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Why You Don't Need To Play It Cool On Dates

Written by Almaz Ohene

Have you ever stopped yourself from saying something that you wanted to say to a new match? Or started acting like a different person on a first date? You’re probably doing a lot to appear ‘cool’ in the name of ‘not scaring them away’.

Why do people play it cool on dates?

Some people who play it cool – especially the ones who really lay it on thick – are doing so because they fear rejection. But that’s all part of the dating process. If you don’t put your authentic self out there, and risk a few rejections, you could actually be holding yourself back.

Yes, being ‘cool’ can mean being carefree and having an easy-going attitude, both of which are super valuable traits when it comes to dating. But for the most part, ‘cool’ dating mostly consists of undefined relationships where people aren't communicating what they really want out of the situation.

In reality, you’re probably being untrue to yourself to make yourself seem ‘cooler’, because dating culture can make single people feel bad for having high hopes about finding a partner who could be great. Toxic dating culture can make you edit yourself; taking away your quirkier aspects and replacing them with a more palatable version to get the relationship to the next stage.

Why playing it cool doesn’t work

While dating, there can a lot of fear around appearing too eager (or even desperate) by expressing feelings, which is where the pressure to appear ‘cool’ comes in. When you hold back too much, you become inauthentic and acting ‘cool’ actually means that you’re doing yourself a disservice. When you fake your coolness, you’re wasting not only your time, but your matches’ time too. Your match might go along with it, even though they’re not responding to the real you. When you then end up in a situation where the other person doesn’t truly know you, it can be hard to speak up for what you really want out of fear.

If you’re finding yourself falling into this pattern, you might need to evaluate why you feel the need to be something else. Chances are, there are self-esteem factors at play. A person who’s truly secure in themselves doesn’t feel the need to pretend to be something they’re not. If this resonates, you’re not alone – but it might be a good idea to remember all the reasons someone would be lucky to date the real you.

A note on attachment styles

Playing it ‘cool’ all the time could also mean you attract people who have an avoidant attachment style. These are people who are very self-sufficient and enjoy closeness mostly on their own terms. They like to keep intimacy at bay, and mainly pursue people who seem disinterested. It sounds counter-intuitive, as you’d imagine most people would find comfort in a secure relationship. But for some, the insecurity of not really knowing where a relationship is going feels familiar, and humans are creatures of habit.

If someone has an avoidant attachment style and starts dating someone who’s secure in what they want, it will feel unfamiliar to them, and they will likely bail. The trouble is, if you pretend you’re ‘cool’ about not having labels, you’re going to be an attractive choice for someone who’s not that into commitment.

How to be more authentic when dating

First and foremost, be honest about yourself and what you want on your profile and in conversations. Use recent photos, give your real age and include information about any dependents you might have. If you prefer an activity over meeting up in a bar for a first date, then do mention this when you’re messaging with your matches. If you’re not sure about physical contact in the first few dates, but might consider the possibility once you feel more sure of the connection, then you can absolutely make that known to your matches.

In an effort to be easy going, you might let your match take the lead on dates. It may seem ‘cool’ to let your date decide what film you go and see or where you’d like to go get drinks, but this tactic can also make you seem passive, and even a little disinterested. Instead, let your match know what kinds of things you’re really into, so that the time you spend together is fun for both of you.

If you’re being casual with a friend or acquaintance but want to take things to the next level, it can be scary to be honest about what you want. But if you play it too cool, things may never progress. In this kind of situation, it helps to be assertive and say/or message something like: “Listen, I’m attracted to you, and I know we’re casual, but if we’re going to do this you need to actually date me and give us a real shot”. A statement like this shows them that you value yourself and that you’re confident enough to ask for what you want.

If their response isn’t the one you wanted, you are allowed to let that person go to give yourself more space and time to build a connection with someone who is happy to show their keenness.

Being yourself will enable you to find someone who thinks you’re ‘cool’ without having to put energy and effort into being what you aren’t. It’s from this place of authenticity that you can start to build a relationship based on true connection.

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