Yupa wrote:
Any tips? I've never been the one to initiate this kind of thing (that's usually the other person's doing), so I welcome any good advice.
You don't. If your perspective on relationships is that you have to negotiate with the other person to get them to do something romantic with you, then I don't think that is a very healthy perspective.
If a person choses to make out with you, it should be entirely of their own free will, without any persuasion on your part. That's not to say you shouldn't ever try to initiate anything, but there is a difference between initiating and persuading.
As for when you should initiate this, I couldn't really tell you. However if you have any doubt, it's advisable that you ask or verbally indicate your feelings.