Believe it or not, only one of my relationships have resulted from straight out asking a girl out and that was my first girlfriend from way back in 6th grade.
That relationship didn't last very long, however. Only being in 6th grade and this being the first serious relationship for both of us, we were
incredibly shy. I don't believe we even held hands until after a week or so, so that should show just how shy we were at first. Now, we did eventually start kissing in private, but her friends would constantly pressure us to kiss in front of them or "it wasn't real". At this point, I would've been fine with it, but she still wasn't comfortable with kissing in front of people, so we didn't, but they continued to pressure her about it until she finally couldn't take it anymore and decided that she wanted to break it off.
Besides that, most of my relationships were either a more friends with benefits sorta deal or they just kinda
happened, not making it "official" until after we're basically already a couple.
My most recent relationship was actually a long-distance-relationship that lasted for almost three years:
We actually met online and became really good friends over time, to the point where I eventually decided to visit her. We had a good time being together and we became even better friends after that until, before long, she asked me to visit her again and I agreed.
Again, we had a great time together, but she asked to come to my hotel room the last night and that's when she told me that she'd be interested in being in a relationship with me. We talked it over for hours, about how difficult it would be and all that, but we eventually agreed to be a couple. Nothing really happened that night besides a couple kisses and a lot of cuddling, but I ended up extending my stay by another day and took her out on a proper date the following day before having to leave that night.
Now, our relationship got better and better as time went on and we were visiting one another every 4-6 months, which isn't bad for a couple of high school students traveling about 1,009 miles! This continued for almost two years and we became increasingly more intimate with every visit, to the point where a couple visits consisted of nothing but sex and cuddling, but then she graduated (she was two years ahead of me in high school, because I failed a grade back in elementary school after switching back to public school and because of a late start from my birthday being in October).
She had a part-time job at the time, but all of the money she made pretty much went straight towards her tuition and the couple bills she had. I was struggling to find a job myself at this time and, because of that, our visits started getting more and more scarce. After almost a full year of not being able to see each other and having no idea when we'll be able to next visit, we both started to feel it and we eventually decided to go our separate ways.
We still talk occasionally and we try to remain good friends though!
I'm single at the moment and besides a fling here or there, I plan on staying that way for a while.