I don’t have a particularly good Valentine’s Day track record. Mostly because I was single – and not the mature and the contented kind of single – for most of my teen years, but also because of charming fellows like the ex who cut it short (as in, dropped by my place for approximately twenty minutes) by claiming to be busy with schoolwork, then later admitted that he’d actually been free but just didn’t feel like spending time with me.

With gems like that it’s kind of hard to choose just one horror story, but I think this one took the cake. This ex and I had only been dating for about two months, and he told me at the beginning of February that, tragically, he had already made a pact to spend Valentine’s day with a platonic friend well before we had begun dating. I wasn’t quite sure how to take this, as my dating history at that time had been brief and far from ordinary. Was this normal male behavior? Is two months too short of a time to reasonably expect to spend Valentine’s day with someone? Would I look totally insane if I were to wrestle him to the ground and demand he cancel on her? Ignoring the warning signs, I decided to just roll with it.

I went ahead and made my own plans; a male friend and I bought tickets to a club downtown and I planned to spend the night out dancing and drinking away my looming Valentine’s day doubt and awkwardness. When my ex asked how I’d be entertaining myself, I told him, and I suppose he started to feel threatened (the male friend in question was gay but I somehow I forgot to mention that to him – oops!). He offered to cancel his plans and spend the night with me instead, but I told him that it was a little too late. I wasn’t going to bail on my friend after we’d already bought the tickets.

A few days before V-day, we went through the drive-thru at a local coffee shop where his date worked, and she happened to be at the window. I sat in the passenger seat like so much chopped liver while they discussed their upcoming night out. She asked him if he was excited, to which he replied, like a gentleman, “Hell yeah, I’m going to get you wasted and feel you up in my car!” Oh, how they laughed!

Then we drove away. I immediately went from being reasonably well-adjusted to the whole setup to being furious at him for being so disrespectful. He told me he was only joking, but I thought it was in pretty bad taste. Being, at that time, a young woman who was both environmentally conscious and lacking in self-respect, I cleverly managed to repurpose my fury as insecurity and self-loathing, and continued dating him as if nothing had happened. But at this point, I didn’t really give a crap whether or not we spent Valentine’s day together at all.

The day finally came, and he asked me to stop by his place that afternoon just to say hello. I obliged. When I walked in the door, I was greeted with “I hope you weren’t expecting a present because I didn’t get you anything.” Given his track record and my own blossoming intuition, I hadn’t expected anything, and so I wasn’t terribly disappointed. Then he hit me with some more news: he said his date had told him that she’d had a medical emergency the night before and had been hospitalized, so she wasn’t exactly up to sampling the theoretical delights of his backseat anymore. I asked him if he wanted to come dancing with my friend and me, but he declined. I went anyway and ended up having a fantastic night out; I checked my purse (and phone) at the door and had amassed about 6 texts from him by the time I’d left, asking how I was and what I was up to. I found out he’d spent the night as a third wheel, hanging out with his friend and his friend’s girlfriend. I felt sorry for my ex’s would-be date, but couldn’t help thinking that the end result – an awkward and uneasy night for him – was just desserts. And because I had the self-esteem of a shoe, we still ended up dating for over a year after that. Go figure.