Wasting Away In The Friend Zone

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I have no problem with the Friend Zone. The Friend Box. Friendship Island. The Vortex of Platonic Optimism….

Whatever you want to call it, I think opposite-sex friends are splendid. They can be an arsenal of insight when we need help understanding, well, the opposite sex.

What’s not so splendid is the opposite-sex friend who desperately wants to be more than friends. Especially when the opposite-sex friend who desperately wants to be more than friends is….


Oh, how I hate Me when Me gets Myself into that rut.

Years ago, I had a classmate, “Holly.” She had just moved to Southern California, and I was one of the first friends she made here. I think she gravitated towards me because I was already familiar with the city. That, and I also threw parties. Lots of them. If friends were crack, then my apartment was her pipe, and she’d show up at my place whenever her social life needed a fix.

One night, a group of us set aside our rampant partying and went out clubbing instead. Late in the evening, Holly and I found ourselves separated from everyone else. In a fit of drunkenness, we somehow started making out.

Over the next few days, I realized that I wanted to be more than just friends with Holly. So, I did what any rational non-eunuch would do: I asked her out.

Unfortunately, she confessed that while she enjoyed our impromptu kissing session, she wasn’t interested in dating me. Pretty brutal rejection, right?


She continued to call me almost every day, and we started spending even more time together, to the point where we were hanging out four or five times a week. And so, my crush continued to grow. Yes, I totally know what you’re thinking right now: “Well, of course, you dumb-ass.”

The problem was, her still wanting to see me only made it more difficult for me to accept how romantically not interested she was. She even referred to me as her best friend. Her best girlfriend.

Now, did I have an issue with this blatant emasculation?

Nope. I was so far from caring, the pet store in my heart was plumb out of rat’s asses. I was just happy that she wanted to spend all her free time with me. And this is where the “desperate” part of “desperately wants to be more than friends” weaseled its way onto me.

I became relentless in my pursuit. I bought her wonderfully thoughtful gifts. I took her out to fancy restaurants. When she had to work late, I brought food to her office. I left roses on her car. I took the grandiose romantic movie gesture to stalker-esque levels of persistence.

You see, I failed to realize that the grandiose romantic movie gesture only works when she loves you already, but just hasn’t realized it due to 1) a massive misunderstanding, 2) a massive miscommunication, 3) a massive mistake, 4) a massive combination of the previous three, or 5) the writer not having run out of plot devices to prolong the suspense. Worse, the grandiose romantic movie gesture ends up being totally creepy if she doesn’t actually like you.

I made it ever so clear that I wanted to date her. And she made it ever so clear that she didn’t want to date me. I’d like to believe that at least I was charming in my persistence, and maybe that’s why she still wanted to hang out with me (or maybe I was just that much fun to hang out with). Even so, how she put up with my all-out bombardment, I have no idea.

I even joked that I would eventually wear her down.

Well, she never did wear down. But, we continued to be friends. Until….

Several months later, she met another guy. One she was actually interested in. And, of course, she started spending more and more time with him. Soon, she started blowing me off completely.

When I figured out why she was blowing me off, I realized that I was only a placeholder. I was there to keep her occupied until she met someone she wanted to date. I know she didn’t do this on purpose, but that was the inevitable result.

I, of course, was devastated. And not surprisingly, we drifted apart. We haven’t spoken in years now.

Looking back, I have nothing but regret for the brief friendship that I had with Holly. As wondrous as Friendship Island was, it was still surrounded by the Great Barrier Reef of Frustration. With soul-devouring sharks patrolling the waters.

Just being around Holly destroyed my self-esteem. Yes, she had become my best friend. But ultimately, there was only one place my feelings would end up: utterly quashed.

Today, I can only promise myself that I will never make the same mistake again. I don’t care how good a friend she may be. I don’t care how often she calls. If she sees me as a platonic friend, but I want more, the friendship will never last.

And if I have a female friend who’s interested in me? Well, then I’m not going to be her friend. I’m not going to hang out with her one-on-one. There’s just too much potential for hurt feelings there.

Staying friends with someone you’re desperately in love with is like trying to get drunk on alcohol-free beer. Sure, you can practically taste the buzz. But, trust me, you’re never gonna get there.

Again, I do absolutely believe that men and women can be friends. But, with one enormous caveat:

They must both feel the same way. Only if both the man and the woman see each other platonically will the friendship be viable.

For a few brief months, Holly and I were best friends. Platonic best friends.

Not. Worth. It.

Never again.

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By day, I engineer happiness at WordPress.com. By night, I am a relationships and comedy writer, which can be redundant or an oxymoron, depending on your perspective. I am the creator of Musings, the blog you're reading right now, and LemonVibe, an anonymous relationship advice site. You can also find me on Twitter (I am not the creator of Twitter).

70 thoughts on “Wasting Away In The Friend Zone

  1. Hey Dennis, I just stumbled on to this article and I’m a little surprised. This is the exact same situation I’ve been dealing with over the past year (Being called her best friend and all). When she shot me down I was glad we could still be friends, but then she wanted to hang out far more frequently, and obviously I was (and still somewhat am) delusional enough to think that the more time I spend with her the more likely I’ll be able to win her over (I know, I know). towards the end of the semester we were getting lunch and dinner 4-5 days a week. Now that I’ve graduated and moved back home I’m hoping to finally move on, though I get about a dozen texts and snapchats from her a day. Anyway, thanks for sharing this!

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