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.”

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First there was “Dex,” who referred to me frequently as Perfect Girl. That was my code name, or perhaps my nom de guerre, among his friends. When he told me this, I knew we were done for. His perception of my alleged perfection was based on our “friendship,” on my “coolness,” my inherent “otherness” compared to all those other girls. I was different, and therefore doomed, because actually—I wasn't.

The truth was, I was just like all the other girls who wanted to hold his hand at Pentagon City Mall while vetoing too tight jeans at Express Men. I was just like the rest of them. He just hadn't noticed. My coolness, my alleged gleaming perfection, had given him snow-blindness. But instead of heading for the door after Dex's late-night confession, I forced myself to snuggle up to the rented space between his bicep and his pits, breathing in the stink of another relationship gone bad. Perfect Girl? I gave us another month. Two, tops. And I was right.

Then there was this latest buddy, Jake—an old friend I met through older friends, who after several thousand lines of Gchat, finally delivered a gem: “I have two moods: happy and pissed off.” Lust. Ignited. Actually, it was Frances, my mother, who lit the match, describing him twice as having a “nice build,” which obviously grossed me out at first and then at second made me think. Soon I was spending an extra 10 minutes in bed every morning, fantasizing about this nice build of his and how it would look, um, erected. I sent out a new boy e-mail alert to my girlfriends with the disclaimer that nothing could ever really happen since we were in the friends zone—the danger zone.

Eventually we would get over that hurdle and I would allow myself to hope, if not for a ring, at least for a standing Saturday night engagement. How quickly hope deflates at the sound of “we don't have the same expectations.” Which isn't to say my heart doesn't still believe in movie magic. Or that I can suspend that belief wholeheartedly.

I’m fully aware that what happens on celluloid isn't always safe for popular consumption. That perhaps buying into the “best friends forever until they're not” (BFFUTN?) meme could all just be a setup for failure because the person “right under your nose” might not smell so great up close. The probability of picking a sure thing? Uncertain. But if La-La Land can offer us anything, it’s “promise … ignorant of reality” because “if it had worked out, I would have reaped the benefits.”

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Helena Andrews is a regular contributor to The Root. Her book, Bitch Is The New Black, will be released this summer. Follow her on Twitter.

Helena Andrews is a contributing editor at The Root and author of Bitch Is the New Black, a memoir in essays. Follow her on Twitter.