How can I be a true friend to a guy whose romantic feelings I don't return?

March 21, 2012 7:13 AM

My dear friend, to whom I am not attracted, continually brings up wanting to date me and isn't getting what I thought were my polite expressions of interest in being just platonic. I think I need to tell him in no uncertain terms, but am not sure how, due to the special snowflake details below.

My friend is a kindhearted soul who does many things for the small community in which we live. He's bailed me out of several jams in the past year and I appreciate him a lot, not just for that, but for his intelligence, warmth, and sense of humor. He truly is a fantastic person and I value his friendship a lot.

However, he's brought up liking me as more than a friend several times, and I've politely passed it off as just flirting, or deflected it somehow. He is an extremely rejection-sensitive person and he's told me enough that I know he'd be very hurt to hear an explicit explanation that I am just not physically attracted to him. He already feels undesirable due to some unpleasant experiences in the recent past including a huge betrayal by his ex that led to divorce after decades.

I just don't want to hurt him! He's done so much for me and all I want is to give back...but platonically. I have begun to feel like I'm taking advantage of him by being the recipient of his generosity. (He has offered help and I've accepted; he does such things for everyone he knows).

I also feel a little awkward, like he's been my friend for the last year because he's been waiting to have a shot at dating me. It makes me uncomfortable.

The last time this came up it was during an online chat and he got really embarrassed and left the chat, in which he had said he wanted to talk to me about the possibility of dating but then a few lines later said he was feeling embarrassed and didn't want to know the answer.

I in turn felt embarrassed and am worried that to continue the friendship will just hurt him if he's pining for me and all I want is to be seen as a sister to him.

I could simply distance myself, but I think that kind of sucks. He's been so awesome (except for bringing up unwanted discussions of romance).

I have a lot of reasons why, to me, he and I are incompatible, but my lack of physical attraction is the top one and I just feel terrible about it. Unfortunately, it's not just a "meh" feeling. I am actively turned off by certain aspects of his physical presence. I'm afraid that will come across and I fear he already thinks he is ugly. I so don't want to be someone who reinforces that.

Should I just act normal and address the subject next time he brings it up? Should I say something now? If so, what the heck do I say?

posted by anonymous to human relations (49 answers total)

He is trying to Nice Guy his way into your heart. If you're not into him, you're not into him and it won't work. And he needs to realize that.

Your situation kind of sucks because what a lot of Nice Guys need, ultimately, is a hard kick in the direction of being confident and direct rather than fearful and passive, but ultimately you're not in a position to give him that confidence.
posted by gauche at 7:20 AM on March 21, 2012 [27 favorites]

Subtle is only nicer as long as the person is capable of 'getting' subtle. Once they haven't gotten that, the nicest thing you can do is telling them directly. As much as you appreciate all he's done, there's a fair chance that he's doing these things because he thinks of you as more than just a friend, and you shouldn't continue to take advantage of his generosity as long as there's any question at all in *his* head about where this is going.

You don't have to tell him that he's revolting. You can just say, "I've noticed you seem really interested in me, and I'm flattered. It's just that I'm not attracted to you and I don't want to have a relationship with you, which is really just a matter of personal taste, so nothing is going to come out of this along those lines, but I value your friendship." He's going to be very hurt, but that's just because these things hurt. It happens. Let him make the decision about how he feels about this fact. It's a fact, whether or not you've told him.
posted by gracedissolved at 7:21 AM on March 21, 2012 [8 favorites]

I have a lot of reasons why, to me, he and I are incompatible

This is the key. I think it is fair to him to tell him when it seems right (which would probably be if he brings it up again). If he does, just tell him that you value his friendship and see him as a great friend, but there are a lot of reasons why you would be incompatible as a couple. You can refrain from saying the reasons that would hurt him while making it clear that this is how you feel and it's not going to change.
posted by DoubleLune at 7:21 AM on March 21, 2012 [2 favorites]

I have a lot of reasons why, to me, he and I are incompatible, but my lack of physical attraction is the top one and I just feel terrible about it. Unfortunately, it's not just a "meh" feeling. I am actively turned off by certain aspects of his physical presence. I'm afraid that will come across and I fear he already thinks he is ugly. I so don't want to be someone who reinforces that.

First of all, he DOES NOT need to know this!

I definitely feel you and have been in your situation, but here's the thing: as women we are told that we need to be nice and not hurt peoples' feelings, so that's what you think you're doing by not addressing this, but... you are hurting him by not being firm. He doesn't want to believe you'll never date him, so he will ignore all evidence to the contrary until you sit him down and spell it out for him.

Just phrase it as- look, I like you a lot, but I don't see myself ever dating you, because I don't think we would be compatible as partners. If you're ok with being just friends, I'd like that, but if you can't deal with only being my friend then that's ok too. And don't let him argue with you! Stand your ground. I'd also recommend either doing this in person or sending him an email, because he has proven that he'll just quit online chats when this comes up.
posted by showbiz_liz at 7:22 AM on March 21, 2012 [9 favorites]

Should I say something now? If so, what the heck do I say?

"Look, I value our friendship, but it will not progress past that. If you value our friendship as well, please don't bring up dating anymore because my answer is not going to change and it will only make things uncomfortable for both of us."

He doesn't need to know that you don't find him physically unattractive. If he pokes and prods about whyyyyyy, you might have to abandon this friendship. Not because telling him would hurt his feelings, but because the sort of person who does that can be troublesome in the long run (i.e. do you really want to end up on the receiving end of a Grand Romantic Gesture from this dude?)\egardless of all he's done for you, it doesn't give him the right to make repeated and unwanted romantic advances.

Also, please don't get down on yourself for not finding him physically attractive. Unless you're the sort of person who won't give the time of day to anyone who couldn't be a runway model/athlete/rock star/whatever, attraction is a matter of taste. If you couldn't stand fish, would you feel bad for not liking sushi? If you hated horror movies, would you feel bad that you couldn't enjoy Nightmare on Elm Street? Probably not, no. Same thing. You don't find him attractive and that's okay.
posted by griphus at 7:24 AM on March 21, 2012 [13 favorites]

Wow. I know someone who could've written this word for word, except for the parts about an ex, a divorce, and decades. I'm on the other side of this situation. My friend feels pretty much the same way about me as you do about him.

I only have one piece of advice: Be firm. Say you're not interested. It will hurt, but (hopefully) he'll get it. If that doesn't work, the best thing to do (for both of you) is to stop talking to him.
posted by retypepassword at 7:25 AM on March 21, 2012 [1 favorite]

Well, of course you will NEVER EVER tell him that his physical appearance turns you off. That's not a cool thing to say.

But you're not a whore. You don't have to feel obligated to do anything other than be nice to him just because he's been nice to you. And nice doesn't mean lying to him.

I say take the bull by the horns and tell him what you should have told him before. That you don't have anything to offer him other than your friendship. If that's not enough, then you're sorry. You do NOT have to go into detail why other than you're just not feeling it. If he asks for more, don't engage that conversation.

And do it proactively because honestly, every time he thinks about you or is with you, he's thinking about dating you. It's in the air. It's out there. It's not fair for you to allow that thought to remain a possibility in his mind when it is not.

Be clear. If he can't read subtle, that's not your fault. He needs clear. Give it to him.

And, of course, we all hate to be rejected. He will get over it eventually and he will find someone new to pine over in time, I'm sure.
posted by inturnaround at 7:26 AM on March 21, 2012

"I've noticed you seem really interested in me, and I'm flattered."

DANGER WILL ROBINSON. Saying something like that to a persistent person -- hell, even including "I'm sorry but..." in there -- may just serve to encourage them. We don't know enough about him to say whether or not it will, but you really just want to avoid any sort of acknowledgement of the fact that you're cool with him trying to charm you.
posted by griphus at 7:26 AM on March 21, 2012 [16 favorites]

You are hurting him already by stringing him along. You could drag it out, which would be long and painful, or you could make it quick and get it out of the way.

The next time he brings it up, you need to tell him that you appreciate the attention but that you don't think of him in that way, and you are not interested in being more than friends with him. Explain that attraction is not always a logical thing and that this isn't something you're going to be argued into or out of or whatever: you've thought about this and you do not want to be more than friends with him and it's not something that is going to change.

Don't say exactly why. He will feel unattractive and discouraged no matter what you say, but it's better he feels that way now and has a chance to move on than having it slowly ground into him by dint of failure to receive a direct answer. He doesn't need to know that you're turned off by him. He doesn't need to know any reasons at all.

Don't put it in soft language; don't say you're not attracted to him right now, don't say that you wish things were different, don't say anything like that. Be concrete. Be firm.

Inform him that you understand if he needs space to get over this and you will make whatever accommodations he needs, but when he brings it up it is making you uncomfortable and that it needs to stop.

Some of the worst harm that has ever been done to me in relationships was done by people who thought they were being nice. Just tell him. It's hard, but the alternative is worse.
posted by FAMOUS MONSTER at 7:26 AM on March 21, 2012 [4 favorites]

I've been the one with the unrequited crush more than once, and so I think I understand what he's doing here. He's carefully protecting this no-mans-land between being your platonic friend and explicitly asking you out on a romantic date -- he keeps sidling up to the critical moment, dropping hints and half-asking questions, but then backs down at the last minute before you can actually respond. While he's in this space, the possibility that he's misunderstood your signals -- that you WOULD actually date him if he asks -- still exists. Consciously or no, he's avoiding the moment where you're given a handy opportunity to explicitly reject him.

If my experience is anything, this could go on for a very long time if it's allowed to, a possibility which wouldn't be fun for either of you.

The next time he starts to drop those hints or almost-asks you to date him, you should probably take that opportunity to say -- kindly but explicitly -- that you're only interested in being friends.

As for the potential blows to his self-esteem -- you DON'T owe him specific reasons why you don't want to date him, and honestly, those reasons wouldn't be helpful to him anyway. If he tries to pry more details out of you, just keep it to "I think of you as a friend, I'm sorry" and leave it at that.
posted by Narrative Priorities at 7:29 AM on March 21, 2012 [6 favorites]

I know he'd be very hurt to hear an explicit explanation that I am just not physically attracted to him.

OK, you don't need to mention the particular why of why it's not going to happen.

But even if it's gonna hurt, you need to be Very Clear that it's Not Going to Happen. You tried being nice about it, but now it's time to be Very Clear.

The next time he starts flirting or being suggestive or whatever, simply stop and say "KNOCK IT OFF, PAL." He'll sputter a bit, but he'll get the message. And he needs to get the message.

Sure, it'll hurt. But being soft about this, and not being Very Clear, that's only going to hurt you both more in the long run.
posted by Capt. Renault at 7:29 AM on March 21, 2012

The kindest thing you can do is to simply say,

"Look, I'm just not interested in dating you. I really like being your friend but your repeated attempts at bringing up our possible romantic involvement is making me uncomfortable. It might seem rather harsh to just come out and say it like this, but I'd rather get it over quickly so you can focus your efforts on pursuing a woman who really would want to date you, rather than feel awkward about telling you no."

Saying it straight like this
1) Shows you respect him and don't want to play games, whatever his reaction
2) Acknowledges your "feeling awkward" and discomfort. This looks humbling, and shows you care enough to try to stay friends. Whether or not that's worthwhile is up to him.

Don't play games. Just stick with being honest.

If he seriously pursues why, then, yeah, say you're not attracted to him. If you dance around the topic and he guesses at what you're trying to avoid, you'll look like a scumbag.
posted by DisreputableDog at 7:30 AM on March 21, 2012 [17 favorites]

He doesn't want to know the answer because he does know the answer.

Because he fortunately has brought it up directly, you can send him an email saying, sorry, Nicey, but I don't want to date you. Maybe he wasn't direct enough before (I hope, because if he was, you should've been), but now he has been.

It may be tempting to reassure him of your friendship, but he seems like the type to take that as encouragement for years on end. I wouldn't hang out with him any more.
posted by tel3path at 7:30 AM on March 21, 2012 [3 favorites]

Some men are brainwashed by movies where putting in time and effort gets the star the girl in the end. You need to be firm and tell him that he is like a brother to you and you will never date him. Emphasize that there is nothing wrong with him or you, just that you're not right for each other. Be very firm, make it clear you are not joking around and will not change your mind. Keeping your distance from him would be good too, unfortunately it will need to be permanent because if you stop he will think there is hope again.

I hate movies and books that encourage men to not give up in this scenario, in real life it very rarely works (almost never), makes stalkers out of normal men, and undermines respecting what women say and feel.
posted by meepmeow at 7:30 AM on March 21, 2012 [16 favorites]

Don't know the etiquette on YouTube videos in comments, but this video about the "friendzone" might help (I'm not affiliated with it in any way).
posted by ataxia at 7:33 AM on March 21, 2012

I could simply distance myself, but I think that kind of sucks.

Do you have enough friends? Presumably the answer is yes. Hopefully the answer for him is yes, and he can say to himself, "it's never going to 'happen' with anonymous, so I should move on."

Most friendships, except the closest ones, have a limited lifespan. One of the reasons they have a limited lifespan is because eventually, what the people were getting out of the friendship is no longer there. If you no longer need his help and he no longer feels that spending time with you will lead to what he wants, then the friendship can gracefully disengage. Maybe there's some other reason you guys would make great friends, though, and if you manage to find common ground there, great.
posted by deanc at 7:44 AM on March 21, 2012 [1 favorite]

I should clarify - he should watch that video. He's probably not actually being a good friend to you.
posted by ataxia at 7:48 AM on March 21, 2012

I could simply distance myself, but I think that kind of sucks.

But it works. And I'm saying this from the perspective of someone who was put in the friendzone as opposed to the one who did the putting.

I'll admit I wasn't quite as aggressive as your friend, but I have a friend I've, er, "warmed up to" a couple times now over the past few years; there's been two times I've floated the idea, and he gently turns me down. And then -- for a couple months he's held me at arms' length to give me a chance to calm down a little.

And yeah, the first time felt a bit weird, but I was also feeling embarrassed and kicking myself and then realizing that "wow, though, if I kept seeing him every day I'd feel even more mortified, so this is probably a good thing," and...then in a couple months he'd gradually start hanging out again and everything was fine.

It works.
posted by EmpressCallipygos at 8:03 AM on March 21, 2012 [6 favorites]

"I was talking to a friend of mind about dating after a divorce, and about how helpful it is to have a platonic friend of the opposite sex as a 'dating consultant', to provide a second opinion about clothes and things like that. I know your divorce was really hard on you, but I wanted you to know I really appreciate the things you've done for me, and so when you're ready to start dating again I'd be happy to be your platonic 'dating consultant' -- let me know if you're interested in that."

Of course, you could always just offload the sense of responsibility for his feelings that are bothering you and get it over with by responding to his next advance with "You've been a good friend, and I appreciate you, but not every friendship can transition to a romance, just like not every romance can transition to a friendship. I'm not interested in a romantic relationship with you, and I hope you'll respect that." He'll have his feelings hurt, but that's a healthy thing in this case, as it will let him move on. Sometimes moving on hurts. But if you can't get yourself to say it outright like that, my suggestion might allow you to hurt him properly without feeling like you did it.
posted by davejay at 8:16 AM on March 21, 2012 [2 favorites]

You also need to stop making him privy to whatever life problems you're facing. You can't put him in the position of being there to bail you out. He's no longer that kind of friend.
posted by bonobothegreat at 8:16 AM on March 21, 2012 [8 favorites]

I have begun to feel like I'm taking advantage of him by being the recipient of his generosity.

You're not. If he thinks that because you accept his generosity you owe him a romantic relationship, that's his delusion. There's a stock character in pop culture, the bitchy high school girl who takes advantage of the boy who's in love with her. You are not that fictional character. You are not manipulating him. You are acting like a friend: a true friend both offers to do nice things and graciously receives the generosity of her friend. You may want to disengage somewhat if he reads more into your acceptance of his generosity than a healthy friendship, but you're not doing anything wrong.

Griphus's wording is great--firm in the way that it needs to be, nonspecific as to why you're not interested. He might ask why--he might even say, "It's because I'm ugly, isn't it?" And I think the thing to do is to be firm about the lack of chemistry. "It's not going to happen. I don't feel any chemistry between us. There's nothing wrong with you, but nothing you could do to change this."
posted by Meg_Murry at 8:17 AM on March 21, 2012 [2 favorites]

You're going to have to hurt him. He's giving you no option but to do so. No, I'll rephrase it: the option that wouldn't hurt him is for you to cave in, date him, have sex with him, and marry him. But if you can't stand that, and I wouldn't recommend that you do because he's such a Nice Guy...you're going to have to hurt him. He will be hurt no matter what you say here, you just don't have to kick him as hard by exactly saying that you don't want to have sex with him. I know you don't want to reinforce his thoughts that he's ugly, but he is going to go there mentally no matter what you say. It can't be helped. You can't date/have sex with/marry this man to help his self-esteem because that's sacrificing yourself to his needs. No, it won't help him any, but it has to be done.

He "knows" you don't like him like that, but he's clinging to denial very hard here, given his behavior. It sounds like he's edging around asking you out, and if/when he goes there again, I think that's when you have to have The Talk. Unless he totally hedges from now on, in which case it's kind of hard to bring it up without him doing it. But it sounds like he's bringing it up, so you might as well take advantage of it and drop the bomb as well as you can.

I honestly would tell you to drop him as a "friend" after you say no. You said you think he's being friends with you because he wants to date you? I think you're right. You can't be friends with someone you wish you were boinking anyway, really. At best it's going to be awkward as hell if you don't distance yourself, and I really do believe that having you around in his life fuels his fire and won't help him get over you.
posted by jenfullmoon at 8:19 AM on March 21, 2012 [7 favorites]

Yeah I mean it's worth mentioning that you may have to deal with a little resentment from him once it's done; some sort of palaver about how women don't want nice guys and how he does all these wonderful things for you but you take him for granted or whatever garbage like that. Remain steadfast. By telling him the truth you are doing the right thing. Feelings of guilt are entirely normal and are to be expected. They will pass. In any event they are better than the mounting dread you're feeling right now.
posted by FAMOUS MONSTER at 8:25 AM on March 21, 2012 [3 favorites]

You can't be friends with someone you wish you were boinking anyway, really.

Uh, maybe you can't, man.

OP:

When you break it to him, try to do it in a location where you don't normally hang out. He's probably going to develop some nasty emotional associations, whether he freaks out or not, so try to get them out of the way and leave them there.

If you want to comfort him for his loss, that's okay, but make sure to do it after he has recognized his loss. Otherwise you end up introducing ambiguity, and you know he has problems with that.
posted by LogicalDash at 8:32 AM on March 21, 2012 [1 favorite]

Can you try setting him up with some wonderful women? That way his romantic attention is deflected and you get to keep being a friend. Right now he may think you are his best option, so find someone better. Good luck.
posted by onlyconnect at 9:05 AM on March 21, 2012 [1 favorite]

I just don't want to hurt him!

This is basically impossible; even if you never explicitly reject him, unrequited feelings are painful too. It will be easier for you, however, if you do come out and explicitly reject him.

You don't need to tell him exactly why. Yeah, you certainly want to avoid telling him you think he's ugly. But you do need to be firm and not leave any wiggle room. "I'm sorry, but I am not attracted to you. It's never going to happen."

Be aware that the friendship is likely going to end no matter what you do. If you allow the current situation to continue, one of you will decide it's too unhealthy to continue. If you do explicitly reject him, he may be too heartbroken and embarrassed to have a close relationship with you.

It's not your fault you don't like him. It's not his fault he likes you. But that doesn't mean everything can just go back to normal.
posted by spaltavian at 9:08 AM on March 21, 2012 [1 favorite]

I have begun to feel like I'm taking advantage of him by being the recipient of his generosity.

I'd say you are. Not in a evil-hearted way, its just that you are allowing him to do stuff for you that he might not actually do if he did not have sexual interest in you. Back in the day, this was explicitly allowed, but now people are reconsidering.
posted by Ironmouth at 9:20 AM on March 21, 2012

"Friend, we're not going to date. It's just not going to happen. If it was going to happen, it would have happened already. And I have been very unfair to you by not being straightforward about that and letting you off the hook. I was trying to not hurt your feelings, I really did mean well, but that was wrong of me to let it drag on for so long.

"So it's not an option for us, but I will give you a tip for future endeavors with other women: that whole 'I don't want to know the answer!' thing has never, in the history of ever, gotten someone a good girlfriend. The answer already exists; be a person who wants to know things that exist. It will make you substantially more attractive to other people romantically, professionally, and personally."
posted by Lyn Never at 9:32 AM on March 21, 2012 [2 favorites]

OP, I was in your situation and it got really weird and awful fast. Cut it at the bud now. Say something like griphus said. Do not say that you're flattered. Do not try to explain why you are not attracted to him, he will either be insulted or start trying to convince you why you're wrong. Pull back a little bit after delivering the message. If he respects you he will not press the issue. If he continues to push, that is a giant red flag.

I'd say you are. Not in a evil-hearted way, its just that you are allowing him to do stuff for you that he might not actually do if he did not have sexual interest in you.

I don't think this is fair. She's genuinely interested in his friendship. She's not leading him on or indicating she reciprocates interest. If he is doing stuff because he wants to have sex with her, he is the one thinking he can get banging for doing favors.

However OP, you may want to cool it on accepting favors from him because they may be a method of him establishing control over you or dependence on him. I don't know your friend, but that's where my "friend" started going with his favors.
posted by schroedinger at 9:42 AM on March 21, 2012 [8 favorites]

All right, I’m here to defend the “I’m not attracted to you” line:

• It’s final. There’s no hope of improvement. It’s finished.
• He can’t argue with it. He can’t beg and plead to know the real reason and promise to change.
• It’s the truth.
• It’s something he already accepts- it won’t be earth-shattering to him if he already knows it on some level.
• Everyone can understand not being attracted to someone.
• Unattractive guys tend to hang their self-esteem on their niceness. You can argue with them until you’re blue in the face about how it’s a turn-off that they aren’t really listening or are secretly resentful, and cognitive dissonance will prevent that message from getting through. “I’m not attracted to you” may actually be less of a blow for a guy whose entire self-worth is tied up in being nice and friendly and helpful.
• It may actually preserve the friendship better.

I would suggest phrasing it like this: “I’m just not attracted to you that way.” Or “I’m just not attracted to you romantically.” Ever so slightly ambiguous, but gets the message across.
posted by quincunx at 9:55 AM on March 21, 2012 [6 favorites]

> I would suggest phrasing it like this: “I’m just not attracted to you that way.” Or “I’m just
> not attracted to you romantically.” Ever so slightly ambiguous, but gets the message across.

Why be ambiguous? Speaking as someone who has probably tried to "nice guy" his way into a few women's hearts, speak plainly.

"I'm not attracted to you and that's never going to change. I am interested in being friends and friends only. If you are interested in being friends with me, that's great. If you don't think we can be 'just friends' then we can no longer spend time together"
posted by dgeiser13 at 10:17 AM on March 21, 2012 [4 favorites]

It's not clear to me if you are not being clear or if he is being an ass - either way the answer is to say explicitly that you are not interested in dating him and do not get sucked into a discussion of why or if you might ever change your mind.

A true friend will repect your feelings (although he may not want to spend time with you.) I am sure you would have helped him out of jams so you don't "owe" anything.

Also, try not to get into several jams in a year. Independence makes dealing with issues like this much easier.
posted by Lesser Shrew at 10:33 AM on March 21, 2012 [2 favorites]

If you're looking to turn him down definitively without directly telling him you find him unattractive, you might resort to "chemistry." Who can argue with chemistry? Certain things react when thrown together in the beaker, other things don't even fizzle. So, when he brings it up, however tangentially and noncommittally, tell him you don't feel any chemistry, and that's not going to change.
posted by itstheclamsname at 10:39 AM on March 21, 2012

You have to tell him that it's never going to happen. I disagree with the people who say you should say exactly why: I think "I don't have any sexual chemistry toward you, and I am never going to have that with you; I am never going to be interested in anything other than a friendship with you, and that's the way it is" is an adequate answer, and stuff like "You're too thin for me and your hair is greasy and I don't like your receding chin and dandruff" is just mean.

Then it's up to him if he wants to be your friend--really your friend, not someone who's waiting to have a turn as your boyfriend and wants to keep his place in line by hanging around you.
posted by Sidhedevil at 10:47 AM on March 21, 2012 [1 favorite]

You grab the bandaid and you rip it off fast.

"I am not attracted to you. You and I are never going to date. Ever. I'm not going to come around. You're not going to convince me. Ever. I can't continue to be your friend as long as you fail to grasp this. I'm really sorry and I'll miss your companionship, but it really has to stop immediately. Your advances and insinuations are unwanted and make me uncomfortable. Let me know right now that you understand this."
posted by phoebus at 11:06 AM on March 21, 2012

You aren't doing him any favors by being nice. I would distance yourself/end the friendship. It sucks, but it would be better for both of you. He is never going to get over those feelings if he consistantly spends time with you.
posted by Silvertree at 11:30 AM on March 21, 2012

I have to say, while I absolutely don't believe that any level of generosity toward you -- ANY level -- entitles him to expect a better result when he makes romantic advances, I do believe it's the better part of valor not to accept certain kinds of generosity when you know someone is interested in you more than you are in them.

Under "certain kinds of generosity," I would place any significant outlay of money, any substantial inconvenience, and any significant entanglement with your personal life (for example, being the one you call during personal emergencies). That's not because it's manipulative or creepy of you to accept generosity, and it's not because it means you're taking advantage of him or intentionally giving him the wrong idea, and it's not because he's intentionally trying to buy you with favors. It's simply because it's safer to maintain a little bit of distance with people you know are in that position. He is in a vulnerable situation here, and I think you need to overcorrect in the direction of making sure he's not extending himself in ways that, as someone mentioned upthread, he would not if he truly understood it would never make you begin to see him as a romantic prospect. This isn't your responsibility to manage, but I think to keep it in mind is a kindness.
posted by Linda_Holmes at 12:30 PM on March 21, 2012 [8 favorites]

Oh god. I have one of these, and have had them before. Let me be the one to tell you that nothing that has been suggested currently is likely to work. How do I know? I've tried them all.

Let me ask a serious question: is this person really just unattractive to you? Or is he /actually unattractive/, in the kind of way where many other people are also going to have issues with this? Is his sensitivity coming from true, actual facts? If so, this guy may well not only have feelings for you, but he may see you as his only chance. This means that nothing you say, short of a straight up "You have no chance, ever, for many reasons which I am happy to elaborate if you make me" is going to work. It's like a drowning person.

This is not going to go away with nice solutions. Let me tell you how all of these solutions go. It goes like this.

"I really value having you as a platonic friend."
-Yeah, but how do you know we won't be great together? You should give it a shot. I love you and I will take good care of you and we already do XYZ together. What do you lose in giving it a shot?

"The chemistry just isn't there."
-Chemistry is hard to tell from friend-distance! You don't know-let's try going out sometime and see how it goes!

You need to let him know that you are not physically attracted to him.

My suggestion is to let him know directly, but if you really, really don't want his feelings, then I would suggest going through an intermediary. You're probably right, that directly hearing from you, "I think that you are not attractive to me" is really hurtful, but he may be able to withstand, "You're such a great guy! It's a shame she's not physically attracted to you at all."

Why? Because if you don't, he will never understand, and hang on, because he will see that you "click" in other, non-physical ways, and so think there is hope. There is no hope. This situation, and he, are likely to make everything awful for everyone ever. Seriously, believe me here. This does not get better with time.
posted by corb at 12:38 PM on March 21, 2012 [1 favorite]

The last time this came up it was during an online chat and he got really embarrassed and left the chat, in which he had said he wanted to talk to me about the possibility of dating but then a few lines later said he was feeling embarrassed and didn't want to know the answer.

There's no need for hints or subtlety; just be considerate. He was brave to to bring it up directly, and honest in saying he didn't want to know. Go ahead and talk with him. Thank him for being direct, and empathize about how awkward it must have felt. Maybe he "doesn't want to know," but for you, it's necessary that he understand that you consider him a friend and not someone to date. For most of us, it's quite rare that we meet someone we want to be with. You don't need a reason or an explanation, other than that you don't feel it. THere's no need to be apologetic.

He'll be disappointed and probably embarrassed. But the two of you are at a point where it needs to be said. And besides, he does already know your answer.
posted by wryly at 12:58 PM on March 21, 2012

-Chemistry is hard to tell from friend-distance! You don't know-let's try going out sometime and see how it goes!

"No. If I were ever going to have felt attracted to you, it would have happened already. I will never be attracted to you sexually or romantically, no matter how much I enjoy our friendship."
posted by Sidhedevil at 1:07 PM on March 21, 2012 [1 favorite]

I had this issue years ago and what I told my friend was that I loved him like a brother and anything more felt literally incestuous. It was the truth. We remained friends.
posted by St. Alia of the Bunnies at 1:31 PM on March 21, 2012 [1 favorite]

I also feel a little awkward, like he's been my friend for the last year because he's been waiting to have a shot at dating me. It makes me uncomfortable.

I see an undercurrent of manipulation here, this telling you about how sensitive he is to rejection, and the way that has clearly translated into guilt on your end at the prospect of turning him down. I think it's incredibly shady for a guy to cultivate a deep, intimate friendship with someone he has designs on without letting her know what she's getting into, and without taking ownership for his own feelings.

As much as he may be vulnerable right now, and as much as it may, technically be you who gives a response he becomes upset at, he is the one who is causing this situation to happen, if in fact he has been hiding his intentions from you for some time. He may be doing it because of ignorance or a lack of self-esteem, but it's still on his side of the line.

A lot of the suggestions upthread about how to turn him down are very good. I'm just saying that there may not be a response that results in him not being hurt, and that if he winds up still being hurt, it's his issue. I hope you recognize that you're always entitled to set boundaries with people, no matter how much they say it hurts them.
posted by alphanerd at 1:49 PM on March 21, 2012 [5 favorites]

I think it's incredibly shady for a guy to cultivate a deep, intimate friendship with someone he has designs on without letting her know what she's getting into, and without taking ownership for his own feelings.

I think that might be a little harsh. I'm not sure that being friends with the OP for a year, during which he's been open about his feelings to some degree, means he's somehow trying to manipulate. It sounds more like a situation where he became friends with her and then became romantically interested, rather than somehow cultivating an intimate friendship with her because he was trying to date her. At the very least, I think we don't have enough information to make him quite this, as you say, "shady." I think classifying him as having "designs" on her makes him seem calculating in a way that we don't actually know him to be. We don't know at all that the romantic feelings preceded the friendship rather than -- as is common -- followed from it.

Without more, I think he's just having trouble letting go of the hope that the OP might be or become interested romantically just as he has, and it doesn't sound like he's been told yet that that's not the case. So far, it sounds like it's been just "deflecting" or treating it as "flirting," which means his saying he wants to talk about the possibility -- even if he then lost his nerve -- is following a fairly reasonable path with someone he's gotten close to and is attracted to.

I don't think the issue here is that he's a manipulative jerk. I think she's quite frankly the one who needs to be sure to own her feelings, be straightforward about them, and if that means the friendship falls on hard times, then that's what it means. Not telling someone the truth because you don't want them to feel bad is often a close relative of not wanting to tell them because YOU don't want to feel bad, and unfortunately, sometimes you have to feel bad to be fair.
posted by Linda_Holmes at 2:11 PM on March 21, 2012 [1 favorite]

Do not offer to be his dating consultant for dating other girls. That advice is very well-meant, but can rub salt in the wound for him and also continue to involve you in anything involving him and his romantic life.

Don't be mean, but be final. I agree with some other posters--I'd say sorry, but this isn't going to happen, excuse myself, and put space between us for awhile. It's decisive and gives both people space to move on without wallowing in the awkwardness. That has worked for me before.
posted by anonnymoose at 2:47 PM on March 21, 2012 [1 favorite]

Don't deflect. Don't drop hints. Be blunt. The kindest thing you can do is to say you're not interested romantically and just want to be friends. Don't say "you're not physically attractive"; just say "I'm not interested in you that way."
posted by J. Wilson at 5:18 PM on March 21, 2012 [1 favorite]

To clarify where I was coming from, I'm looking at the OP's admitted discomfort with recent developments. The chat with him didn't just bring something new into the picture that they could deal with together, it caused the OP to reinterpret past events, past events where he talked about being more than friends, and the relationship that developed with him being motivated by these feelings.

In addition to that, he immediately changed the focus of the discussion to make it about HIS embarrassment, and the OP is now airing her feelings to us, instead of working them out with the friend, in part because of his rejection sensitivity.

So, when I look at this, I see a situation where this guy's found a way to air feelings which I believe he either knows, or should know, potentially stand to cause distress to the OP, while putting up barriers to honest discussion, either with plausible deniability of his seriousness, or with messages about rejection sensitivity or embarrassment at discussing a topic he brought up.

So when I talk about manipulation, and about shadiness, I'm not saying that this friend simply wants to get into the OP's pants, or that he doesn't want to be a good boyfriend.

What I mean is that the situation has been set up where only one of them is "allowed" to broach their feelings on this subject. That's the manipulation. The shadiness comes in where this person was cultivating intimacy with the OP with a goal in mind, which the OP may not have given him, had she known where he was coming from. That she now thinks he's been acting inauthentically for awhile.

Again, I'm going by the OP's stated discomfort about what she thinks his intentions were in this friendship all along. I'm betting that discomfort came from somewhere, from other things, too, besides what was stated in the post.

Where do I draw the line between one friend who simply has feelings for another and something "shady" or "manipulative?" I think it has to do with intimacy, a willingness not to probe subtly unless one is receptive to subtle rejection (meaning you can both recognize it and drop it if it happens), a commitment to bringing up feelings only if they can be discussed honestly and otherwise not bringing them up at all (which should be feasible if a friendship is good enough on its own terms), and most of all, a willingness to treat the other person's feelings as equal to one's own.
posted by alphanerd at 8:25 PM on March 21, 2012 [3 favorites]

a willingness to treat the other person's feelings as equal to one's own

I hear you, but she hasn't told him how she feels. Has not. Says so herself. Gently deflecting -- and even treating it like you would treat harmless flirting -- and that not being enough to make him not declare his feelings to her does not seem to me like the line between manipulative and not. It seems like the line between sharper and less sharp social skills. Same with "you can both recognize it and drop it if it happens." Not recognizing subtle rejection doesn't make you manipulative; that's really a harsh standard, I think.

As for the OP's reaction, she has a lot of reactions. She goes on and on and on about how great he is, and mentions once that it makes her feel like he only became friends with her because he wanted to date her. It's a huge jump to say "that has to have come from somewhere; thus, I assume that was his motive." That can also come from her, from her way of processing friendship and feelings. It has to come from somewhere, but that somewhere does not have to be being right about it. People speculate about other people's motives all the time, for all kinds of reasons.

As I read the facts, he didn't tell her, "I am terrified of rejection and really hate it when people reject me." She's interpreting, because they're close and he's her friend. I feel like the "he's a manipulator" theory relies on assuming that he's intentionally been subtly planting hints that he fears rejection so that she isn't, as you say, "allowed" to express her feelings. I don't think that's what she's saying. I think she's saying that because she knows him well and knows how traumatized he was by his divorce, she knows how he feels about being rejected.

I don't think she's doing anything wrong, but I don't think he's doing anything wrong, either. I think she needs to be okay with the discomfort it causes to say something hurtful to someone you care about, and she needs to tell him plainly that she isn't interested, and that his efforts to open a discussion about dating are making her uncomfortable. She's not guaranteed that he won't be upset, or that the friendship will continue as before. She's not entitled to have him sign off on her rejection or tell her it's okay. It's an awfully tall order to say, "He's too physically unattractive for me to date; how do I make sure that he's not hurt when I reject him on that basis?" She's entirely within her rights to reject him, but he's entirely within his rights to be hurt. It hurts when someone is "actively turned off" by your appearance; how can it not be? I find myself imagining if we were dealing with an OP who said, "I expressed to my dear friend that I wanted to date her, and she told me she thought I was wonderful, but she didn't like me 'that way,' and I know it's about my appearance, because she's told me a hundred times what a wonderful person I am. Now that we've had this discussion, she expects everything to stay the same between us, but I'm hurt by it, and now I'm uncomfortable, and even though I still care about her and I'm glad she was honest, I find myself needing some space, because the rejection still hurts." I think we'd understand.

I see the problem here as many others do: she's trying to be kind, but confusing short-term kindness ("I don't want to say anything that will make him upset") with long-term kindness. Long-term kindness absolutely sometimes requires short-term unkindness. It is her responsibility to tell him plainly how she feels, since she's the one who's uncomfortable. If she tells him, "I am not interested; I only want to be friends; let's leave it at that for good" and he won't stop, then you have a different issue. Right now, all you have is a guy who hasn't taken what she's convinced is an adequate hint. That may make him a guy who can't take a hint (though up until now, her hinting seems to be simply not paying any attention, which isn't really much of a hint). But I think it's unkind to conclude he's a guy who's trying to manipulate her or trying to disallow her feelings.
posted by Linda_Holmes at 6:06 AM on March 22, 2012 [3 favorites]

I just don't want to hurt him!

You are hurting him much worse by letting him hold on to a false hope. Tell him clearly and plainly, and however you frame the "no" part, include:

1. It's never going to happen.
2. I'm never going to change my mind.

By saying this you will be doing him the kindest favour you can, in your circumstance.
posted by ead at 8:43 AM on March 24, 2012

I've always said this line, "Aw, I'm flattered but I just want to be friends." That's it. Nothing more, nothing less.
posted by InterestedInKnowing at 6:15 AM on June 25, 2012