Wasting Away In The Friend Zone

Image by minifig via Flickr

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'm a marriage and family therapist. By night, I am a relationships and comedy writer, which can be redundant or an oxymoron, depending on your perspective. I'm the creator of Social Savvy Sage, a coaching service that focuses on developing social skills. I am also the creator of Musings, the blog you're reading right now. You can find me on Twitter. (I am not the creator of Twitter.)


  • Trying to do the right thing

    Hey, thanks Dennis for your reply. I was reading some of your articles as I have never come across this site before. I really enjoyed your Musings – made me think and made me smile.

    As my friend is kind-hearted but cannot be open with his feelings to anyone, I kept making allowances, figuring I owed him somehow for messing him around. I know you think I haven’t and I sort of agree – he should have said something to me when he had the chance but I should have been less worried about looking foolish and just talked to him – immaturity I guess!

    But as I’m kind of independent by nature, my natural instincts have finally kicked in and I thought “Enough”. Just wanted to check that there was no other way to handle the situation – so I’m grateful for the validation. Thanks also for telling me I’m not being an over-sensitive girl – that was the part I was most hung up on in case I was being unfair. I discussed the situation with my husband, hoping to get a guy’s perspective. My husband said that that’s just my friend’s way – that my friend is not the type to talk about his feelings and he was not trying to be hurtful but just joking around and if I was ever in real trouble my friend would be the first to help. He’s probably right but my husband is the type to be fairly open with his feelings and he also thinks my friend is honourable for not trying to spend time alone with me and my husband trusts me 100%. Sigh…nothing is ever simple when figuring people out – but I tend to agree with your main point – why let my friend think I will put up with the hurtful, “unfriendly” comments. So I’ll forget about all the angst 🙂 and stick to simple behaviour-consequence logic. Thanks.

    • No problem. Glad you agreed. 🙂

      All things considered, I think it’s better to be slightly too sensitive than not sensitive enough. We are social animals, after all, and it’s important to recognize how others around us are feeling.

      At the same time, the more sensitive you are, the more likely you will feel guilt. I do wonder what it must be like not to have any compassion. Life must be so much easier….

      In any case, I suppose you can just take a “cooling off” period and talk to him again after some time has passed. From my experience, though, when dealing with people who aren’t comfortable talking about their emotions, you have to be VERY blunt. And VERY not nice. Something like:

      “Look, I the love the funny things you say, but I do NOT appreciate comments like [insert specific examples here]. You may think you’re being sardonic, but comments like these are hurtful to me. I’ve mentioned this before, and you seemed to understand. But after awhile, you started making them again. So, I’d like to ask you again, please DON’T make comments like these, because, frankly, they make me not want to talk to you anymore.”

      If I may presume to offer unsolicited advice, that is. 😉

      Oh, and….

      Sigh…nothing is ever simple when figuring people out

      Yes. That’s exactly why I started this blog. 🙂

  • Trying to do the right thing

    Ha, ha – hey if unsolicited advice makes sense I’ll take it. Thanks. I’m kind of taking the coward’s way out and hoping his pride will kick in and he won’t contact me as I haven’t written to him, because that would be less angst for me (even though I miss him) – it really hurts when I let my guard down, think he’s my friend, am all nice to him and I get a kick in the teeth. I start thinking he doesn’t want to be friends so I leave him alone and he emails me. So yeah – I’ll tell him your speech if he ever emails to chat to me again – he’s not due in town for at least the next couple of months and I guess trying to be his friend was a stupid move on my part – as you said guys have guys as friends, not girls (even tom-boy girls). But I hope I don’t end up looking like a drama queen LOL. I’m off to read some of your other stuff now for sage advice 🙂

    • Well, see now, if he kicks you in the teeth, then you just have to kick him right back. In the crotch. Twice as hard.

      Then turn him around and put a heel to his ass, too. 😉

      Just to clarify, though, I do believe men and women can be friends. I have female friends. Lots of them. (All the female writers on this site, for example, are women I consider to be friends, and I’ve known some of them for… yikes, decades now.) The only condition is that both parties have to be on the same page as far as the boundaries of the relationship go.

      At the same time, I believe there are those who just don’t know how to set these boundaries and therefore should not try to maintain opposite-sex friendships. Sadly, this guy might be one of them.

      And thank you again for reading. I’m always glad to help! 🙂

  • Hey Dennis – just wanted to give you an update. I’ve changed my name on here because forget “Trying to do the right thing” -I am too busy laughing at the fact that I have been totally played! I’m originally from Asia and have lived in London my whole life (hence the English spellings of some words)so I’d never even heard the term the “Friend Zone” until I Googled the question about why a guy friend would be mean to a girl. The answers eventually led me to your article. What I read on here got me thinking and I Googled some more and got to all kinds of US sites that tell guys how to get out of the friend zone, or why women prefer certain aspects of “jerk” behaviour to “nice guy” behaviour and the type of jerk behaviour that will have women chasing you. And guess what, I recognized a whole bunch of stuff my “friend” has been pulling on me. He’s very intelligent – he’s a director and has a really well-paid job in IT for a huge global bank in the US. The funny part is I realized when I met him after all these years that he had undergone some kind of transformation from “nice guy” geek to somewhat of a babe-magnet and I was happy for him.

    He was doing a good job of having me fooled but I think his mistake was that while he was doing some “truth disconnect” thing (see I remember the terminology on your US sites), he made a comment that he would “have to give [my cousin] some pointers on how to tweak me”. At the time I was too pissed off at why he would want to tell someone how to “tweak me” to figure out the implications of that comment until I did the research on the internet. I am not sure if he just wanted to pay me back or mess with my head for fun or because he wanted to get me to regret not picking him 17-odd years ago, or if he was actually trying to get me to cheat on my husband and have some kind of fling with him (but on his terms). I guess if I had been younger, more stupid, less confident, less principled, less cynical his unpredictable, challenging, sometimes attentive attitude might have got him somewhere. And although in my heart I’m a total cynic I have to give him the benefit of the doubt I suppose and assume he wasn’t looking for a fling – innocent until PROVEN guilty. I swear I must be as sick in the head as he is since I am torn between laughter and annoyance. I think laughter is best – I do kick-boxing and can punch bags and break boards with my bare hand…so I think it’s best if I don’t follow through on your suggestions on what to do to him 😉

    Well, just wanted to give you some food for thought on your musings of how messed up we all are – clearly we’re totally f***ed up ha,ha! And one final point – clearly acting like a “jerk” doesn’t work since I didn’t want to put up with that kind of crap but there were lots of changes he had made to his attitude that do work – he just needs to try them on someone who is actually available 🙂

    • Yeesh. Okay, now it makes sense. Sounds like he’s been familiarizing himself with pickup artist techniques. The subtle insults are known as “negs” and are basically used to pull down your self-esteem, so that you’ll feel like you’d be lucky to have him.

      Well, at least now you know, right? Sorry you had to put up with that.

    • Oh, incidentally, it sounds like he’s not even pulling the negs correctly. They’re supposed to be done in a light-hearted, flirtatious manner. They’re not supposed to come off as insulting….

  • So many wonderful metaphors. My favorite was comparing Holly’s need for friends to a crack fix. With poetry like that, I don’t know how she managed to resist you, friend.

  • Ugh. Twice. Thanks for bringing up repressed memories, guy. I was in love with my best friend for 5 years, and then later another best friend after aforementioned best friend took pity on my soul. Both huge, huge, HUGE mistakes on my naive part, both friendships ending tragically after a drunk decision to take it to the next level. Maybe it’s best you and Holly never did. If anything, you ended it on good terms whereas John, who for five horrific teenage years was my sounding board, my smile-in-a-box, my diary, my friend, my poet and my muse can’t even look me in the eye anymore. I’ll take your situation any day.

    • Ugh, sorry. I know it’s a horrible feeling. Maybe you just have to give him (or both of you) time to let the awkwardness fade? I wouldn’t give up hope on that yet, for what it’s worth….

  • It took me forever to finally get to read this, Dennis! Reading this, I feel horrible..I was actually “that” girl several times. I can say that I really did have myself convinced that I was just being nice and didn’t want to be arrogant enough to assume some guy wants me “that way” when actually maybe he’s just being a sweet friend…? Yeah..I know…ughhh on me:( Usually it was situations where I really did enjoy hanging w/the guy, appreciated the gifts and kind gestures, and was totally selishly afraid to tell the guy point blank, “never gonna happen pal” because I was terrified of losing the friendship I valued and wanted to stay in la-la land where I had this *fantastic* friendship! This article makes me feel liike shit. I suck…
    On another note, very informative about the guy friend being n insulting jerk to his girl-buddy up there… I’m going through that crap w/a guy friend right now and it gives me a better understanding about *why*…I just couldn’t understand the snide comments and put-downs…
    hmmmm, but putting it all together, I’m thinking maybe I deserve it from allowing this “friend zone” thing to happen so many times?! geesh, I’m all in turmoil here…. I’m sorry already, okay??!??

  • Just wanted to say i can relate to your experience, but it was even a little harder for me because the guy i had the crush on was flipping between 2 of my friends. So it was as if i was the friend island surrounded by this odd triangle. Still, it was the first time i ever felt that way about anyone, so it is it’s own learning experience, even if it was rather painful. I have been over it for a while, and i have a good laugh about how i acted now and then.^^

  • bloody hell..
    that was like reading the current chapter in my life… It does wear you down so much… Also instead of being some random guy who she ends up being with its one of my best mates…

  • I’ve worn your shoes dennis.

    Both as the guy who does the doting over the girl and as the guy who get’s a lot of doting and doesn’t want anymore.

    As the doting guy my difference also had a long distance component (met overseas then both flew away and stayed in contact online) which blew up when we finally flew back together again.

    I was the one been fawned upon in the aftermath because I really wanted to find out what that attention felt like and it was given away so freely.

    Moral of the story love hurts.
    So yeah been on both sides, both learning experiences where heart’s get hurt.

  • Aw man. I’ve been Holly, probably more times than I care to admit. Part of it is this hope, along with some deep denial, that maybe the guy in question will go away for a little while and then get over it so we can be friends again. This is dumb of me. Ah Me, how I hate Me when Me gets Myself into that rut too.
    Soooo… thanks for making me feel slightly bad about how I’ve treated friends, and while we’re on it, actually thanks for the blog. I’ve seen a few entries and been very impressed with your clear thinking and honesty. You seem cool.

  • 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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