If At First You Don’t Succeed: How Writing Resembles Dating

By Guest Blogger Cynthia Patton


You might not believe this, but writing and online dating have a lot in common. How do I know this? I’ve been writing (and sadly, dating) for a considerable period of time. Admittedly, I’ve been writing far longer, but after a decade spent using multiple apps and sites, I’m practically a certified dating expert. (Although my lack of success with said dating might undercut this claim.) In any case, I think I’m qualified to make a few comparisons.

For starters, writing and dating both require a proactive approach and a thick skin. Think rhino hide. They also demand that one embrace rejection as part of the process. If you are a writer of any genre, you know the drill. You send out work, it gets rejected. You brush yourself off and submit again.


Dating is more or less the same. For example, a couple years ago I was seeing a therapist. He experienced an unexpected personal crisis and cancelled our fourth date. He explained his reasons, which made sense. Nevertheless, I was disappointed and sad.

The therapist wasn’t sure when he’d be ready to resume dating, so he didn’t want me to hang around, waiting. He wanted me to get back online and “explore new possibilities.” A girlfriend later quipped that’s maybe what he wanted, but I think he needed time to process what had happened. In any case, it didn’t really matter what was or wasn’t going on. For whatever reason, the therapist wasn’t ready to date me.

I accepted his position as graciously as I could and wished him well. Then I spent several weeks feeling sorry for myself. Why, I wondered, couldn’t I find a decent boyfriend? I’d been in a relationship that lasted much of 2010, but since then it had been a steady stream of coffee dates and guys who couldn’t commit. Sure I’d remained friends with most of them, but after eight years of single life, I wanted something long-term. I was tired of making small talk over coffee or a glass of wine.


Dating hasn’t been as easy or as simple as I once thought. Guess what? Publishing isn’t either. The trick is to not take it personally. (No small task, I know.) Accept the result and move on. It’s not about you. Trust me, it’s never about you.

It’s true that sometimes people get lucky. Really lucky. Don’t get me started on my friends and family members who met their current significant other while in the midst of a divorce. I’ve put in way more time and effort and I’m still very much single. Not fair!

Life isn’t always fair. Neither is writing. So I let the therapist go and went back online. Within days I had five men pursuing me. Four asked me out. Three never made it to the second date, but one asked me out again the very next day and we dated for two years. Dating and writing are both about timing.

The therapist is back online and dating again—but not with me. I can see now that the relationship wasn’t a good fit. More and more I’m accepting the therapist’s assertion that dating, like writing, is a numbers games. As he put it, you try on a lot of different shoes and see what fits best. Did I mention he was Italian?


Bottom line: if I want to see my writing in print, I have to send it out over and over despite rejections that sting. If I want to have a man in my life, I need to keep dating—despite all the weirdness, uncomfortable situations, and yes, rejection. I need to remind myself, again and again, that rejection isn’t personal, it’s not a measure of my worth. It’s a simple matter of taste and timing. Nothing more.

When you eventually find an editor or agent who loves your words or a guy who finds you beautiful despite your flaws—and you will, I promise; stick with it and you will—oh is it ever worth the wait.

Now get out there and write.

Or date.

Or both.

3 thoughts on “If At First You Don’t Succeed: How Writing Resembles Dating

  1. Yes, to all of this! The only difference for me, dating again at 64, is that sometimes it works to just stop the dating thing. Let it go for a while, then try again. With writing, I never feel that I need a break from it, it isn’t toxic to me even when my work gets rejected. And that’s because I have written what I intended to write, and I know it’s good, at least to me. And I am ok if you don’t value it as much as I do. But with dating, I have to take long breaks because it messes with my confidence and, for the life of me, I can’t really remember why I need a man at this point in my life. (or a woman, for that matter). But don’t take away my writing days!

    • Chris,
      I think my journey as a writer this year has been a journey towards this thing you are talking about – the thing that is happy just to do the writing. For awhile there, it was feeling toxic for me. I got a bit caught up in the who was doing what and where and how, and it was terrible!! Lately, particularly since I am so busy with other things, I’ve been getting reminder after reminder about how much this writing thing is a gift. Such a better place to be!

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