but I must say, that I was reminded of how simple adolescent love can be and how much more complicated it becomes as an adult.

AND how incredibly complex it becomes when you are a single parent on the dating scene.

You better believe whoever gets to meet this sweet face has got to be SERIOUS.

So, ladies and gentlemen, welcome to my world. I cannot simply ask a man if he likes me. (First of all, I tend to carry a sack of pride too heavy for that.) Even if I did, that question would be followed by an entire series of questions based on his response. Obviously, if he “checks” no, the conversation is over. But if he “checks” yes, I have a few more things I need to know:

  • “Are you single?” (And yes, I have to verify that.)
  • “Do you have any children?”
  • “How do you feel about dating someone with children?”

Now let’s assume that Hypothetical Man and I get past all those initial questions, and let’s say that he is a parent himself. We now have to figure out how to make time to see one another. I’m typically not a huge fan of texting as a means of getting to know someone, but it’s often the most convenient option for two single parents. Meeting for lunch is usually doable, but dinner plans – usually based on when your kid actually goes to sleep. And thank God, that on most occasions, my parents are available and happy to babysit, but what if you’re totally reliant on an outside sitter? And sitters cost money, which one often tries to conserve as a single parent.

If Hypothetical Man is not a father, the situation can be even more delicate. He may not have as much patience or understanding about last minute changes to plans, or even the fact that YOU HAVE TO PLAN, sometimes far in advance.

Oh, and when is the right time to introduce your child to the person you’re dating? My personal rule is that no one meets my daughter unless we both agree that we’re in a serious relationship. To date, there is but one person who has fallen into that category. But other single parents might be of the opinion that it’s important for their children to get to know their potential mate as soon as possible.

There are, of course, tons of “single parents dating” resources and groups, especially online. I personally haven’t tried any of the single parent online dating sites, in part because I am afraid, and in part because I picture people going on first dates at their kids’ PTA meetings. (Don’t judge me… It’s my own personal stigma. And I’m trying to overcome it.)

I think that many of my coupled friends would agree that before they were attached, dating was hard. Dating as a single parent, in my opinion, is harder. But here’s the thing, over time, I’ve gotten better at maneuvering in this world. And now that I’ve found my little turquoise box, I have a place I can go when it gets a little crazy. I think that’s pretty good for a little box WITHOUT a ring in it!

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