The problem with going to movies on first dates is you run a risk of seeing something terrible. Especially if that first date is in September, a time generally known as a movie wasteland.

So, that is how eight years ago I went on a date and ended up seeing a movie about a guy who is a cheater. Yeah, that kind of cheater. Not the “oh let me copy your math homework” variety. The “I boink other girls” variety. So yeah…It was a little awkward.

I don’t know if it is because I was so concerned with the date going well or because the movie legitimately wasn’t up my alley, but I left the theater with a less than stellar opinion of the 2006 movie “The Last Kiss”.  To me, the movie seemed relatively pointless. Why would I want to watch Zach Braff cheat on his lovely girlfriend (played by Jacinda Barrett of Real World London fame) to go run around with a child in college played by Rachel Bilson? What was the point of this? Was I supposed to sympathize with this greedy dude taking advantage of young impressionable girls?

At the time, I was about to turn 23. My date was a couple of years older, and, at the time, I was still too young and naïve to realize he was just one of many guys I was going to encounter in the next eight years who was scared to death of settling into anything.

You can credit growing old, I suppose. Working around the notoriously unsettled poker community probably deserves some credit too.  Either way, what I didn’t know then is a lesson I have learned in spades now: The Zach Braff character isn’t a horrible person—he’s just a guy nearing 30 who is absolutely petrified that he may commit to something that isn’t what he wants.

Upon rewatching this movie on a whim a couple of weeks ago, I suddenly felt like I was being educated, not irritated. To hear Braff’s character talk to his friends about why he can’t commit to marrying his girlfriend even though he is having a baby with her didn’t seem as whiny as it did that first time around.  I mean, as a female who doesn’t have commitment issues, I am on the girlfriend’s side here, but I also began to comprehend just why this situation that seems so unassuming to me can be so frightening to guys. The scenes in which Braff and his collection of male friends interacted felt like a glimpse inside the minds of the dudes who had baffled me the past eight years. Oh, I thought. Finally someone is articulating what these guys could never quite say.

But, much like Sex and the City, I wonder how much I misunderstood the movie as opposed to how much I have changed over the years. The way I viewed the “other woman” character makes me think this movie isn’t necessarily aging well, it is more that my age is giving me a better perspective to appreciate it.  Originally, I felt terrible for the Bilson character, a seemingly naïve college student who believed this man really cared about her, believed he was leaving his girlfriend, and believed she wasn’t doing anything that bad.

On the second viewing though, I basically found her to be Darth Vader. Just completely evil. This girl was scheming, conniving, manipulative, and freaking dangerous.  She knew exactly what to say to get her way. She also knew this dude was very much taken and not going to not be taken without her pushing the issue. So, she did all the stuff that gives us girls a bad name. Pretending she is fine with a situation she is not fine with, then acting crazy when she doesn’t get her way.  She was something out of The Hills—a frightening Kristin Cavallari clone who revels in manipulating people and situations.

If you’re reading between the lines here, I am officially a chick in her 30s who realizes how difficult it is to compete with girls in their 20s who learned all those girly lessons Dolores never taught me because Dolores didn’t know a damn thing about how to get a guy to do what she wanted.

If you’re reading between the lines of this whole post, what was an awkward first date in 2006 was a life lesson about why so many of these first dates didn’t pan out over the past eight years. It was some reassurance to us girls that the problem isn’t always that we aren’t good enough. It was a tragedy of why relationships can be so hard. And it was yet another reminder in a recent string of reminders that, as I get older, things that used to make no sense at all can suddenly become crystal clear.