Possibly, but trying a cold approach might trigger her defense mechanisms. Instead, try to start things off with a casual conversation so she feels like you aren't just angling for her number.
Well, asking out someone you don't know on the basis of her internet photos is by definition kind of creepy. You can try having a few solid conversations with her...
If your confidence isn't there, build it up first. Get to know him, let him see how cool you are, and remember that you're a catch. You could try pumping...
