My single biggest, most painful mistake with dating

From the first time I saw her face, I knew I’d love her until the day I die.

I can still picture it clearly today. All the other boys in my Middle School were fawning over that one redhead who looked like Mary Jane from Spider-Man (you know…the Tobey Maguire one).

On the other hand, I happened to crush on my classmate in English class who came in every day wearing a ridiculously cute Mickey Mouse shirt and headband. She was the first person I ever had feelings for.

I’d like to tell you that she never even knew I existed. That’s what I really want to write right now because it would hurt less to whitewash the story and remember it a different way than how it really happened. But that wouldn’t be true to myself.

What really happened is that some time later, one of her friends secretly came up to me and told me “You know, Chloe used to have a crush on you for like, forever.”

That hurts because it’s one thing if I never even had a chance. It’s another thing to know that the first woman I ever found myself crushing on actually liked me back and I just let that slip through my fingers!

Looking back, it’s a mistake I’d made many times throughout my dating life. Whenever I found myself romantically interested in someone, I’d fail to unambiguously convey my romantic interest. That’s the key. If you too indirect and treat women that you’re interested in as friends like I did, then you can’t be surprised when you only end up being friends and nothing more.

Here’s an example to show what I mean:

  • Morning coffee or lunch with a coworker? Not romantic because people do this all the time professionally.
  • Inviting a coworker to a group activity with you? That’s ambiguously romantic because friends also do this platonically, and professionals commonly do this for networking purposes.
  • Asking a coworker to watch a movie and have dinner with you on a Friday night? That’s unambiguously romantic because you’ve set up a series of 1-on-1 activities just for the two of you and you’re meeting her on a night when you can stay out late and not have to worry about going to work the next day.

The key is to unambiguously convey romantic interest. If you treat her platonically then of course your relationship will be nothing but platonic. But if you ask her out 1-on-1 to an activity at a specific time and place, then she’ll know that you’re interested in her. And maybe…just maybe…she’ll be interested in you back.

I’ve loved a lot of women throughout my life. I have two competing memories of the first woman I ever loved, and I wish I could remember it the less painful way but that just tastes like a lie. I can tell you with a straight face that most of the other women I crushed on probably never even knew I existed. Maybe I’m whitewashing those memories as well when I say that. But I honestly don’t know and that allows me to honestly remember it that way.

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