8 Times Playing It Cool Will Totally Screw You Over

“Playing it cool” in the dating sphere doesn’t do you any favors when what the moment calls for is real communication — that is, being direct instead of being subtle, or taking a chance rather than playing it safe. If you’re often unsure what to do, or if you’re doubting yourself, just know that playing it cool is probably going to work against you, especially in these situations:

  1. When you’re doing it… and it’s not working. It’s easy to get into the habit of playing it cool because it’s safe and because that’s what we’re told to do. But it doesn’t always work, and at the end of the day, the reason it often doesn’t is because “playing it cool” and “getting noticed” are pretty much opposite goals. Basically, it might be time to try a different approach.
  2. When you generally get an intimate vibe. You know when you talk to a guy and your intuition gives you the sense that he’s not interested in judging you, or that he’s not one to tell a bunch of other people every detail of what happens in his love life in a particularly egotistical way? That’s when you should trust yourself (and him) and put yourself out there.
  3. When the person you’re into is super extroverted and outgoing… and you’re not. If you’re one to keep to yourself and the guy you’re into is clearly not, trying to stay subtle won’t help you attract his attention if you have the sense that he hasn’t already caught on to your subtle cues. If he tends to “go big” on, say, his social media, the way he conducts himself in public, etc., chances are, he may need a bit of a stronger nudge to notice you if he hasn’t already.
  4. When he’s already given you a green light. Getting a signal is your open invitation to reciprocate. If he’s asked you a ton of questions, gone out of his way to touch you, spend time with you, and make contact in a way that you noticed, then trust yourself. Flirting is all about a give and take. There comes a time when holding back sends mixed messages.
  5. When you’re thinking about it too much. Sometimes you need to just take action and see how it plays out, and then you can put your thoughts to rest and have a clearer sense of your next steps. Getting too in your head about a guy makes things so much more difficult. People become ideas in our heads. Ideas are complicated, and can be intimidating and mystifying. It’s really not that serious.
  6. When you actually know a guy really well and have just realized you actually like him. If you’ve been friends (or neighbors, or co-workers, whatever), for years – or, even if it feels like years, but you’ve got the kind of relationship where you’ve told each other deep stuff and confided in each other and then you have a Cher moment like in Clueless when she’s like, “Oh my god! I totally love Josh!” — then, no, you certainly don’t need to play it cool with him. In fact, you’re probably just feeling awkward and understanding your feelings and unsure how to proceed at this point. So, focus on working out your own feelings and best responses – just don’t put pressure on yourself to “play games” to attract attention.
  7. When you want to know where you stand. If you really like a guy and you want to see if the feeling is mutual, especially if you’re thinking about it all the time and it’s distracting you from your life to the point where it’s way more work to NOT make a move, then do it. Sometimes you just have to bite the bullet. We always regret the things we don’t do, not the things we do, right?