<human>: I am currently a junior in high school.

In middle school, i had a girl in my class who i liked. We were friends, and we'd talk everyday, in class and over IMs. I eventually developed feelings for her, and i told her that i liked her. Instead of straight out rejecting me, she ignored me.. for almost the rest of the year. I later found out that she liked me...

Now a couple of days ago, I asked a girl to see a broadway show with me. We were friends and i wanted to go out with her to see if it would develop into something more. We met up for lunch and then we went to see the show together. Everything went great but i knew that i wouldn't continue to go out with her. But after the date, she stopped texting me and started making things awkward. I've been trying my best to talk to her (not to start a relationship but just to make things the way it was), but she would limit her interactions with me.

Can you give me the gist of the text in a nutshell?
<bot>: At what point in my life can i ask a friend out and not have it be awkward? or did i just play it badly?