I think Valentine's Day is one of those holidays that was invented for the sole purpose of making single people feel shitty. It is similar to most other holidays in that it has an elitist facet: couplehood. Only couplehood is one facet about which most people have little choice. That and, many people who choose to celebrate it have partners who don't.
Nevertheless, like New Year's, I've had quite a bit of luck on past Valentine's Days. Last year, for Valentine's Day, I went to Ashland with my then-sweetie and spent 3 nights in a B & B. One night, after we had our first and only fight, he gave me a beautiful necklace. I gave him a lame tie and a tie bar and we broke up two weeks later.
In 2004, I went to Las Vegas with ex #6 for 36 hours, got stupendously hammered, flew back, and slept for the entire next day.
In 2003, ex #4 and I were starting to patch our relationship up when he was deployed to the Middle East. That was a sucky, sucky Valentine's Day if there ever was one.
In 1996, being the cash-poor college student I was, I spent a good amount of the day on February 13th making a batch of disgustingly rich brownies as my gift for ex #1, then went by his house the next day to surprise him. It was then I found out that not only did we not have V-Day plans, but he was playing hide-the-testicles or some other testosterone infused sporting event with his friends. I was a crazy teenager, so I called him, oh, 10, maybe 12 times that day; each call went unanswered. Until, at 11 p.m., just as I'd finished crying myself to sleep, I hear a knock on my bedroom window. He handed me a note with an amazingly sweet apology. Retrospectively, he should have gotten dumped like wiseguy into the East River, but I forgave him, and we continued to torture each other for another year.
The best Valentine's Day ever was in 1999. I had just started dating a guy a couple of weeks earlier that I'd met at a concert I was at with ex #1 (see above) and ex #2. I didn't yet know that he was an asshole, but I would find out eventually. Anyway, he was from Kansas City so he knew where all the really great haunts were. He got us reservations at an incredible restaurant and then...don't pass out when I say this...we went ice skating. It was the most romantic date of my entire life. At one point, we got separated out on the rink. A few minutes later, I looked over and saw him teaching some little hussy how to skate! I snickered, decided that two can play that game, and gathered up my nerve. I clumsily skated over to two cute guys that were leaning up against the opposite side of the rink. I explained to them that I was needing to make my boyfriend jealous because his attention had been divided so if they would please smile and laugh at whatever I said that would be really great. They played along, but probably because I was smiling and blushing. Before I even finished my sentence, ex #3 was at my side and swept me away across the ice. I smiled and winked at the guys and went on about my date. I loved that we could play little sweet jokes like that on each other. But I think if there had been any hard feelings, they would have been erased by what I did to him in the car on the way home.