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OOT relationship experts-- advice needed. TL/DR

Cliff notes at the bottom;

I'm a regular poster (albeit not in OOT), but am using the gimmick because there's only 2 other people that really know the full story that relates to why I can't pick up girls today. It's not that this story is particularly revealing/exciting, I just don't tell it to a lot of people; rather, the story is quite mundane and uneventful.

Some background on me necessary to consider.

-- I'm actually a fairly sentimental guy. DEFINITELY a romantic. This is something that a lot of people don't know about me, and probably why when I am in a relationship, I tend to have very strong feelings. Moreover, I have tried random hookups in the past and it's not for me. I'm a relationship kind of guy.

-- I love music. I play 3 instruments well, and when I'm bored, I usually compose. It's not always good, so I throw away the crap and write down the good stuff. When I have played songs for friends/acquiantances, I have been met with very good reviews in spite of my mediocre singing ability.

-- I'm a senior in high school, and will be going away to university next year with a number of my close friends. I'm absolutely hoping that college is a fresh start for me in terms of relationships.

-- I have no idea why I feel the way I do about the girl that I will refer to as Kristen for the rest of this thread.

-- Physically, my female friends have told me I'm a good looking guy. I don't know how to rate my face, but I can't imagine that it's too atrocious. As far as my body goes, I'm a muscular 5'8/170 and lift often.

-- I'm neither introverted nor extroverted. I guess I'm slightly more happy being in a group, but am also perfectly fine just sitting down and writing music.

-- I have a good sense of humor and can get laughs easily, but my personality is nothing special.

"Kristen"

We met on vacation, 3 years ago. Yes, I was 16. Yes, I know you're thinking there's no way in hell you can develop significant feelings for someone in such a short period of time, esp when you're that young. Well, I did.

There was an instant connection from the first time I saw her. I was walking on the beach, and saw her. I wanted to go talk to her, but for some reason didn't. Fortunately, she did that for me and came up and introduced herself. She was on vacation with her best friend, and the three of us talked for hours that first night.

At this point in my life, I had not been in a relationship before. It was more because I simply hadn't found a girl that I had wanted to be with rather than I hadn't had the opportunity. But she was different.

After talking to her for no more than 5 minutes, I could just tell. The next day was oddly similar to the first night-- the three of us just chilled and talked a lot. There was never a dull moment in the conversation, and I couldn't believe how fast I was falling for her.

Her best friend told me the next day that she felt the same way. This still might be the single happiest moment of my life. Obviously, I suspected it, but my girl-reading skills were even worse back then than they are now.

We spent almost every moment of the next 4 days together. I think the best friend realized what was going on, and really just let us go by ourselves. A lot of the time, we would just walk around, laughed at stupid stuff, and just enjoy being together. Somehow I felt like I had known her for years, when in reality it had only been a few days. It was perfect.

We kissed a bunch, and went a little further. I was fully aware that she would have had sex with me had I wanted to-- but I didn't want to. I knew it would hurt her later on, and knowing that I would have caused her pain just killed me on the inside (this is very important later).

The more time we spent together, the happier I was. I loved everything about her. Hell, I still remember every stupid thing we laughed about, the sound of her voice, etc. There are no words that I can type that would describe how I felt at this time, because it was far and away the happiest I've ever been.

And of course, at the end of the week, we had to split ways. We decided we would try to stay together (she lived ~600 miles away).

At first, it was great. We emailed several times a day, I called her all the time, and I was pretty sure I was falling in love. But after about 2 months, the pain of separation really started to set in. I still loved her, but realized that our relationship was proably causing her an unbearable amount of pain-- and the thought of this absolutely killed me. No matter how many times she told me she loved me, I knew that she was suffering because of our relationship; because of me.

So I finally looked at it realistically. There was no way I'd see her for probably 3+ years, so I obviously assumed we'd never make it that long. Given this, I decided that it would be less painful for her to break it off sooner than later. So I did. I never told her I still loved her, or that I was really doing it to try to save her some suffering. All I said was that I couldn't be the boyfriend that she needed and deserved when I was living in another city, and that we couldn't be together because of it.

Obviously, it took me a long time to move on. For about a year, I didn't want to date anyone else because I simply wasn't ready. After a time, I was sort of healed. I liked other girls, but never for an extended period of time, and in my mind... none of them compared to Kristen.

I've dated 4 girls since. I've never really been actively seeking a relationship, but if the opportunity presented itself, I took it. 2 of these were very short-lived, and two of them were ok. But I never felt the same way about any of these other girls as I did about Kristen.

Through all this, Kristen and I sort of became best friends. We still talk online for hours, and tell each other anything and everything. We never really discussed whether or not we might get back together in the future. This is still a huge problem for me. Throughout the last 3 years, I've never really felt that our connection went away-- our personalities are simply perfect together. I always kinda assumed that when I did see her again, we'd have a second chance. Yet, I've never really had a serious discussion with her about this. This hope for the future is something I still hold on to.

As you might imagine, I eventually got over her. Within the last six months, I'd say I've finally become ready to have a serious relationship with someone else.... and so I've been on the market. After many misreads and a few bad first dates, I'm still single. I think I'm going to stay this way until college (I'll be starting in 3 months), and would not like to go through the LD thing again.

So to the relationship experts of OOT-- I have a few questions to pose to you.

1) What's my future line with Kristen? I'll be seeing her for the first time in 3+ years this summer (my brother is now working in her city and I'll be visiting). Would this be a good time to talk about us having a second chance somewhere down the line? This is not a subject I'm comfortable talking to her about online/on the phone.

2) When we do eventually talk about the future, do I tell her why I broke up with her the first time?

3) I've written a number of songs about her/us. All of my friends have unanimously agreeed these are my best songs (although most do not know the story behind them)-- probably because of my feelings for her in the past. Do I play these for her/ tell her the story behind them?

4) For the most part, I intend to use this summer to figure out how to attract girls more often. Like I said, I don't want a relationship right now, but that doesn't mean I won't be hanging out with lots of girls.

5) Hopefully my experience from this summer carries over into college. When college starts, I'll be single and not wanting to stay that way. I'm guessing that worrying about Kristen at this time would be a terrible idea, and that I need to focus on girls at my school (my college has a ~60/40 female to male ratio for the record)?

Cliff notes; OP is a 19 year old romantic who fell in love 3 years ago and never really got over that girl. He held on to the hope that he could get back together with her at some point (she lives in a different city), and they have become best friends. With college on the horizon, he feels ready to find someone else and is for the first time actually seeking a relationship. When college arrives, should he worry about the ex-gf/current best friend, or chase tail at his school?

Thanks OOT.