Playing It Cool Isn’t Cool Anymore

"So how long are you guys gonna wait to call your babies?"

I was back home on my first summer break in college when I met Amy. I was 18 years old, rushing around the mall trying to find a gift for my newborn cousin. Amy was a kind-hearted brunette, willing to help a flustered (and charming) stranger find a gift for a five-day-old baby girl. I insisted that she give me a chance to repay her kindness, so she gave me her number.

When I got to my uncle’s house that Saturday afternoon, I was happy to tell my family about the cute girl who had helped me pick out the gift I’d brought. Almost immediately, the question was asked, “So how long are you going to wait to call her?”

My uncle chimed in, as if on cue, “Tuesday, Dan.”

I immediately agreed, telling my younger cousins, “Uncle Mike’s right–gotta play it cool at first.” And I believed this.

This was 1999. Amy had written her number down on the back of my Babies-R-Us receipt. She hadn’t entered it into my cell phone, because neither of us had a cell phone. My cousins didn’t ask me when I would text her, because “texting” wasn’t even a verb yet. When I decided I was going to pick up the phone and call Amy, I literally picked up the house phone, dialed a (1) before her area code, and hoped that she would be the one to pick up on the other end. This really wasn’t that long ago.

On that Tuesday when I finally did call, I gently reminded Amy who I was, and she definitely remembered me. We went out a few times before realizing that we had very little in common besides dark hair and newborn cousins, and we amicably decided to go our separate ways.

Fast-forward to 2005.

I had just broken up with my college girlfriend of four years and was now a man of sophistication. I had two college degrees, my own apartment, and a wealth of sexual experience garnered from two college campuses and a four-year committed relationship. I was, in a word, capital-T Trouble.

That’s when I met Christine. We were waiting in the deli line of Shop-Rite, and we realized that we knew many of the same people. This time, there was no pen-scrawled receipt. Christine entered her number into my cell phone. I graciously accepted and thought to myself, “Gotta play it cool. Three days.” And I still believed this.

What I didn’t want to believe was that I had been out of the game for too long. I was driving home from work when I called Christine on that Wednesday, and it went to her voicemail. I put on my slickest cool-guy voice and said something like, “Hey, it’s Dan–give me a call when you get this.”

Three hours later, I got a text message saying simply, “WHO IS THIS??”


Undeterred, I immediately pushed “send” on my cell phone to give her a call. When her voicemail picked up again, I suspected something had gone awry. Three more calls over the next 24 hours confirmed another thing I didn’t want to believe: she was avoiding me.

The moral of my story? Playing it cool doesn’t work anymore. Playing it cool used to mean that I was too busy to get to the phone or had too much going on during a particular day to call a girl back. I would say things like, “I was helping my brother move furniture,” or “I had a lacrosse game down the shore.”

And these were perfectly reasonable excuses for me not to call. After all, who could get to a phone under those circumstances?

Not anymore. Now I can log on to three different websites before I even get out of bed in the morning. By the time I sit at my desk to start work, I’ve read more than 30 emails and responded to probably half of them. I get texts from friends in England, Canada, and California just seconds after they’ve hit “send.” If I were still on Facebook, I could probably tell you what three of my friends ate for breakfast on any given morning.

There is no such thing as downtime anymore. Today, we are always connected, we are always plugged in, we are always able to reach out and touch someone. And that also means that we have no excuses not to be in touch with potential love interests.

Playing it cool has become too obvious for what it really is: a contrived attempt to be aloof.

Uncle Mike might not agree, but now, when I meet a girl and get her number, I text her the next day. Nothing big–just something intentionally short and funny to get a response. If I happen to get lucky and sleep with a girl, she’ll get a phone call within 24 hours. Again, nothing big–just a quick, light conversation that may or may not serve as a little reassurance that she’s not a ho for banging me.

Of course, I don’t need to smother a girl, either. When I first meet someone, I have a strict one text/call per day policy. Playing it cool might have worked once upon a time, but I’m pretty sure being annoyingly needy has never been cool.

Not that I would know from experience or anything….

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  • Thanks for sharing, Daniel. I appreciate learning about your paradigm shift.

    It reminds me of the part in the movie “He’s Just Not That Into You” when a guy tells Gigi he might not call for a while because he’s going to be out of town. Then she calls her guy friend to ask about it and he says something like, “Where’s he going? Somewhere where they don’t have phones?”

    There is, however, something in here that you mentioned twice that bugged me. Having a girl put her number in your phone. I don’t like it.

    If a guy handed me his phone and asked me to put my number in it I would hand the phone back to him. Depending on the circumstances I would either make him enter it himself or just walk away. Something about that says cocky bastard to me. (Not that I think you are a cocky bastard — at ALL.)

    At the very least it’s kind of lazy and a little rude. I don’t know how your phone works and I don’t want to have to learn just to get you to give me a call.

    What do you think? Am I being a princess?

    How about the rest of you ladies — do you have an opinion on this?

    • Well, it might depend on how loud the venue is. I know I’ve handed my phone to a girl before, but that’s because I could barely hear anything she said….

    • I don’t enter my phone number. If he wants, I will tell him and he can call my cell at the same time so we have each other’s numbers.
      And yes. If a guy isn’t calling, he isn’t into you.

    • Well, I intentionally have a dumb (non-smart) phone, so if the girl can’t figure out “how [my] phone works,” when I hand it to her, then I probably don’t want her number anyway.

      In all honesty, most of the time I just give the girl my phone number and tell her to call my phone right there. That way we both have each other’s info, and I’m sure I am correctly spelling “Kristen” with an E instead of an I.

      I’ve got pretty thick skin though, Crystal. Feel free to call me out on any of my cocky bastard behaviors- believe me, I probably deserve it.

    • @Danny

      “Smart” phones are actually easier to use, in my experience. Most people can pick up an iPhone and work it, even if they’ve never used a smart phone before. Touch screens are intuitive. Whereas most people (including me) can’t do that with regular cell phones.

  • I think maybe you are lucky that the communication age has ruined your game! The 3 day rule never made sense to me- if a girl likes you, she wants you to call right away. I always felt that if a guy was into me, he wouldn’t be able to wait the requisite 3 days to talk to me again!

    I really want to know why guys are so obsessed with not looking too interested? Are you afraid of giving us the upper hand? Of scaring us away with your desperation?
    If we’re not interested, it doesn’t matter how cool you play it. But if we are interested, playing it too cool can be a turn off!

    • I think it’s just a simple way of not coming across as too needy. Sometimes, if we really like someone, we may end up coming off as too eager, and that could scare the other person away.

      Of course, you’re right. If the other person really likes us, then we might not have to “play it cool” in the first place.

    • Guys don’t want to look too interested for the same reason girls don’t want to put out on the first date. It plays on tired and stereotypical gender expectations (boys give love to get sex, and girls give sex to get love), but if this article is any indication, hopefully those expecations and roles are changing for the better.

    • I dunno. All a guy is telling me when he doesn’t call right away is that he’s got something better he wants to try out first. Makes a girl feel like a consolation prize!
      But, hey, if ending the 3 day rule changes our stereotypical gender expectations, who am I to argue?!

  • The three day rule never worked for me when I was dating, but then I was in prime pick up location when I was single and attractive. Right across from a hospital at a Deli. Guys came up to the counter and asked me out. Calling me might not have worked at all back then (1999!), because I worked 65+ hour weeks. Dates were on my lunch and dinner breaks only. I honestly thought that if he waited three days to call me then he wasn’t interested at all.

    The hubby broke all the rules. He never asked me out on a date (too shy) or to marry (we just always talked about it and finally set a date.) When I met him we hung out as friends until we both realized we should date.

    Loved the article by the way. Well written and interesting.

  • Heh, I had a cellphone in 1999.

    I never liked the whole three-day rule thing, and used to call the next day when I liked a girl. Of course, I always got shot down. After more than a decade of rejection, I didn’t try to play aloof. I became aloof. Now I don’t call at all. If she likes me, she can call me.

    • Whoa. Now that’s aloof. 😉

      You know, I used to be like that when I was in college, but it was more out of shyness than anything else. I pretty much only went out with girls who would make the first move, because my own first moves were way too awkward to ever be effective.

      But then, I realized that in doing so, I was effectively shutting out a large subset of the female population: namely, girls with less dominant personalities and who may have been on the shy side themselves. And some of them might even have liked me, too. They just played more into traditional gender roles, if you will, and would never–or didn’t know how to–make the first move.

      Anyway, I’m not saying that what you’re doing is bad. If it works for you, awesome. I just feel like you might be missing out on the chance to date some cool women out there….

    • In 1997, I asked my father to help me buy my first car as a birthday gift. Instead, he got me a beeper. 24 hours after I got it, I had lost it.

      I didn’t get a cell-phone until I was 21.

  • Yeah, it seems that the women who are aggressive enough to make the first move mistake my inaction for a passive personality. And the kind of women I am attracted to are generally less aggressive/dominant. The thing is, I used to try to date those women and never got anywhere anyway.

    Maybe I am cutting them out of my dating pool, but the nice thing about being aloof is that I don’t care anymore.

    • And the kind of women I am attracted to are generally less aggressive/dominant.

      Yeah, see, that’s why I responded. From what you’ve talked about or hinted at in the past, I would’ve thought you to be more into the less aggressive women.


      …the nice thing about being aloof is that I don’t care anymore.

      Fair enough. 🙂

  • Hey, I have a random question for the commenters who don’t have an account registered with the site:

    Are you able to edit your comments now? I downloaded a plugin that’s supposed to let you edit your comments within 30 minutes of posting it, as long as it’s from the same IP address. Just wanted to see if it actually works or not….

  • Then why didn’t you call me the next day, Danny? 🙁

    Honestly, this is something I’ve never really had to worry about. It’s probably mostly due to age and my (HUGE) inexperience when it comes to casually dating, so I don’t really know how I’d react. I do have a friend who ALWAYS makes the guys make the first move though. She has rules on when she can/will talk to a guy, she refuses to call or text them first, ask them on a date, kiss them first, ANYTHING. She had this horrible trend of attracting completely clingy creepers who wouldn’t ever leave her alone after she showed disinterest. I think most guys weren’t comfortable doing all the work without any reciprocation or seeing any interest from her, and so it was only the clingy psychos who would pursue anything.

    I told her as much, and she changed her philosophy a little bit, and now things are looking up. So, in summation, playing it cool and trying to seem disinterested may attract the wrong crowd.

    • I didn’t call because I knew I was too young for you, dollface. Please accept my apology- I didn’t want to subject myself to the heartbreak of losing you to a guy who’s my Uncle Mike’s age.

  • I blame Steve Jobs. I don’t know why—I just do.

  • I thought this was a great article. I really appreciate when guys are just upfront about being into me, it makes it easier for me to reciprocate affection rather than trying to figure out the rules of each particular dating game.

  • Good article! I don’t have a lot of experience dating “formally” but if a guy doesn’t call me the day after then I assume he isn’t interested and basically write him off! Not that I always wait for the guy to make the first move though :p

  • Dating is definitely a different “beast” than it was back in the day. Is it sad that the 90’s are now referenced as “back in the day”! Good article either way. Nice to know you’re changing with the times, DB.

  • I think you’re right about this. I wouldn’t want a guy to wait three days to call me. And actually, it’s easier to text-chat back and forth first than for him to call right away, so I recommend doing that first.

  • I am the biggest ANTI Text message person going. I have no issues with guys asking for a girls number – mine especially BUT if you feel the need to send me a text I will not be a happy bunny. As far as Im concerned sending a text message requires no amount of thought at all, AND it can be done at any time – For all we know you male species could be sending us a text message while you are parked up in the gents or as i have actually discovered before about a guy that took interest was he was texting me whilst he was with another girl!!!.
    For a MAN to call a girl this requires them to take time out of whatever they are doing and to also focus on the conversation at hand. Any man that calls me always immediately gets browning points because I know they have actually made the time to do so.
    Please note this does not include the occasional 2am booty call.

    • You’re right- text messages are kind of mindless and easy to do. But then again, that’s kind of the point.

      When I’m figuring out how I feel about a girl, text messages suit my purposes. If I’m not sure about her yet, I’m not going to call her and let her think that I’m completely interested. It’s false advertising, and it sends the wrong message. I’ve always found honesty to be the best policy- if I’m honestly not sure about her yet, I’m not going to pretend to be into her just so I can see her again.

      It’s almost like a end-of-the-first-date kiss. A phone call is a full-on open mouth kiss, while a text message is one of those “did our lips just touch?” peck on the side of the mouth/cheek. Generally I like to roll the dice and go for the open mouth kiss, but unless I’m sure that I really want to kiss this girl, she’s going to have to settle for the peck on the cheek.

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  • Better to project your feelings and risk rejection than to sit on the fence and get left behind. If she’s into it she’ll reply right away and if not, why then, she’s just not. No harm no foul. I never understood playing mind games but then, I’ve never really “dated” either. As a rule, if it feels right go with it seems to work for me. Then if it flows it also feels right. Probably not the best way to find a mate tho – leaves a lot of room for making really stupid mistakes. Once an attachment develops, it’s much harder to be cruel to another even if it’s in my own best interest to do so. Perhaps that’s partly what leads to “making it work for the sake of the children”

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