Best friends? Maybe not.

So, I just got off the phone with my best friend. I've known him since about 12 years now. Right from school to now we've kept in touch. We were pretty close. Quite the opposite in disposition. I would get home from school everyday and tell him all about what happened in school. And he would just sit there listening. Never talking. Considering I am usually quiet one, you can imagine how quiet he must be. Hmm...So maybe we are not quite different after all.

So yeah we grew up. Made friends. Had crushes. I would tell him all about them. Tell him how it breaks my heart to see them in love with someone else. I remember even crying over the phone once for some other guy and he would just console me. He told me about his girl and how she lied to him.

All this while never did we have feelings for each other. I mean I cannot think of him as "my guy".

Today he calls me and says I've been thinking from sometime now, and I think I see you more than just a best friend. I was like :O!
Then he goes on to tell me about sometime where he had introduced me to one of his friends and I spoke to him more than I did with him. He was uncomfortable then, but brushed off his feelings thinking they were just best-friendish feelings. When he thought back about it recently, he thinks he was Jealous.

We recently went on a trip together. Friends and family included. I thought I saw a look in his eyes- an irritated sort of expression when I wasn't spending as much time with him. I sorta brushed it aside.
Didn't realize what was about to come.

Now it's all so weird- I mean I don't feel anything for him. Like nothing! But then thinking about how our families our close and him knowing everything about me..it probably would seem wise to say yes to him.
But then again I don't love him...I feel bad that I will be breaking his heart, coz I know exactly what it feels like when someone breaks your heart.
Strange is love.

I told him maybe he thinks this is love because he has opened up to me. Maybe he just needs to talk to other people more. (Didn't know what else to tell him)
Then he says take your time and think about it.....But I am pretty sure about what I feel for him...
How do I tell him that without breaking his heart?
Feeling weird/bad that I lost my bestie. Things will never be the same again now.
Why oh why do relationships have to be so complicated?!
Why oh why can't a girl and a guy be best friends!!!!

It is complicated!

See how people have their status messages as "It is complicated". And then you wonder, how can it be "complicated" you're either in or out of a relationship. This is one such example of complications!

This is a complex love story about P. He was the first guy she loved. He made her believe he liked her too. They were together for a while and then one day the guy decides to move on saying this is not going anywhere, let's look around and find other people.
Should have been the end of the story. But this was just Blow #1.
She tried hard to forget him, but every time she met new people she would compare and think he was so much better. And as time passed by, she began "hating" P. Hating in quotations because every time she even got a glimpse of him, she would go weak in her knees and withdraw away from him, fearing he would hurt her again.

Meanwhile he gets "committed" to another girl. And when she had opened up to him after he had assured her he will be there for her always, leaves her. Reason? The Jane was too plain for him. A few flings later P and his first girl get back together. Happily ever after? Not the case.
Both of them profess their love and he convinced her once again, that she was the only one he loved. She wasn't convinced at all, but as time passed by she gave in.
Was she stupid or what?! Or the guy was a real smooth talker. Whatever it was, they were happy for a while and then followed the usual problems.
Jealousy. Insecurity.
But on the positive side, no signs of infidelity from the guy considering his history.
They made compromises. They had fights.
Both of them had shortcomings.
And then he leaves her again. Blow #2.
And the cycle repeats.
Neither of them is over the other but they are not together.
Hence, the status " It is complicated".

Questions I have for you :  I probably have to get married soon. I don't want to be in P's situation where he leaves her and goes as per his convenience. I'm married and I realize some qualities in him are not to my taste and vice-versa. Both of us compromise. And that is how it is meant to be.
Considering you are happy with someone, and you have a few fights and make up, repeating in an infinite cycle, what is the condition to check to get out of the loop? How does one person decide "The End"?