Ask A Dude: I’m Too Shy To Flirt

[Got a Dude itch you just can’t scratch? Sick of getting the pity-eyes as you sift through the Self-Help section at your campus bookstore? Over wondering what those boys are thinking?  We got your back, girlfriend. Send your question over to The Dude won’t sugarcoat it, beat around the bush, or any other weird cliche that means lie to you. Like a nice, juicy hot dog, he’ll be 100% real beef, 100% of the time.  So bring it on, ladies.]

Dear Dude,
Without sounding conceited, I’m smart, funny, pretty and I’ve got an hourglass figure. My problem is that I’ve got a whole lot of personality and apparently I’m intimidating to guys. Whenever I go to parties, I get hit on but it never goes anywhere because although I act really outgoing, I’m secretly shy when it comes to guys and, ironically, I am attracted to guys who are also shy.

None of my friends would believe it, but I can’t for the life of me ever think of what to say to a guy. I’ve tried visualizing them as girls, but it never works, I just can’t get comfortable around them. Part of my problem is that my best friend, who I’ve known since I was a kid, is gay, but I didn’t figure that out until recently. When we hang out together, it’s like we’re two girls. Now every time I’m with a guy, I expect it to be the same level of ease, but it never is. Even with my guy friends, I’m not at ease and would never call them to hang out alone.

Can you think of anything to help me out? I’m getting desperate here.

Tongue Tied.

P.S. I always find out their interests and steer the conversation onto that topic, but I still can’t seem to make anything of the flirtatious encounters. 

Dear Tongue Tied,

Shyness is a debilitating condition. I’ve been a recovering SST (shy silent type) my entire life. Fear not though all you fellow sufferers, there is a cure.

Confidence is key Starting the conversation is the scariest part of the process. We’re terrified of rejection. We feel like we have nothing to contribute. Part of the fuel for shyness is the fear of disapproval. We want to be accepted. Acceptance is approval. Has the chain of logic belted you upside the head yet? To combat the panic attacks, you have to take the pressure off of yourself and look at the situation with a little perspective: “If he/she throws a slushy in my face I’m not going to die, I’m not going to be suddenly rendered mute, I’m not going to run out of people in the world to talk to, and I’ll know this person is a dJ*©#e not worth my time.” If you relax, he’ll relax. Deep breaths, ignore the ringing in your ears, and just say “hi.” You’ve got nothing to lose! Fortunately, Tongue Tied, sounds like you’re already past this stage of rehabilitation. Onward…

How do you get to Carnegie Hall? Practice, practice, practice! Start up a conversation with everyone (unless he has a John Holmes mustache or is wearing a 70’s disco shirt. If he has both and is paler than Sheamus from the WWE, then seek out the Slayer immediately). Conversation is a skill that has to be developed. You’ll feel embarrassed at first but you’ll find your rhythm. Ask any aspiring artist you know, they’ll explain from painful experience that to survive and thrive you have to thicken your hide to rejection.

One of the things that the painfully shy are prone to do is overcompensate. We go from a vow of silence to rambling like Bob Dylan on Adderall. This can be completely unconscious (to you, not to the other person looking for an escape hatch). By taking over the conversation we come on too strong. This turns people off. Ask questions. When you offer opinions make sure you leave room for discussion. Let him be the leader for a while. The next guy you chat up, gauge if you’re intensity can stand to be dropped a few levels.

A pretty, smart, sexy, funny woman isn’t something guys want to run away from. My intuitive inference is that the problem you’re having is your approach due to your shyness, which stems from years of reinforced fear of rejection. You’ve got to take the pressure off yourself to impress. You’re goal shouldn’t be to “win him over” or “convince” him you’re who he wants. That’s putting your self-worth in his actions and belittling all you’ve got to offer which sounds like A LOT. Remove expectations of approval. Focus on having a good time getting to know him because he interests you. If you approach him relaxed then that will set the tone for everything else.

Next time think: you’re not being graded, he can’t hurt you unless you give him the power to, and there’s always the cute guy that just walked in.

Don’t freak out,
The Inter-Dude



  1. chelsea says:

    i needed this. thanks!

  2. d says:

    wow that was very helpful advice, thank you very much dude

  3. K says:

    good advice, and good Buffy reference

  4. J says:

    Tongue Tied,

    I thought I'd share a little male perspective for you. For starters, I'm not a particularly shy person, insofar as I can/will talk to almost anyone. With that said, I'm relationship shy. Generally speaking, I've had nothing but bad experiences with women. I also rarely talk about myself, until I become very comfortable with someone. Fortunately, most people love to talk about themselves, their lives, etc. It is great to ask questions and engage the other person in conversation about themselves. It is nearly impossible to be rejected by someone when you're talking about them, I mean, what would the basis of the rejection be? If you want to be flirty do little things like touch their arm/hand. That is very easy, and definitely a turn on. That and talking to them about them is a surefire way to short-term success.

  5. Ashleigh says:

    This was great, particularly the part about over-compensating. I'm a recovering SST as well, and now it seems like I just blurt things out which are funny in my head but, oh whoops, turns out they're not, which just makes me and everyone around me feel awkward. Colleges need to offer a class in how to behave in social situations.

  6. Karissa says:

    Wow, I feel like I wrote that email, because I am exactly the same. Thanks for the advice!

  7. Emily says:

    Really nice and helpful advice!

    But fyi… you're = you are. your = possessive :)

  8. holly says:

    loved the bob dylan on adderall analogy hehe

  9. cio says:

    love the buffy reference

  10. Renee says:

    Its soo much eaiser said than done. Honestly I walk through places looking down giving off stay away vibes. And I know I do because I'm so imitated by guys in my head I'm literally going please "don't look at me". Its so sad

  11. Kurt says:

    Why do women automatically assume that guys are "intimated" by them if they aren't asking them out? A lot of guys want a woman to show at least a little bit of interest before they ask them out. However, if a woman is so shy that she doesn't show any noticeable interest, a lot of guys will assume that the woman isn't interested – that doesn't mean that the guys are intimidated. If anything, a woman like that is probably intimidated herself.

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