Always Been Single

by Dante
(Illinois)

I am an 18 year old guy and I have always been single my whole life. The closest I have ever been to having a girlfriend was a girl last year who said that she would go out with me if I wanted. I didnt know her that well, but I thought she was attractive, and I was certainly considering going out with her, just to give the dating scene a shot.

That was, until I found out that she only wanted to have me around to make her current boyfriend jealous.

Before that, there was a girl who was really good friends with me, and I had a very serious crush on her for two years. She seemed to be showing me a lot of signs of attraction, and I was almost entirely sure that she liked me, but just two days before I planned to ask her to our Homecoming dance, I found out that she had a boyfriend, and to make things worse, I saw them kiss for the first time on my birthday.

I had to spend about a year trying to get over it. Now there is another girl that I am starting to have feelings for. However, I am still apprehensive of the whole dating scene due to my previous bad experiences. This, coupled with my already prominent shyness around this girl, makes it very difficult to try to advance our current relationship in any way. I find it difficult to even speak to her in person due to being so shy, and usually I only manage to say a few words to her each day, if at all.

She talks to me almost every day and is always smiling and telling me how nice she thinks I am. I always try to sneak glances at her during class, but she has caught me a few times. The latest time, I quickly looked away, but in the corner of my eye I could see her continue to look at me for several more seconds with a smile. Recently, I found out that she has another admirer, who left her a note in her locker saying that he thinks shes attractive and would like to get to know her. She didnt seem to think too much of it, even saying that it was slightly creepy, but she did say that she wants to meet the guy.

My question is actually four-fold:
1. How do I get over these past bad experiences?
2. How do I overcome my shyness around this girl?
3. How can I build upon our current friendship while at the same time advancing it towards a romantic relationship?
4. What should I do concerning this other secret admirer? Is it even something that I should worry about?