Dear Don Cusack – Young Shy Guy

Welcome to the inaugural advice column! Let’s just hope I don’t ruin your lives too bad…

‘Young Shy Guy‘ writes:

I’m not sure if this even counts…

I’m still in high school and there is this specific female that has caught my eye. The main issue is, I don’t know her at all. So any advice on how to actually confront this girl. I see her everyday on campus but we have no connection (not a stalker)… No classes, different lunch, and I’m not sure if we have any mutual friends. (mainly because we are different graduating classes) I think it’s a lot different at a school then at some other location. At a party, movie, club, etc. you can try to holler and if you get shot down it’s no biggie because you may never see that chick again. In school, you see this person constantly and I’m sure you remember all the gossip and the he-say she-say bullshit. The girl tells her friend that this dude tried to holler and it gets around that you failed… Anyways, some information on how to actually talk to this chick would be appreciated.

Also, do you think I should go at her in a friendly tone or a bit more aggressive? In other words, after I eventually talk to her, should I be a “nice/friendly guy” or let her know I’m looking to maybe date? I know there are other fish in the see, yadda yadda yadda. I’ve been living the single life so I’m looking for a little bit more. I’m not trying to get married or anything but I’ve had enough of the games.

Thanks a lot “Don Cusack”.

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First off thanks for being the Guinea Pig! Now let’s get down to business…

Ahh, young love. I remember high school trysts just like it was yesterday. Quite frankly because a good 70% of people still act like they are in high school years after they graduate but that’s a whole nother post. The issue at hand is how to approach this girl without any sort of inroads (no mutual friends, no classes together, different lunches, etc…) and the most immediate solution is to simply approach her.

Since there are no commonalities in this scenario then the only thing to do is man up and let her know that you are interested in getting to know her as a person. Be it AIM, email or phone numbers whatever your most comfortable method of communication is try exchanging that contact with her. That way the conversation is easier for you but in all honesty take what she gives and work with it. Text is cool but be warned: women don’t like that shit when romance is involved. The text messages are made for confirming plans or quick hello’s, not in depth conversations. They lend themselves to miscommunication and more importantly rarely give any shine to your personality.

As far as how to approach her thats all on you and what’s in the realm of your personality. You definitely want to establish the fact that you are interested in her and this is easily done by letting her know you are attracted to her. The dreaded friendzone usually results from a man not being assertive enough to let a woman know what he wants or a woman not being woman enough to let the guy know what she doesn’t want. Being overly assertive comes across as giving off the sleaze ball steez (what we call being ‘rapey’) so be sure to not come on too strong. Strength is in confidence and action, not in words and unfortunately thats not something that I can coach. You being a ‘Shy Guy’ suggests that this isn’t your strong suit but thats me being assumptive, and assuming you get her info the first few times you speak with her just be sure to drop subtle signs of more-than-friends interest on her. From a compliment here to an offer to hang out in an intimate setting there be sure to reinforce those initial talks with your interest in her but do so sparingly, nobody likes a ‘thirsty’ person. If you see it veering towards the friendzone after a few conversations then be direct before it goes into the deadzone where you are forced to watch her date lame dudes and give her advice or tell her she deserves better. Take it from me, that shit SUCKS!

But give it a shot, at worst you will learn something about yourself. Hope this helped. Hit me back and let me know if you got the girl. Good luck!

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