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1. 'Do I need to ask his parents' permission first?'
If you really want to turn tradition on its head, then why not ask his mother for her approval? After all, with you taking the reins and proposing to him, it seems only right to ask the matriarch of the family what she thinks.
2. 'Do I need to buy him an engagement ring?'
It doesn't have to be a ring. It could be a pair of cufflinks, or a piece of art - anything that lasts a lifetime. A watch is another nice idea as you can have it engraved with your proposal date. It's something he will wear every day - just like an engagement ring.
See also: Marry by force!
3. 'Surely if he hasn't asked me yet, then he can't be ready to get married?'
There's a very easy way of working this out. Firstly, you need to know if marriage is even on his radar. Have you discussed getting hitched with him? Does he balk at the idea of a wedding and find every excuse to leave the house and visit the pub? If so, then marriage might not be quite right for him just now. However, if you have had 'the chat' and you know he is heading in that direction, it's a very positive sign.
4. 'Will I always be left wondering would he have asked?
'If you are only proposing because you are sick of waiting for him to do it, then it's the wrong reason to get down on one knee. When women contact me wanting to propose I always check they aren't just doing it because they have got tired of waiting. If, however, you are proposing for the right reasons (i.e. you want to be with him for the rest of your life) then you can pretty much answer this question yourself. If he says 'Yes' to your proposal, then it obviously means he sees his future as being married to you. Which means, if you hadn't asked, he probably would have done so anyway.
5. 'Will people think I'm desperate?'
Do you care? The opinions of your friends and family are the only ones that should matter and if they can see you're in a happy relationship and meant to be, who cares who's doing the proposal?