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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  • Hmmm, not sure how much I agree with you here. I see the benefit, but as someone who has been hopelessly in love with their best friend (who due to geography I’ve drifted apart from), I can say that sometimes it’s worth it.

    • Fair enough. At the same time, your “issue” with this friend is still going on, right? If so, I think that’s the difference right there.

      As Jasmine’s Friend Box article demonstrates, sometimes persistence does pay off. In that case, then of course, it was worth it.

      In my case, persistence didn’t pay off. So, that’s why it wasn’t worth it for me. In your case… well, we still don’t know.

      So, maybe the secret isn’t so much just to write off any friendship as to learn to recognize which ones might be “worth it” in the end and which ones might not.

      Easier said than done, though, I’m thinking….

    • Oh no, different guy. We’re pretty solidly just friends now.

  • Eh…I’ve had a desperate crush on a guy friend before. It does help if he’s not your absolute best friend, and if he’s never encouraged your puppy-like devotion in any way (and you suddenly realize, when you view the mountain of responsibility you unwittingly agreed to, that somehow, you’ve been had, and you didn’t even get cookies for it)…Or if, say, even though he might be your best friend, he’s completely oblivious to your crush and you fully accept the futility of it all, and by the time you ever confess that such a crush existed, you’ve completely moved on.

  • Wow, that’s rough. I’ve never had a full-on case of unrequited more-than-friends-desire but this does remind me of a previous crush which was similarly futile. Another big drawback of getting caught up in that situation: while pursuing an unattainable acquaintance, it’s all too easy to forget to pursue anyone else! Maybe sometimes having the other person find someone else is the only way to break the spell.

    • Oh, yeah. What I failed to mention in the article (since I figured I made myself look enough like a tool) was that, in the midst of this crush I had on Holly, I kinda screwed over two other girls I briefly–and very half-heartedly–attempted to date.

      Ugh. Not one of my finer moments.

  • This reminds me of a Mumford and Son’s lyric: “you desired my attention but denied my affection.” Unrequited love is a bitch, and I am happy to hear that you have learned from your past (yes, flowers on your car is uber creepy. Even if I liked you that would be a red flag!)
    But still, my husband would disagree with you on one point: sometimes, you can wear a woman down.
    Just don’t creep ’em out first!!

    • Oh, I know. Looking back, my behavior was all kinds of creepy.

      What still baffles me is that Holly actually seemed… well, “touched” by my gestures and never said that they were inappropriate or anything like that. This, of course, only encouraged me to keep going.

      Meh. I still don’t know why she put up with me.

  • Another good one, Dennis! And again, (warning, dead horse beating ahead…) another reason you and I will probably ALWAYS be friends! It is actually a GOOD thing. Luv ya, Friend.

  • So, it’s kind of scary how much this story resembles mine. I have to say, it sucks being replaced. I’d already accepted the fact that nothing was going to happen, and then he got a girlfriend and I was pretty much out of the picture. As much as you can blame yourself for being a bumbling idiot in love, it’s not exactly nice to string someone along and then drop them completely. Kudos on the attitude about hanging out one-on-one.

    • I wouldn’t say that she dropped me completely. It was more of a gradual fade-out. But, honestly, at that point, I realized that hanging out with her when she was seeing someone really was not a pleasant experience for me….

  • I have a crush and the likelihood of it turning into more than friendship is something that I try not to think about much; distance and time, among other things don’t leave much room to consider anything more on my part (and I am not sure of his feelings either). That being said, I would not consider the time and feelings spent a waste of time because I’ve gotten to meet a great person and made tons of happy memories along the way too. Is it frustrating at times? Yes. But, for me, any possible outcome would have been worth it.  

    • Yeah, that makes sense. As long as you have happy memories, that’s the important part.

      I guess, for me, the problem is that the unhappy memories outweigh the happy memories.

      There’s actually more stuff that happened that I didn’t mention in this post. Maybe I’ll address it in the future….

  • On one hand I think it’s sweet that you kept trying, on the other… putting myself in your shoes rather than Holly’s, it just sucks. I’ve been Holly, but I’ve never been in your shoes, but I imagine it really sucks.

    Remember the guy I wrote about from my past that is happily married now? That only wants to be friends from a FAR distance? The one that got away? He was you so to speak. He was my friend that did all that and I was too young to see what a great guy he was. It’s interesting the perspective age gives us. Great article, I’m glad I can see it from the other point of view now.

  • I have experienced this but certainly more from the viewpoint of the guy liking me a bit too much although trying to stay as lowkey about it as possible. I have tried like the dickens to separate myself from 2 that still are in my life to some degree and have told them much the along the same lines as the song lyrics above. They love my attention but do not want my affection. For me this is a theme in my life which is my own fault partially, I see the part they are missing and I play to that void. It is the one instance where I stop being predatory and became more nurturing. I believe the dynamic is difficult and there are ways to manage it if you wish to have the person in your life because you value them enough. As for the two in my life, I assume it is only a matter of time before they stop being my friend and answering texts, reading my blog, etc when a girl they truly like enters their life. So far it has been over a year, they still are actively in the picture despite me trying to speed up what I believe is their eventual fate…dust in the wind 🙂

  • I’ve experienced both sides. Being the one who gets “crushed” is absolutely no fun.

    But on the other hand, you totally *know* when someone has a crush on you. And the way I see it, this whole thing is really her bad: she led you on, she accepted your thoughtful gifts and still continued to let you give your affection to her and did not reciprocate (and probably had no intention to ever reciprocate.) I don’t know if it was a mistake of youth, “Holly” having low self-esteem that craved the boost you were giving her or a case of this chick just being cruel. But do you really regret the *whole* relationship? There was a lesson learned, and I think that always makes it worthwhile (even if it was a totally sucky experience!)

    But I hope that you find someone who values you! You’d be a great boyfriend, I think! 🙂

    What a timely post, Dennis. I’m about to meet up with someone tonight to tell him that I met someone else, and that our relationship is going to be strictly platonic or non-existent. I have a feeling I won’t see him again after tonight…

    • Thanks… uh, “girl.” 😉

      Yeah, looking back, the most confusing aspect of it all is that she was so okay with the attention and affection I lavished on her. I mean, one can only hear, “awwww, you’re spoiling me” so many times before one starts hoping that, gosh darn it, maybe she will come around….

      But, yes. Sadly, I do regret pretty much the whole relationship at this point. I gave so much of myself to be friends with her. And, worse yet, as Matt mentioned above, I missed out on several “opportunities” that I might have had had I, well, been open to them.

      Good luck with your talk tonight. Honestly, if you don’t see him again, I think it’s for the best. For everyone involved.

  • It’s never quite happened to me the same way however I have a frined of 12 years that I’m still in touch with. We both married, she had kids (we’re still trying) She would have been my best man had I not been told to pick my brother! There was a point in my life were I believed that by not acting on my attraction to her (and I confess I’m attracted to most of my female friends)I missed out. She will always be the one that got away. We’re both happily married now, or at least working on it.

    • Hey, that’s interesting what you said about being attracted to most of your female friends.

      That’s kind of how I am, too, and I think it’s weirded out some of these aforementioned female friends. They’re, like, “we’re friends, you shouldn’t look at me like that.”

      Meanwhile, I’m thinking, “hey, if I enjoy hanging out with you, then I probably am going to be attracted to you on some level. Is that weird?”

      I personally don’t think so….

    • This is why when my husband and I got married we agreed to not have any friends of the opposite sex. I’m not saying I think everyone should do this, but for us it has made life simpler.

    • Hmmm, yeah, that’s a good way to do it. Too bad Holly wasn’t married. She would’ve saved me a ton of emotional anguish.

  • I had the same thing happen to me. Unfortunately it was my Best friend – WHO was a guy – who I had been friends with since I was five.
    We used to hang out every single week – He to me was awesome and my best mate who I told everything to, sat up late with, went out drinking with and just had a fantastic friendship with.

    He was also married.

    I never had any emotion for him apart from the fact that he was my mate and thats why I loved him.

    He took it upon himself to call me one night and tell me that he was “In love” with me. He was stone cold sober. My Response was not that of a delicate lady like person. It actually involved a hell of a lot of screaming – I was under the influence of a bottle of champers or two.

    Two days later he sent me a text and took back what he had said to me. He took back that he had said he loved me.
    I was accused of having an affir with him by his wife ( this was her substantiating why she had actually cheated on him – Basically it was ok for her to have an affair because she thought thats what we were doing.)

    I now no longer have any contact with him. He has tried on many occassions to rekindle this friendsghip,.
    But Im a Big NO.

    So there you go in response to your last comment about emotional anguish – Yeah um it doesnt count.

    • Yikes, that’s horrible. I’m sorry you had to go through that.

      For what it’s worth, I think you’re doing the right thing by NOT contacting him. He has to work out the issues in his marriage on his own….

  • I agree completely. It seems to me that she probably liked the attention you gave her. It obviously feels good when someone treats you well, dotes upon you, spends time with you. It’s a great time filler until you find someone who you actually want to be with (in which you will dote on them too!). I can’t see how she DIDN’T know she was using you in this way. I’m ashamed to say that I’ve done this before — not to the extent you are discussing, but still the same — but I knew exactly what I was doing at the time. What she should have done is told you that romantic gestures were not welcome because she was not interested in you romantically. Instead, she reaped the rewards of your love and didn’t give you anything in return. Coming from someone who has done this before, I can say it’s incredibly selfish.

    I agree with you 100%…. men and women can be friends, as long as it is truly plantonic on both ends. And, in my experience, that hardly ever happens for very long. Eventually, you are spending time together and enjoying each other’s company, and if you are both single, someone develops feelings. It almost can’t be avoided. It’s how those feelings are dealt with that decide whether or not the friendship can continue.

    Sorry you had to go through this, but it seems you are probably stronger off because of it!

  • Stars and garters, that’s worse than my tale. My sympathies.

    Though I have to say that over half my friends are the opposing sex/gender and there’s only been one time where someone (me) wanted to move beyond platonic.

  • I’m actually kind of irritated with this Holly person. As a gal, I can usually tell when a guy is digging on me (warning flags being the gifts and whatnot). I like palling around with guys, but if they start actively flirting or mooning over me, I make it clear I’m not interested (none of this, ‘Oh, you’re so thoughtful’ BS – because I know that’s just stringing him along).

    I just feel like she was using you to fulfill a vacancy in her life, as you mentioned, but I find that unbelievably selfish and very unfriendly. You don’t do that to a friend. If you can’t give the guy more, you tell him and let him move on. This makes me grouchy.

    • Hey, thanks for grouching it up on my behalf. In her defense, though, I really don’t think she realized what she was doing. She liked hanging out with me (which, of course, wasn’t helped by the fact that she didn’t have many friends in San Diego at that point).

      She just didn’t like hanging out with me as much as the next guy she met…. 🙁

    • I don’t buy it. I like hanging out with guys, too. But once I know that they’re into me, I make sure I put the brakes on. Even if it means hurting his feelings a bit and distancing myself. It just reinforces the notion that she liked the attention and was willing to hurt you in the long run – which I think sucks.

      I have no right to take advantage of a guy who I have no interest in being with. Granted it hasn’t happened a lot since I tied the knot, but occasionally I get the vibe. And the thing is, I KNOW what’s going on. I’m flattered and I LIKE the attention, but I know I need the distance. Because if I don’t then things move into the danger zone. And the danger zone isn’t just about me, it’s about the other guy too, cause if I let him think it’s okay to act like that, only to hurt him more later on isn’t acceptable in my book. Not to mention the cluster that could occur in my marriage if I let something like that happen.

      (I can’t reply directly to your post, Dennis).

    • Oh good. It still worked.

    • Yeah, you’re right, no matter what her intentions, it definitely sucked for me. I guess, the way I see it, I can’t go around counting on someone to treat me “the right way.” I have to look out for myself and learn to recognize when I’m in a bad situation. Then, I have to have the willpower to get the f@ck out….

    • This is an old thread, but I just wanted to say how encouraging it is to see so many women in the comments calling Holly on what she did — which was to selfishly string Dennis along because she liked the ego boost.

      Maybe I’ve been reading too many feminist blogs lately (where it always seems to be “boys vs. girls”) but it’s really nice to see that some women see this situation exactly the way I do. I couldn’t have put it better than Jaberkaty: “You don’t do that to a friend”.

  • If women are interested, they can’t help but show it. Asking a girl out when she has not show attention? Damn that something only someone profoundly ignorant of women would do.

  • Ha… I’ve been there Dong. One of my favorite guy friends in college… I was head over freaking heels for him. But he only liked foreign, exotic women. Apparently Appalachia wasn’t quite doing it for him. It sucked.

  • Thanks for sharing. I’m sad you had to come to this decision but I think it’s a good one.

    • Thanks, Rachel. Yeah, looking back, it was definitely the right decision to let our friendship wither away.

      At the same time, though, I also know that I probably wouldn’t have had the resolve to do it had Holly not met this other guy. Yeesh. I don’t even wanna know how long I may have gone along with the situation….

      Not my proudest moment.

  • Dennis, as usual, so well-said. I haven’t read through the comments, but I do want to say one thing… something that women especially will probably hate me for saying. But here’s the thing: Any girl who tries to stay “friends” with you, knowing how much you want to be more than friends, and all the while is accepting your gifts and other dotings and – I’m just gonna say it – ultimately taking advantage of how you feel, is not really a true friend at all.

    It’s happened to me in the past – a really great guy (probably not unlike you) who wanted to be more than friends with me, but I just didn’t feel it for some reason (most likely sheer stupidity). Not only was I extremely up-front about how I felt, but he never got to the “desperate” part of wanting to be with me because I never took the relationship that far. In fact, I backed off immensely – not because I didn’t want to hang out with him anymore, but I knew that doing so while knowing how he felt was extremely selfish. Like dangling a cookie inches from his face and telling him he couldn’t have it.

    I know that ending the friendship sounds cold, but it really turned out to be the best thing for him. Ultimately, I think it’s how I proved myself as top friend material, because he was able to romantically move on. Once he did, her pursued our friendship once again, and it was so much easier. So much better. And definitely very real. We are still great friends today, and I’m looking forward to his wedding next October!

    This is just a really long way of saying that no matter how great a girl seems, she’s not a true friend if she leads you on, uses you, or doesn’t respect your feelings. Plain and simple.

    Loved the article!

    • Thanks again, Katie. It’s nice to get sympathy on this one. I guess, for my part, I just don’t believe in playing the victim.

      Sure, we can say that Holly was wrong to take advantage of my feelings.

      But, at the same time, we can’t always count on others to do the right thing. So, it was my fault for letting her take advantage of me like that.

  • Trying to do the right thing

    I have never posted here before but I wanted to present a personal angle to the friend zone that shows that rather than being users, it is sometimes a case of women being inexperienced and not confident enough to confront a situation and also just trying to be nice.

    I had a close family friend – his parents and my parents go way back, who is about 15 years older than me and who I look up to and think is awesome because he is responsible, hard-working, takes care of his family, generous, kind, intelligent and humourous. He used to call me international on a regular basis but never said anything romantic – he just made the regular international calls and listened to me talk about parties I had been to and what was happening at university. I never called him back as I couldn’t afford to. I thought at the time that maybe he was kind of bored (I know on hindsight extremely dense of me) and I was kind of entertaining on the phone so maybe we were meeting each other’s needs – I never thought that someone like him in his mid 30s would be romantically interested in some irresponsible 20 something who was having a crazy time at university. I was and still am kind of a tom-boy so it did not occur to me that I couldn’t be friends with a guy. I was too scared to ask if his calls had any motive other than friendship – he doesn’t open up much and uses sardonic quips in place of real conversation so I really didn’t want to ask awkward question and be made to feel a fool, especially as he was a family friend who I would definitely run into in the future. I also did not want to imply that there was anything wrong with us being platonic friends or that I was so full of myself that I would get the wrong idea just because he was being nice to me.

    Now, 15 years after my wedding to someone else, the family friend (who has never got married) comes to my city quite a lot on business. In the past, he very infrequently and politely initiated contact if I was in his city to visit his sister, who I am close to. However, it was only now that I realized for sure that he had liked me as more than a friend all those years ago (he made a quip about it in a passing email) and I apologized profusely if I messed him around by taking his calls without telling him I was seeing someone else (the person who became my husband). I still think my friend is awesome for all the same reasons I liked him before and we joke around and tease each other like old friends – I have no problems with my husband reading any emails between my friend and me as they are not inappropriate, just banter. But sometimes my friend makes more hurtful, teasing comments and so recently I have stopped emailing him although I will reply if he emails me as I don’t want to hurt his feelings. I started wondering if I was taking his comments too seriously and that it was just his sardonic nature coupled with the fact that girls over-think things and guys don’t mean anything by what they say. Or were the thoughtless comments a reflex need to prove he doesn’t give a damn about me any more, which isn’t too much fun for me to be on the receiving end of. I think my friend is attractive by the way but I’m married (to a wonderful guy who I love deeply) so obviously I have nothing to offer other than friendship.

    My young kids love my friend and enjoy hanging out with him because he is such a great guy. I figured if I wasn’t asking him for anything (no gifts or doting not that he ever gave me any gifts or doted in the past), not hugging him or having any other physical contact with him, not confiding in him about my relationship with my husband, and I was just being nice to him – as a family we invite him out to dinner often or he comes home for dinner sometimes – as he is on his own in town, while simultaneously telling him he would have fun if he got a girlfriend, that I was showing him how well I think of him. I figured he wouldn’t mind being in the friend zone in this situation and that I could not be accused of taking advantage of him. Seems like all I did was screw things up by trying to be a good friend. I don’t know if he mistook my friendship overtures for interest and is worried that I want more than friendship.

    I did call him on his off-hand, hurtful comments a while back by trying to stay out of his way and he asked me via email why I was being frosty so I told him he was being hurtful and he apologized and improved for a while but then he started slipping back to his old ways. I don’t think I have any option but to stop being his friend, which kind of sucks for me as I miss his funny emails and sardonic perspective but I certainly don’t miss the “don’t gave a damn about you” comments in stark contrast to his kindness to everyone else. Sorry for the essay – but I needed to finally get it off my chest!

    • Hey, thank you for sharing. For what it’s worth, I think you are definitely doing the right thing and, in fact, never did anything wrong in your friendship with him. As you mentioned, you never reached out to him. You responded if he reached out to you. But you never took the initiative yourself. And that, to me, is key. That, to me, says that you never led him on in any way.

      I want to respond to a few other comments, too:

      I started wondering if I was taking his comments too seriously and that it was just his sardonic nature coupled with the fact that girls over-think things and guys don’t mean anything by what they say.

      That’s BS. Guys can be totally passive-aggressive. Since it’s not the “guy way” to show vulnerability, I think he’s just lashing out by making comments to suggest that you mean nothing to him. You’re not the first girl I know who’s had this happen with a guy friend.

      I figured if I wasn’t asking him for anything (no gifts or doting…), not hugging him…, not confiding in him…, and I was just being nice to him…, that I was showing him how well I think of him.

      And I think that’s exactly how you should treat him. I don’t think you’ve done anything to “screw things up” at all. He’s the one screwing things up, not you.

      I don’t think I have any option but to stop being his friend.

      I agree. No one should have to put up with hurtful comments, and I don’t think you should let him get the impression that you’re going to put up with that passive-aggressive crap.

      Look at it this way: are his funny emails worth the hurtful comments? Is he that good of a friend? Doesn’t sound like it to me.

      Anyway, I do hope it all works out. Again, though, I don’t think you should blame yourself for what’s happened.

  • 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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