Stop Trying to Optimize Everything

There’s one trend I see over and over again in articles, videos, and discussions about dating. It’s a fixation on tweaking every little thing, and it leads to statements like this:

“Don’t ask a girl if she wants to go to a movie, that’s passive and it makes you look weak. Instead, you should be assertive and say let’s go see this movie on this day.”

Here’s the truth. It doesn’t matter. Do you really think if a woman is talking to Henry Cavill or Ryan Gosling or whatever male celebrities are hot right now, and he says, “Would you like to go to a movie this weekend?” she’s really going to lose all interest in him? Or that she’s disappointed and secretly wishes he’d been more assertive? She doesn’t care, she’s too busy being thrilled that he asked her out to worry about the way he said it.

How would you feel if you were talking to an amazing woman, she’s totally gorgeous, you have a ton of common interests, and she laughs at all your jokes. Then she asks if you want to go on a date with her. You wouldn’t care how she said it.

So stop worrying about every little thing, because that worry is going to do more harm than saying something the “wrong” way.

There are two reasons this over-optimization approach is unhelpful.

First, it means you aren’t being present and authentic with her, because you’re not saying what you think and feel, you’re saying what you think she wants to hear. Even if it’s just changing the phrasing, that moment of hesitation and slight disconnect will come across emotionally and she’ll pick up that you aren’t being totally open. Women aren’t mind readers so she won’t be able to say why, but it’ll put her off.

Women want to connect. They want you to be present and authentic with them on a date, because they want to get to know the real you. Women, especially awesome women who have their lives in order and are emotionally available for a serious relationship, they are so tired of men who play games. They are tired of men who don’t speak their mind. They would rather you stumble over your words and get tongue-tied if that’s your honest self than have you pretend to be super suave only for that to fall apart after they’ve been dating you for 6 months.

The second reason to avoid over-thinking how you communicate is that it prevents you from knowing why a potential connection didn’t work out. If you match with a girl on a dating app and you get a bunch of advice on what to say and how to phrase it until you aren’t even really saying what you think it’s practically a canned line… if she doesn’t reply you have no idea what part of it went wrong.

Remember, rejection is not bad.

If you send her an honest message that’s true to who you are and she doesn’t reply, you know she’s not a good match for you. But when we feel unsure of our own worth, every rejection hurts and it makes us feel hopeless. We’re looking for validation, not connection, and that’s why we want to craft the perfect message. Because we care more about getting a response and feeling attractive and desirable than finding a good partner.

One reason we over-think is to protect ourselves. If we have a goal of crafting the perfect message and we get rejected or ghosted, we can think “Well, my message wasn’t crafted right. I need to read more and practice more and understand how to send better messages.” It makes it not personal. But that same shield that protects you from getting hurt by rejection also blocks you from making genuine connections.

Some of my best experiences in dating have come from awkward, weird, or silly messages that I just typed up and sent on a whim. I’ve also gotten rejected, ghosted, or stood up more than a few times. And it hurts, I won’t lie and say it doesn’t, it’s hard to get shot down when you’re just being yourself. But it also feels so much better when a woman is interested because you know that it’s just because of who you are. She likes you for you, and there’s no performance to maintain.

Because let’s be clear, this over-thinking, this optimization of every little facet of communication, it’s a performance. And when you’re performing on a date, you aren’t connecting with a woman, you’re entertaining her. There are plenty of women who enjoy being entertained, and she might want to get into a relationship with a guy that really keeps her entertained, but it’s not real. It’s built on smoke and mirrors.

One day you’ll get tired of the performance and you’ll stop doing it, and she’s going to realize she doesn’t know you at all.

That might seem dramatic given that we’re just talking about whether or not you should worry about the specific words you use when you ask a girl out, but it’s important because this over-thinking is part of a bigger issue.

Are you scared to be yourself?

You might be using advice and information seeking as a distraction from your fear of rejection. That’s understandable, we’re problem solvers by nature. We like to look at setbacks and failures and find where we went wrong so we can avoid that painful sensation in the future. But sometimes there’s nothing to fix.

To quote Captain Picard, “It is possible to commit no mistakes and still lose. That is not a weakness. That is life.”

Self-improvement is a great goal, but you’re better served focusing your time and energy on big improvements. Things like taking care of your body with exercise, improving your mind by reading books, and practicing your social skills in conversations. Put your energy into the highest level improvements, the things that you know will take your life to the next level, and the small things will fall into place.

Stephen Covey, auther of The 7 Habits of Highly Effective People has a compelling demonstration of this principle. He has a large plastic bucket, and two sets of materials. One set is several large rocks which represent important tasks like the crucial aspects of our jobs, exercise, eating, sleep, and so on. The other set is full of sand and pebbles, and it represents the little things, the distractions like checking our email twenty times or scrolling through social media on our phones. Or googling “best first messages to send on Tinder” and reading sixteen different articles about it.

If you put the little things in first, the distractions, the bucket fills up about halfway, but the big rocks won’t fit. They poke over the top and you can only cram in two or three of them. But if you start with the big rocks, the highest priority tasks, then the sand and pebbles will flow around them and fill in the gaps. You can fit all the big tasks and all the small tasks in.

Your time and energy work the same way. If that was hard to follow, you can watch the video yourself and see it in action.

So to wrap this all up, the next time you match with a girl, don’t over-think it. Go with your natural response. Because you want to date someone who likes your natural responses, and if she’s not interested in that, she’s not right for you. You’re not looking for any partner, you’re looking for the right partner, and that requires honesty and a lot of courage.

If you want to get even deeper into how to express yourself more authentically in text and on your dating profile, book a free consultation call with me. You’ll come out of that call with new insights and a clear goal for how to improve your dating life.

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