Does Being Shy Hurt My Chances With Guys? Ask A Pro

By The Head Pro

Dear Head Pro,

Your latest Propinion piece on Katie Heaney brought up a question that's been lingering in the back of my mind for a while. So, I've always been a reserved girl. I definitely love going out, having fun, and being social but it takes a while for me feel comfortable with new people and I've been described as "quiet" at times. And I'm wondering - is this aspect of my personality hindering my chances with guys? I've dated and hooked up, but I've never had a serious relationship. And I really want a relationship! (I feel like you're going to say something like you can't make a relationship happen just because you want it to, but it is frustrating).

I know I'm not ugly, or at least I know girls who are about the same/less attractive but are constantly going on dates, hooking up, getting boyfriends, etc. I've always been under the impression that guys will make it really obvious if they want to date you (or even just fuck you) so I generally let them make the first move/subsequent moves because I don't want to be rejected or feel too hurt if they lose interest. But should I be more proactive (and how)? Could I be giving off a standoffish vibe because I'm quiet? Do you think guys tend not to go for quiet girls as much in general?

Thanks Head Pro!

Quiet girl

Dear Quiet Girl,

Well, obviously this email is a couple of weeks old, because my Propinion from last week resulted in more hatred and useless straw-men than a hay bale maze at a Klan rally. This, thankfully, is a much quieter (haha) issue. You are correct, you can’t just “make” a relationship happen, but that doesn’t mean you aren’t entitled to the desire to have one. I’m kind of surprised to hear it’s an issue, because quietness/shyness has traditionally been seen as a desirable, “feminine” trait in women. Maybe the times, they finally are a-changin.

I think we’re dealing with a couple of possibilities. The simplest one is you are literally the shyest person on Earth. In that case, what comes across (in your eyes) as “letting them make the first move” might actually be you covering your face with your hands before running away screaming at the first sign of contact. That would probably hurt your chances, a little bit.

Since your problem isn’t so much with getting laid or meeting guys but with maintaining relationships, I have a feeling what’s happening is that guys are mistaking your quietness for being boring, or a doormat. No one, guy or girl, wants to date anyone who can be walked all over. The solution is easy (at least in theory): Start expressing yourself more. Have opinions, and voice them. That doesn’t mean going from being a shy girl to an obnoxious one. It just means that if someone asks where you’d like to go or what you’d like to do, have an answer other than “I don’t know, whatever you want is fine.” That shit gets old in a hurry.

Sure, a lot of guys will look to the easiest option when it comes to hooking up, but everyone wants to be challenged by the person they’re dating. If your default setting is to hang back or defer to others when hanging out or making plans, maybe keep that in mind and work on making the things you do say count for more over time.

Quiet kisses,

Head Pro

Dear Head Pro,

Where to even begin. I met a guy during orientation of my freshman year and my first thought was literally "aw what a nice little virgin". I went into college dating my high school boyfriend (lol), so my relationship with this guy was strictly platonic... for about a month, until we drunkenly fucked in an academic building. We high fived when it was over and I honestly thought the situation was hilarious. I didn't tell anyone about us, and we didn't really start consistently hooking up until about a month later. My girl friends thought he was so attractive, and since we spent so much time together everyone thought we were dating. But, for whatever reason, I made such desperate attempts to prove everyone wrong. I would go out and hook up with other people and told this guy that whenever we hooked up he had to keep it a secret. I really wasn't into him when I first met him, but through random sex and the fact that we hung out every day (I'm talking eating together at every meal and watching the entire series of 24 in one semester), I developed feelings for the guy. But, being stubborn and wanting to prove something, I never let him know and blew him off the entire winter break. We got back to school for spring semester and he had been talking to another girl, and they ended up dating.

Fast forward to last summer. He and this girl had broken up and I was spending a good portion of my summer in France. He would message me constantly asking how I was and updating me on his summer, and as soon as I got home we started hooking up again (we're both from the same area in Maine). We got back to school though and he rushed a fraternity and basically wanted no commitment with me, but still kept me around. He would tell me how in love with me he is, how he thinks we're going to end up married, etc. etc, but didn't want to date me. Now, we're in spring semester, and after several ups and downs he just doesn't want any intimacy with me anymore, because of how dramatic everything had become. But he says he still loves me and wants something to work out down the road, and takes back none of the things that he said. What the fuck? I mean we have great sex but what the actual fuck. I wasn't the bitch that brought up marriage, he did. And now I suddenly don't matter? He told me he wants to stop holding me back and let me experience college and find someone better suited for me right now. I'm so scared that we're just going to disappear from each other's lives all together and that I'm going to become irrelevant to him.

Does he actually have feelings for me? I can't move on because I love him too, what's my next move? I'm so confused.

I actually miss him a lot.


What in the actual fuck? Read that again - it sounds like it first and second halves were written by two different people. Look, we all like to think of ourselves as the protagonist in our own love story. What you find out, though, is that in real life when the asshole leading character sees the error of their ways and goes after the love interest, no one’s around to give a fuck. Ask any super cool former frat star who tries to connect with former classmates after graduation.

You spent an entire year fucking with this guy. Even worse, you spent an entire year doing the things that men are told indicates that a woman’s interested in him (the sex stuff), yet you pulled a fucking Judas on him any time anyone asked about it. That’s horrible. Sure, guys are famous for pumping and dumping girls, but even halfway decent guys will at least own up to having been involved with you. Yeah, some guys will pull the same shit you did. It’s not cool then, either.

He rushed his fraternity and all of a sudden, he has options. It’s like the plot to a bad romcom, only somehow less interesting. I can’t say for sure why he’s repeatedly so insistent about saying he loves you or sees a future with you, but it’s probably a combination of remnant feelings and not knowing what to do about this girl who’s all of a sudden so into him. The rest of it, the talk about not wanting to “hold you back,” is standard bullshit rhetoric people use when they want to keep fucking you but don’t want to be otherwise accountable to you. Kind of like what you were doing last year!

I don’t really have any advice for you, other than that over time, you might be surprised to find that you don’t like who he becomes. Think about it: Even though you pulled the same shit on him earlier, are you really down with hitching your wagon to a guy who says to your face “maybe later, but right now I got other bitches to fuck?”

Sophomore year isn’t exactly the best time to take future marriage talk seriously, anyway,

Head Pro




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