When I was in tenth grade, I started “going with” a boy who lived about 2-3 miles from my house. Mostly, we just talked on the phone, but sometimes my parents would drop me off at his house for dinner or game night (Monopoly, Sorry, Scrabble, etc.). Sometimes, his parents would bring him to my house for dinner or to watch a movie. It was very sweet, and he and his family were wonderful people.
Valentine's Day fell on a Saturday, and he wanted to bring my gift to me then, but his parents had plans for that day, and so they told him we would not be able to see each other, so he would have to wait until Monday to give me my gift. He was too excited about the gift, so he decided he would bring it to me by bicycle.
I know this doesn't sound terribly romantic yet, but imagine my surprise when the gift turned out to be a four foot tall teddy bear.
My mother called me over to look out the window, and there was my boyfriend, peddling up my sand/gravel/seashell driveway with a giant bear tied to his back. In his hand was a bouquet of carnations- red, pink, and white.
He came into the house, and he presented me with my gifts. I can't remember at all what I had gotten him. We visited for a little bit, and then my parents offered to drive him home. He declined politely, and then he rode off.
Later, as I was looking at the bear, I noticed that it had been sewn in patches all over. It looked like it had been stabbed. I was telling a mutual friend of ours about this, and he said that Brian's best friend had stabbed the bear twenty times because he was angry that Brian was paying so much attention to me. He was furious with the friend and stopped hanging out with him completely. Brian then asked his mother to teach him how to sew in order to fix the bear in time for Valentine's Day.
The gift, the gesture of riding with it on a very public street to get it to me, and repairing it when some jealous jerk had effectively destroyed it made the entire experience the most romantic high school memory I have.