Tradition 2: My friend fancies you

For: The playground approach is too useful to leave to pre-teens. Using a go-between preserves your dignity in case of rejection.

Against: If he thinks you've sent your friend to do your dirty work, he may question your character and it could backfire. Especially if he ends up getting off with your friend.

Verdict: Done with a deft hand and a friend you trust, this is a great way to find out if he's interested.