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I’m A Dating Coach & This Is The Most Common Dating Mistake I See

The power of a little healthy pessimism in dating.

There are too many unknowns in the beginning stages of dating to get caught up in being right about someone. It’s actually a setup for disappointment and can put a huge damper on your energy.

Take my client Jia. They were so down on themself each time a person wasn’t a match that they believed they had terrible instincts and would be perpetually single.

“I guess I’m just really pessimistic,” they said.

Here’s what I told them: “Believing you’re never going to find someone is fatalistic, not pessimistic. A healthy dose of pessimism can actually be really helpful when dating! Being pessimistic means that you don’t expect things or people to be perfect and that you anticipate some amount of disappointment.” I then went on to explain how pessimism can buffer you from unrealistic expectations and can help make the process smoother and more fun.

There’s no such thing as the perfect match, but there are plenty of “good enough” matches that come with their own unique challenges. Think about it: the world is too big for you to not find folks with whom you’ll connect. Whether you’re looking for a relationship, sex, or both, other people are looking for something similar. You just have to find each other and stay open to what less-than-ideal qualities you each inevitably will have. Every single person, including us, has some imperfect qualities. The trick is finding matches with comparable or compatible flaws.

The unrealistic expectations we carry.

If this is all hitting you too hard, I get it. We receive a lot of messages about partnership that conflict with this idea. Soul mates and “You complete me” and true-love narratives dominate the way we talk about partnership. Not to mention that finding this elusive perfect person is supposed to be easy (“When you know, you know”), but also somehow hard (“Relationships are hard work”), and so worth it (“You can have it all if you just try harder!”).

So often we’re told not to settle, but every relationship dynamic involves settling to some degree. This isn’t necessarily a bad thing, though. There are many instances when people settle in the interest of getting an approximation of what they want, and it’s not seen as a terrible thing. In fact, in pretty much every other aspect of our lives besides dating, it’s expected that we compromise or accept conditions that are less than perfect. We don’t always get the job we want with the pay we need, or if we do, there may be aspects of the job that we hate. Our relationships with friends require a certain amount of settling, as we can’t control when our friends decide to move and we can’t pick their partners for them–we have to accept the fact that their choices aren’t ours. But somehow, in sex and dating we are expected to settle for nothing less than perfection.

Being a little pessimistic about your dating life doesn’t mean you stop looking for people with whom you feel really good. It just means looking at dating as you would any other aspect of life. You will make choices that you think are good in the moment, evaluate how those choices work for you, and then make new choices based on what you’ve learned.

The more you can accept that dating is an imperfect process–and let go of the impossible standards that society has placed on it–the easier it will become. And the easier it is, the happier you will be in the long run with your choices.


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Acknowledging your wins, big or small.

Being pessimistic doesn’t mean being sad and negative all the time either. Expecting that things won’t always be great means that you can better recognize when they are. In fact, your definition of success might even open up, giving you more to celebrate.

One of the ways you can help keep yourself from experiencing dating burnout is to celebrate any wins you experience, big or small. If you leave a first date feeling relatively good, that’s a win. If you leave feeling like you just dodged a bullet, that’s a win. If you get a second date you wanted, that’s a win. And if someone rejects you before the second date, that’s also a win because you are released from thinking that this person is a viable option. When you decide to start dating, celebrate yourself for even trying!

Now take a moment to think of five things you can celebrate. They don’t have to be major accomplishments or even super positive. They could be anything from reading this book to hooking up with someone for the first time to being dumped.

Celebrating the good, the bad, and the ugly of dating allows you to stay grounded for whatever comes your way. It’s a great way to truly embrace the process.

Excerpted and adapted from This is Supposed to Be Fun by Myisha Battle. Published January 24, 2023 by Seal Press, an imprint of The Basic Books Group, a division of Hachette Book Group LLC. Copyright (C) 2023 by Myisha Battle.


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