Spike your hair and maybe contacts Plus just smile normally and dont try to do a pretend smile. =D all else is fine.

you need a fashion overhaul. the fact that nobody has truly told you that scares me.

Personally i would start beefing up abit and wearing more fitted clothing. Maybe try a blazer ?

Yep better fitting shirt and jeans, take their advice. Will make a huge difference and is absolutely essential.

You need to find a female friend, someone with good sense of fashion, get them to come out with you and help you choose (hell it coudl even be a 2nd day idea )

As a last resort try and rely on the salesperson's advice, see if you can find someone very friendly and helpful and not trying to just push something on you - go around and try things and don't be afraid to tell them you're just getting ideas and you might come back. That way you can go back to the one you think was most helpful.

Get a haircut

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Buck on ! ! !

don't even think of polishing your nails black... bad bad idea. There are some styles (like goth/emo) that can go with the nails, but definitely not yours. Not to mention that nail polish + man should not go together anyway.