You don't have to make it too complicated. Just come up with a good excuse to ask her out, like a movie or a concert, and casually mention it to her in conversation. Ask if she wants to go.
You can't force him. Pressuring or nagging (even just reminding him) will push him further away. You may have to just wait it out. But if you don't think he'll...
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...
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...
