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I wouldn't snap a few pics at work....that sounds horrible. Spend over $40 on a nice haircut, hire a professional photographer and take a few different looks in your nicest clothes. You'll attract a much higher caliber girl. The problem is when she meets you, you have to maintain your appearance.
Stop wearing hoodies and beanies if you want to attract a hot stylish girl. Up your style game and many more girls will be attracted.
Yeah, that's the thing I'm worried about. If I overdo my look online, it becomes a hassle to keep that up. Like I said above, I'm not sure what I can do with my hair, it's thinning on the crown, and temples have receded. I keep it under an inch, and maybe go with a little messy spike/bed head look if I'm going out. You know, being confident in what you have and not trying to hide it.
And to be honest, I'm not into the super stylish girls. I like the country, rocker, or nerdy types. Not saying I would turn down a fun night in bed with one, but I feel it's easier for me to be natural around the types I listed. If I can be natural, I'm much smoother and have a better success rate.
And glasses or no glasses, I love my beard, but I wonder if that's a bad thing. I barely look old enough to drink without it.