Why is dating so hard?

The desire to find love is fairly universal. You would think that the world would act as some magical slot machine, sorting through possible combos until you find a viable match to test out with more serious investment. You'd think we'd be able to move through pairings until we all inevitably, and without much effort, find somebody to invest in. It wouldn't guarantee they're partner material but at least a viable relationship for a while?

So why doesn't it work this way? As a coach, I see a couple of things that are getting in a lot of people’s way:


We're tempted to pretend to be something we're not.

We're all familiar with the feeling on the early dates where you're a little bit more coy than you are in real life, a little less crass, or a little more patient. These adjustments can extend as far as dressing more feminine, staying out late when you really like to be in bed early, and so on. It's pretty widespread that we make minor adjustments to how we are acting in the early dates in order to manage perceptions or increase our likelihood of success with the person. But what are we doing on dates if not trying to get to know people?

And we're all sitting here bamboozling each other, with the best of intentions, with a version of ourselves that isn't real.

Now, am I advising you wear your hang-around-the-house sweats on a first date? Of course not. There is an importance to presenting yourself in the best light on the first date. But if you are a tomboy who never wears dresses or skirts, don't talk yourself into believing you need to wear one in order for a man to like you. Not only are you showing this man an altered version of you, it's actually more useful to you to actively screen out the men who are particularly into feminine dressing women, because a relationship with them isn't likely to be the right fit for you to begin with.

We can’t just go through the motions.

Dating is not like lifting weights. It's not just about getting reps in. There is not an inevitability that if you show up to the dates, talk about yourself and see if you like what the other person says, that you'll find a connection. But many of us approach it this way, keeping ourselves at arms length until we see something we like enough to open up our hearts. The problem with this approach is then we're stuck in a Catch-22 of only making ourselves available for a certain type of person that checks boxes for us, potentially missing the unexpected better fit for us.

Now you might immediately be thinking to yourself, "But, Samantha, I already know what I want! What's wrong with screening for it before I get my heart involved?" Well, how well has it been working for you? Is your accuracy 100% that the type of people you do eventually open your heart to end up as long term committed relationships? Are you experiencing any frustration about how few people you feel like are legitimately good fits?

If your system is working for you, don't let me stop you. But I'd guess if you're reading this article, there's something that might not feel quite right. And one thing I'd argue is that you've probably sat across the table from someone you could have really connected with but you had your walls up and didn't notice them.

I don't mean to be harsh here but there are a lot of people walking around dating but in reality, quite emotionally unavailable.

We really don't like (i.e. we’re scared sh*tless of) the feeling of disappointment or rejection.

Dating is hard because it's vulnerable. Our emotions are involved and it's almost inevitable that we get hurt. But avoiding hurt isn't the goal of dating, finding connection is. And much like baseball, we just have to accept that we'll have a few strikes and foul balls in search of a home run.

But if we live our lives focused on minimizing strikes, the most effective tactic is to never swing at the ball. And then we sit around and wonder why we haven't hit a home run yet? There has to be risk in order to get what we're looking for.


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