Hi there @stardust :) listen to your instincts. If you feel that maybe its not the right time, then just wait a little longer. Things can get complicated when you open up. I was head over heels over a very close male friend of mine! When i opened up, things got a lot more complicated. He told me he didn’t want to ruin the friendship we had. Super hurt and jealous of his female friends as the days passed. I couldnt be around him anymore. So be careful…you might get really hurt. Observe a little longer..and perhaps put a little bit of distance between you. See how he reacts.

It is the best way for something to happen.

It’s what I hope for myself.

The other way, infatuation to romance to… well, let’s just say it hasn’t been working for me.

I was the best thing that ever happened to me, we were friends first and when it all changed it was awesome because we knew each other so well.

I hope it works out for you

Yes, I have.

What you have to weigh is the possibility of losing the friendship. At the very least, things will probably never be the same.

There are ways of approching the subject that make it more of a wondering or pondering type of question rather putting it all out there. You could ask him if he has ever wondered what it would be like to date each other…. You can always say you have been pondering it because someone happened to bring it up. I am sure others have asked and its only normal to just wonder.

Theis is where subtle flirtation works well. If you are a good flirt, you cast the line and see if he is at all interested. If you are intuitive enough, his reaction will tell you weather you should persue it. If he is not interested he will either get a look of horror in his eyes or not respond. If he IS interested he might throw a test flirt back or just move in closer to try to figure out if what he thinks he just saw was real.
Courting and ego preservation is a delicate dance. In recent years the “just tell him and don’t play games” camp has prevailed.
I think a lot of friendships have been destroyed and feelings have been hurt because people abandoned the fine and subtle art of courting.

That’s how I ended up with my current boyfriend! I told him how I felt and we’ve been together ever since (5 years).

wow guys; im jealous :p

Me personally, would start flirting and through those suddle comments out there and see what comes back, if you get the green light than tell him how you feel. The best relationships start with a great friendship. I think you should always be honest with how you feel, and even if he dosen’t feel the same for you, as long as you can accept it so should he.

If you ask, and he isn’t interested, then that will be very awkward. It might ruin the friendship. If it’s there, let it happen organically. You can flirt a bit. If he responds, then take it away. If not, let it go.

Take it step by step…every green signal he gives you, escalate it.

How could those feeling happen prior to a friendship?

Yep…..
It sounds like you are level headed and one to ensure your actions. This is good.

You get to a point where the fear of loosing it by not saying anything overcomes the fear of it not being reciprocated.

That’s when you know what to do.

It’s happened to me once or twice. Both times I think it was out of loneliness and needing romance that I started to want more than friendship. I would start thinking and daydeaming about the person and what it would be like if we were more than friends. I was young though and these were not serious infactuations although I convinced myself at the time that they were. I was in love with love and to me a daydream was better than nothing. Obviously now that I am older and wiser I see those situations more clearly. In your case I am sure the feelings are based on much more than mine were. I guess I would ask myself some serious questios. First, what am I hoping will come of this? I would guess since it’s a friendship you would never risk threatening that by a short term fling. That would probably be painful for one or both of you. That leaves question number 2-would we be compatible as more than friends? This may seem overly cold and analytical but just because you get along great as friends doesn’t necessarily mean it would work on other levels. I’m not even talking here about sexual chemistry. I mean, would you think you’d be happy living together? Would things you find funny and endearing about him become annoying if you were a couple? Like Blueizh says there comes a point when you feel like you will explode if you cannot let him in on your feelings. Then you will have to take the chance. Maybe if the answers to the other questios are all good you may do it sooner rather than later

Thanks for the responses guys :) I’m opting for measured thought on this as I don’t want to ruin the friendship. @Earthgirl Thanks for that – those are some helpful questions.