I Enjoy Dating Myself: When a Sense of Humor is a Requirement on a Date

Here’s a big lesson I’ve learned: I know how to date myself and I have to say, I’m a pretty fun date. I bring laughter to any date. Even the ones where I’m watching paint dry.

I’ve selected one too many men that check lots of boxes but continue to miss a critical one – the funny box. I’ve tried one too many times to date a guy who just isn’t funny and I am always let down.

What baffles me the most is that everyone, and I do mean everyone, says laughter is important. Yet so few men can really illicit a belly laugh from me. I mean, they don’t even seem to try. But I can keep them rolling on the floor with my stories. I’m so good at a funny story that I can entertain myself. After all, I already know all the punchlines. I can carry an entire date. And that, my friends, is how I’ve made many mistakes. I want the laughter so badly that I sometimes ignore I’m laughing at myself.

I can also talk to a wall. Now, this is a learned behavior after years and years of corporate training presenting to large groups. I can talk about anything long enough to engage the party I’m speaking to. When I’m at work I know how to read the room. Similarly, I can also read each man I pre-screen yet I ignore the fact he doesn’t make me laugh. Why? Maybe because I used to believe some people need time to warm up. If that’s the case, I’ve now also realized that person probably isn’t for me. I know for certain I need a more gregarious man. A man who can be funny right from text. And it happens often enough so I know it’s very possible.

Funny without sexual innuendo. Funny without sarcasm. Funny without low brow humor. Just the right turn of phrase or words to put a smile on my face. Sometimes taking something I just said and gently teasing. Sometimes self deprecating. But funny comes across in text despite what anyone claims to the contrary. If it’s there, in text then it follows in the phone conversation in spades. It also follows that the date will be filled with laughter as well.

When I look back, this has 100% accuracy for me. It doesn’t mean every date is a success or the man is a match. But if he’s funny from text and phone he will be able to make me laugh in person despite if I am attracted to him or not. Scott is funny. Even though I’m not attracted to him I still laugh with him often. He is just funny. George is funny. Even though we never met, he can get a solid laugh from me through text and on the phone. Mike, Dan, Tony etc all very funny men. My x, while his humor is mostly unappealing to me in my maturity, is still very funny. Thinking back to the first man I slept with, Dan, he made me cry with laughter – and still does to this day when he reaches out.

I have to stop dating men I don’t find funny. I have to stop giving them way to long to crack a joke and make me laugh.

I’ve really been debating my own list of requirements as I grow older and think I’ve tried enough to let this one slide. Laughter has become a non-negotiable. I believe I’m so lonely I’ve allowed some of those other check boxes to take the place of this one but I know I can’t live without laughing hysterically the rest of my life. I don’t want to keep dating myself. I want to date someone who is funny. Period.

Author: Madeline Harper

My journey through divorce and an emotional and sexual reawakening. Love, laughter, friendships, family and heartbreak included. And there is sex, lots of it, so close your eyes and turn the page if that's not for you! While I started this blog as an endeavor to journal my thoughts and feelings in an attempt to better understand myself, it has become an amazing platform from which I have met some of the most interesting and wonderful people in my life. My path is often crooked, but I hope you will share in the journey with me.

9 thoughts on “I Enjoy Dating Myself: When a Sense of Humor is a Requirement on a Date”

  1. One of the things I learned about women is that if you can make them laugh – and keep them laughing – you stand a better chance with them. From girlish giggles to having them literally rolling on the floor, tears streaming from their eyes and holding their sides and unable to stop laughing. There’s a time for a guy to be serious in his dealings with women but if you can’t make them laugh, well, you’re screwed… and you won’t be in the way you’re expecting to be screwed.

    Liked by 1 person

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