Having been through the exact same situation as you 2 times, and having spoken to them, I can only say that both of them were a disaster. It's really unlikely to escape the friendzone, it has happened sometimes to people I know (well, only one person actually) but I wouldn't get my hopes up, be prepared for the worst. We're still friends with both of them, but I wish we weren't, because every time I see them I feel like shit. But... they call me and I don't want to sound like an asshole, neither do I want to give them the satisfaction of telling them that "Look, I don't want to be friends anymore because it's too hard for me".
In my opinion, what would improve your chances (slightly) is to be casual and confident about it, don't be dramatic and don't use scary words (I saw you mention "love" in your post, do not use that word). Then again, I did it in the best way I could think of, in a nice environment, on a night out alone, when we were both in a good mood, with a slight smile on my face, told them that I liked them in a non-friendly way and believed that we fit, asked them what they thought, and yeah...well, they didn't. Could be because I'm fucking ugly though. That always fucks things up. Sadly, it's easier to wade through a number of drunken unknown chicks at bars in case you find something worthy than go after one person that you know and trully appreciate.
By all means do it though. In the end, it's better to feel like shit because something didn't work than to feel like shit because something might have worked but you didn't have the courage to make sure.
In my opinion, what would improve your chances (slightly) is to be casual and confident about it, don't be dramatic and don't use scary words (I saw you mention "love" in your post, do not use that word). Then again, I did it in the best way I could think of, in a nice environment, on a night out alone, when we were both in a good mood, with a slight smile on my face, told them that I liked them in a non-friendly way and believed that we fit, asked them what they thought, and yeah...well, they didn't. Could be because I'm fucking ugly though. That always fucks things up. Sadly, it's easier to wade through a number of drunken unknown chicks at bars in case you find something worthy than go after one person that you know and trully appreciate.
By all means do it though. In the end, it's better to feel like shit because something didn't work than to feel like shit because something might have worked but you didn't have the courage to make sure.