1999: I had braces installed between fourth and fifth grade. This may seem like an odd statement, but they gave me confidence. I’d had some chompers jutting out in wild trajectories prior to obtaining them, and the braces really helped straighten things out quick. I’m convinced this new-found bravado helped me show off at Sunday School (you know, the place to woo girls), which in turn helped me convince the love of my life from ages 6-11 to become my “girlfriend.” This is the first year I celebrated Valentine’s Day on a higher level than stuffing X-Men cards into huge envelopes at every person’s desk in a grade school classroom. I gifted flowers to Kristin the Sunday before V-Day, and she gave me a gigantic Hershey’s Kiss.
Kristin and I had a tumultuous split a couple of months later. She is now happily married with a beautiful child. I went to her wedding. It was held at the same church where we used to go to Sunday School.
2000: I gave Brittnee — the first girl I ever kissed on the mouth — a cheap ass necklace with a heart pendant from K-Mart, I think, and also a Train CD. (She dug “Meet Virginia.”) She gave me a leopard Beanie Baby, which I still have at my parents’ house in a special memory drawer, despite it being one of the oddest gifts I’ve ever received.
She is engaged and pregnant with her first child.
2007: I spent a platonic Valentine’s Day with my friend Em, since we were both single. I think we went to a movie, but the thing I remember most vividly is that we belted out some Celine Dion in her car.
She got engaged Christmas Eve.
2008: Valentine’s Day occurred in the midst of my most serious and long lasting relationship to date. I was flush with cash from a sports stringer job I had at a newspaper in my college town, and so I took my girlfriend Rachel out to a dinner at a restaurant my friend had suggested. He said it was extremely expensive. I didn’t care; I was going to make it rain. At the time, I was disgustingly head-over-heels for this girl, and I wanted to show it in any way I could. So, instead of saving this disposable income for something normal college kids spend money on, like spring break, I opted instead to blow a sizable chunk on this meal. And another, more sizable chunk on a gold ring with a small diamond in it that I gave to her on that night, because I am original and unique.
She’s not engaged now, but she’s been with the same guy since we broke up, a few months after our Valentine’s date. They are two of my closest friends in the world.
2009: I came home from college for the weekend and ended a months-long repose from the dating world. I re-released myself into the wild by going on a first date to a movie with a girl named Juli who I’d been talking to for some time. It was awkward, but she gave me a kiss at the end of the night, probably because she felt it was obligatory. We talked less and less after that night, until we didn’t talk at all.
A few months later, Facebook told me she was in a relationship. A few months after that, she was engaged. Her wedding is this summer, according to my online research.
After this date, I went home, opened my laptop and sold the ring from the previous year to Cash4Gold.com. I didn’t get anywhere near what I spent on it, but it did help me pay for my next month’s spring break trip to Florida, where I jokingly got engaged to a girl by presenting her with a RingPop.
That girl is also engaged. This is unrelated, but seems somehow pertinent.
2010: I went home for the weekend, because I had somehow snagged two tickets to a Ben Folds concert in Pittsburgh. I took Taylor, the girl I’d been dating long term, to the concert with me. Folds played “The Luckiest,” one of the greatest love songs of all time, and then later that night I told her I loved her. It was the first time in years I’d said it to a woman who wasn’t my Mom.
Not long after that, we went our separate ways. I think I broke her heart, and I felt terribly about it. At least, I did until she let me know she’d gotten engaged this past Christmas Eve.