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Why "Playing it Cool" is a Mistake

Updated: May 26, 2023

This article is about a big dating mistake which is playing it cool. Have you played it cool when you've gone dating? To explain what playing cool means: It's an attitude - It's really about being as casual to the point of not wanting to reveal your hand too early and it's usually come about because of a bad experience that you've had, where you feel like when they were perhaps more revealing, had your heart on your sleeve and, as a result, got burned.

Why playing it cool ruins dates, relationships and sex

This attitude of playing a call manifests itself in a few ways. For example, the behavior can be in our texting where, for instance, you might be seeing someone who you really like. And that person might be messaging you on Instagram and says, "Hey, I really liked that photo of where you guys are at." You might reply, "Yeah, it's a really great place nearby my local town. I'm glad you like it," and they reply, "LOL." That's an example of playing it cool because rather than being like, "yeah, look, I'd really like to check it out with you at some point, I've been meaning to go there," They're defaulting to a very casual remark, with the assumption that it will actually drive you to be more interested in trying to follow up with further messages. And on that note, with regards to texting, you might often find that this person is playing hot and cold. Rather than having consistent messages, you always feel like you're putting in more effort with the person who's playing it cool. It feels like they just want to not show their hand in telling you how they really feel. People who play it cool usually do like you but they're just afraid to actually say it to your face because they're worried that they'll get burned again.

This can impact the way in which we date others as well. We can sometimes be overly friendly without wanting to get too touchy feely or too intimate or romantic. The reason people do this is because they're so scared of allowing their feelings to be felt that it can even detrimentally impact their sex as well. If you're in a situation where you're sleeping with someone, and they kind of feel like they're holding back emotionally, they're playing it cool because they don't want to get hurt.

Why playing it cool backfires on you both

Ultimately, playing it cool hurts because that person is afraid to love and is afraid to get burned or is afraid to be vulnerable with their partner. This also manifests itself very early in the dating cycle, when within the first couple of days, you might say, "Where do you see this going," and they might be like, "Oh, I don't have an agenda. Let's just go with the flow. Let's just be cool about it." That might sound alright, in theory, because to many of us, we may think to ourselves: I'm not really ready to settle down yet. I don't really feel like I'm ready to be with a partner yet. That thought is totally fine in the moment. However, your body might have a very different reaction when you're in that moment. If you allow the other person to have this attitude of playing it cool then you're both doing a disservice to each other because you're not actually being honest with your feelings.

To allow any form of relationship, including friends-with-benefits, you need to be 100% transparent about how you feel for another person at all times. The reason that friends-with-benefits is so strict on this is because the minute feelings are introduced, you've got a lover and a friend. That is not a friends-with-benefits relationship. If you want to be in a relationship, you both need to be comfortable with your feelings. And if one of you is withdrawing due to fear then you've really got to ask the question: how long are you going to wait for this person?

So you come up to a situation where both partners have reached a zero sum game, they cannot get to where they want to be. And it's because there's fear and there's also withholding of one's emotions involved. Ultimately, this is the reason why playing it cool is so detrimental to the impact of a relationship.

The better approach to playing it cool

I recommend an alternative to playing a call which is be radically honest. Just talk about what you want, what you're looking for, and understanding the kind of relationship that you're going into. I want to make it clear that there is a difference between being needy and being direct. When meeting someone, the clearer you are about the kind of experience that you're after you get an understanding as to where you would like to find yourself in the near distant future. Because if it is a relationship, better to state that to a person now and let them freak out at the beginning because then you'll know that that person probably wasn't worth the time and effort in the long run, rather than four weeks down the line where you could potentially be heartbroken for thinking that there was something worth there at all.

So ultimately playing it cool is actually a time waster compared with having a direct conversation at the start of the dating cycle, just saying,

"hey, look, you know, this is what I'm looking for down the road, doesn't mean that I have to be with you. But I'm just curious to know where you're going with this."

And you can phrase it however you like. The point is: be clear about what you want, be understanding as to the kind of experience that you're after and you'll find that you'll actually end up with a lot more clarity from the other person's side, rather than trying to control them with this whole attitude of not revealing your feelings.

More often than not, people will react to playing it cool by withdrawing, getting bored, feeling indifferent towards you, and ultimately back off because they don't feel that you're actually showing any signs of attention for them, even if you really like them. That's why playing it cool is detrimental to dating.

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