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What are your interests? If you could take a class or join some kind of club you have an opening to talk to women about your common interests. Having a good job, going to the gym and looking good are all great but they aren't exactly conversation starters. Once you're able to meet a woman and get to know her those things will supplement you.
How can they even tell if a guy is shy or not at first sight? They can't.
It's actually pretty easy.
The 'shy' guy is usually the quiet one, sitting and looking uncomfortable in social situations, perhaps stirring a drink or looking into the glass. Not really making extended eye contact, and even if he does smile for some reason it seems forced.
I'm pretty outgoing and I've dated shy guys before. They're endearing for a while, but after a few months of making excuses as to why your SO doesn't show up anywhere with you it gets a little tiring.
What is your dating life like? Is it non-existent? Do you have options but the females aren't up to your standards? Or are you casually dating but it never progresses because you realize there's no physical attraction?
None of us can tell one way or another. Three of the items (good looking guy, good job, good shape) are a matter of perception and his perception and other people's may be totally different. The other 3 are facts. Out of them only 1 is neutral. The house and the car may suck and be a turn-off to other people. For instance, if somebody has a "farting" (as I call it; modified in other words) car, a car with sound system that rearranges my guts even if it's just next to me at an intersection, a car that's peeling and falling apart, etc., not only does this not count towards "having" a car (which to me is a necessity not worth even mentioning in most places in this country), but it also puts in display some "wonderful" character traits and hints at living conditions I don't care for one bit.
I am nice, funny, caring, loving guy that just needs to overcome the shy part. I am into my personal health appearance and like to stay in shape that is way I stay away from the bar/club scene since most of those places require you to drink.
You need to put your self out there. My first reaction was to tell you to go to a bar after work one Friday and relax. Most shy people have insecurities of some kind that stop them from feeling confident in a new situation.
So as that's the case do something you like doing like circuits at your gym, running club or a book club...maybe? (sorry grasping at straws with your listed interests). Hopefully if it's something you enjoy you will relax and feel less shy and a little more confident. Plus you will hopefully get chatting to someone with the SAME interests as you.
Don't be shy. You have a lot going for you, no reason to be shy. Remind yourself: "Look at my "loser" friends, they have girls, s**t, no reason I can't."
Socialize some. It is great that you're a "funny, caring guy", but how's any girl going to know that if you don't get to know them?
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