Is There Such A Thing as Playing Too Hard To Get? Ask A Pro

By The Head Pro

Send Head Pro your questions about life, love and twitter sex to [email protected]


5 months ago my ex of 3 years and I broke up. It was a really peaceful break up but still hard bc we were so close. I decided to do something wild and crazy and DMd a pic of my face to this celeb and said hi.  He ended up writing back and I was totally floored.  I never thought he would respond so instead of playing it cool I went on an all out campaign and we had a fling which was amazing.  We've hung 3 or 4 times at his house and he finally ( I say finally bc I asked for it and realized that that might seem weird as he has no clue who I was) gave me his now we've been texting.

My question is...since I was the aggressor...did I lose my upper hand?  We've had great chats and I haven't pressed him for anything but I also will only have standard sex and he wants more and I also won’t hook up at leave...I like to stay over and get up in the morning and leave. I feel like hes a little bit intrigued bc I dont just do everything he wants.  The problem is I kinda like him now.

What should I do to turn this into more than a fling?

Thank you!


I don’t think I totally get what’s going on here. So, like, you DM’d a pic of your face to a rando celebrity (which I didn’t even think you could do without them following you), and then you started fucking, but you’re just now getting his phone number? And you think that, somehow, hanging around longer than he wants you to somehow endears you to him? Honestly I don’t believe any of this for a moment, but then again I don’t know why anyone would go so far as to make up such a stupid-sounding story for no reason.

Anywho, I don’t know why you’re so quick to label this a “fling.” Yes, your relationship began under less than romantic circumstances, but now you hang out, hook up and talk often. That sounds more like a fuck buddy than a fling, which brings to mind a very brief yet intense sexual relationship. As to how you convert a fuck buddy you aggressively pursued on twitter who also wants to do butt stuff into a boyfriend, there’s not a lot you can do. Normally you’d want to force the issue by spending time during the day in non-sexual situations, but if the guy’s really famous, it’s a HUGE commitment on his part to be seen dating someone in public. The best thing you can do is to stay the course, continue to play by your rules and see if you can gradually get him to agree to expand the relationship as you earn his trust.

I should be more active on twitter,

Head Pro

Hi Head Pro!

I need some advice. I’ve hooked up with this guy a handful of times and am starting to develop some feelings for him. (Hence, me spending x amount of time writing this email to ask for advice). This guy is the type that is super attracted to bold and confident girls. I’m a big believer in the guy being the one to pursue the girl because call me old fashioned but if he wants it bad enough he would, right?? So I’ve been playing hard to get like its my job but he doesn’t really make that big of an effort with me anyways. Normally I would classify that as a “he’s just not that into you” situation but this Friday my friend was talking to him at a party and he asked about me and she asked him why he hadn’t approached me at the party. He responded with, “Well she doesn’t really respond to my texts/snapchats so I don’t really think she’s interested in me.” My friend responded that she doesn’t necessarily think that’s true but that I just like to play hard to get and be pursued. He goes back, “well I play hard to get too.”

Is it really possible that two people can game play this hard core with each other, or was his response just a cop out and he’s really not that into me?

Give it to me straight up!

Serial Gamer

Dear Serial Gamer,

Jesus, where to start? First, it’s intellectually dishonest to fuck a guy a few times and call yourself “old-fashioned.” Second, you seem to have a very fundamental misunderstanding of what it means to “play hard to get.” For instance, in no way does “playing hard to get” or “being old-fashioned” conflict with being bold or confident. It also doesn’t particularly describe the situation you’ve found yourself in, where you hooked up with a guy and then decided there was something to be gained by ignoring all of his attempts to contact you.

“Playing hard to get,” for the uninitiated (and we are initiated, aren’t we Serial Gamer?), describes the means by which you keep someone on the line. It’s the push/pull, the give and take that occurs in a fledgling relationship (and even a mature one, if you know what’s up). It’s communicating pleasantly with someone, but not agreeing to go out on a date just yet. It’s dating someone casually, but not being DTF right away. Basically, it’s creating positive experiences and reinforcement for someone, but leaving them wanting a little more each time until they’re sufficiently invested in you as a person. It behooves both men and women to do this.

Guys view intimacy as linear, also known as the “escalation ladder” in creepy PUA-type circles. First comes interest, then dating, then kissing, then sex, etc. Basic “sex as a baseball analogy” stuff. It theoretically works in reverse, too - if a girl will sleep with you, then she’ll probably go on a date with you, too. By doing one but not the other, you’re completely fucking with his whole paradigm. When his dataset consists of a handful of hookups and a bunch of unanswered texts, his only conclusion is that he was wrong, you weren’t really that into him and it was just a fling.

It’s not an issue of you both playing the game too hard as it is you trying too hard to play the game incorrectly. If you like the guy, you kind of have to work with him if you want him to know you’re open to being pursued. Not that hard.

Elusive kisses,

Head Pro

Send Head Pro your questions about life, love and twitter sex to [email protected]




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