Single-Minded: On Dating Your Best Friend

In the movies, dating your best friend always ends up in happily ever after. In real life, not so much.

Warner Bros.

The frustrating fact about falling for your friend is that it rarely works out like it does in the movies—like how it's supposed to.

Earlier this week, I went to see the celeb-riddled cheese fest, Valentine's Day because I like to be up on what Hollywood thinks passes for real-life romance, no matter how destructive that paradigm can be in 3-D. Isn't the first rule of combat “know thine enemy”? According to this latest cinematic fantasy, turning “a friend from someone that you like into someone that you love” is the quickest road to a relationship. And despite sounding convincing on the big screen, that type of advice—“Easy, I married my best friend!”—only works if your best friend, in fact, wants to marry you.

In the movie's main story line, florist Ashton Kutcher wants to hitch his wagon to girlfriend Jessica Alba, who plays something of a corporate Barbie Doll complete with Mattel-blonde dye job and unmovable BlackBerry. It's never made clear why Kutcher wants to marry the girl he defeatedly describes as “too good” for him, but they already live together, and she's hot and what not, so why not? The conflict here, of course, is whether Alba's career is more important to her than commitment. Then there's Kutcher's platonic gal pal Jennifer Garner, who's also in love with a to-die-for professional—cardiologist Patrick Dempsey, who's got his own commitment issues. All this in the first 10 minutes. It took the film another 115 to tell the audience what we already knew.

To be fair, it probably wasn't the most unbiased idea to go see Valentine's Day the same day “things” ended (for real this time) with “Jake,” a friend-turned-flame-turned-foe. After being in “more than a working relationship, but less than a romantic relationship” for the better part of a year, it became clear that I wanted more than dating-lite, and Jake was on a strict, no-commitment diet. I get that. That's OK. Really. Everyone is entitled to their own litmus test when it comes to whom to cling to and whom to cut loose. What's troubling, for me, is that this has happened before with a small but steadily increasing tab of former friends that once fit the bill of possibility.

Forgive me for quoting this week's Internet villain, but singer/over-sharer John Mayer was on to something when he recently told Playboy magazine, “But that pearl of possibility that lives in your heart when you meet somebody you want to know more about has such a different molecular density than everything else that you have to pursue it. And I wouldn’t undo it, man. Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, ‘What I have when I go home is the thing I’ve always wanted.’” That's exactly how I've felt time and time again about a good friend—“a pearl of possibility” disguised in the platonic. Someone about whom I could say fondly, “Well, as you all know, at first we were just just friends.”