Okay, so I really like this girl. We've been friends for about 2 years. I think she's smart, beautiful, and cool. I know that it would basically be bad if I just chatted with her on Skype and asked her out, but would it be inconsiderate if I were to video chat with her and ask her out?

Not that I have any experience in the field, but if you're going to ask someone out, it's best to do it in person every time, unless you're already going out with them.

 

At least that's my opinion.

Well my girlfriend revealed that she liked me through a tumblr message.

And it worked out pretty fine?

It depends on the girl though.

Do it in person. If there's no way you can do that because you can't see her, then video chat, and if you can't do that, then message her, but before you message her, call her, if you can't do that, then you message her.

Video chat would be a lot better than a PM or IM. But make sure she's in a 'good' mood first.

always better to say it in person, but i guess o__0

If you're casual about it... invite for just a normal friendly hang out and once you're actually hanging out say somethin' like 'We should do this more often. Like... as a couple.'

I agree with ssceles. If it's going to be an official date then in person is always best, but setting up a comfortable atmosphere can be helpful and fun.