Tell Me If It's Chilly Outside

Most everyone I know is in a relationship. New, old, whatever. It leads me to believe I’ve missed out on something along the way. And when I do think about what I could have possibly missed out on. She comes to mind.
 
Had drinks yesterday with a friend from home. Told him about everything. There are certain areas in my life that I keep private until two important requirements are met. First, I have to consider this person a good enough friend and second, they need to ask me about it.
 
Now, last night he never asked. I didn’t plan on telling. Nonetheless, I told him. He wants me to contact her. Why does this feel like a bad idea? I’ve thought about contacting her for years. Its been a balancing act to keep myself from doing it.
 
Now I don’t know what to think.