I want to ask this question in two different contexts. The first is you are romantically/sexually interested in your female best friend. The second is you are not interested in her like that but the friendship is very important to you and she means a lot to you. The reason for these two contexts is because one of the two is the real context of my friendship with my male best friend. There is no question that I mean a lot to him. He tells me often that I'm pretty much his favourite person. He loves me a heck of a lot - only thing I don't know is if there is a chance he could love me in a different way.
SO...
I've liked him as more than a friend for a long time. Our friendship is extremely important to me, as it is to him. There have consistently been barriers to me making any moves, but I'm feeling more and more like it is time to. I've decided that I have to, whether I get the answer I want or not. Now, I just need to figure out how to move forward.
Option 1 is that I simply talk to him about it. Tell him how I feel. Ask him if he feels the same, or can see himself starting to feel that way about me.
Option 2 is to start flirting with him - touching him, leaning in close to talk to him, complimenting him, etc.
What I'm not sure about is if he would be weirded out by my advances if I go with option 2. I'm not a particularly flirty creature, which is why I think he'd probably be confused by my behaviour and perhaps weirded out.
The thing is, I think in the long run I do need to just tell him, but I think that maybe the reason he hasn't thought of me like that before is because I am very much one of the guys and that makes it difficult to see me in a sexual or romantic way. I'd like to plant the seed for him to start seeing me that way by behaving more like a sexual/romantic prospect rather than just a friend. We have been friends for over two years, though, so for me to suddenly begin behaving very differently will probably seem odd.
I'm concerned that if I just talk to him about it without first establishing myself as a romantic/sexual prospect, the answer will be that he just doesn't see me that way.