Quean Eye for the Straight Guy
February 18, 2009 2:07 PM   Subscribe

Is it acceptable to use somebody's feelings for you in order to 'respec' them so they can attract other women?

A guy who I take classes with recently made it very obvious that he has feelings for me. I don't feel anything for him in that way, but do consider him to be a friend enough to spend time with. Because of this, I'm being careful not to hurt his feelings, but will make sure that he 'gets the message'.

However, I feel like many (though not all) of the reasons why I don't find him attractive would make most women feel the same. I feel sad that though he's confident enough to try to engage with women, he doesn't stand much of a chance. I don't think he knows this though, and fear he's going to spend the next few years being rejected. Given he's 20, and that these should be the best years for dating and things, I feel I ought to do something.

Is it ever acceptable or welcome for a friend to step in and help in a situation like this? Especially knowing that their feelings for you would make it more likely that they would accept your suggestions? I wouldn't think of doing it too obviously, nor or saying explicitly 'do this and I'll date you'. I'm hopefully tactful enough to make him aware of things he could do, without him feeling pressed to do them.

So, has anybody experience of doing this/having this done to them? and was it welcome or just totally patronising? Also, I suppose, did it work, or just a total waste of time?
posted by Sova to Human Relations (43 answers total) 1 user marked this as a favorite
I would wait until he asks you for your opinion, if he ever does. And I would make sure that you're not stringing him along by hanging out with him. If he decides he doesn't want to hang out because his feelings are getting hurt, please respect that decision.

All this is from experience. Guy friend had feelings for me, I didn't reciprocate and told him so. We took a friendship hiatus for a while until it didn't bother him to be around me. He found a lovely girl and married her, without changing any of the things I would have suggested--he just needed to find the right girl. And we're all good friends now.
posted by peanut_mcgillicuty at 2:14 PM on February 18, 2009

It depends on what the advice it is to be. If he's schlubby and would just benefit from some new clothes and more frequent haircuts, hearing that doesn't hurt in the same way as hearing he's fat and has halitosis. It can even be done encouragingly - "You're not playing up your assets! You have a great physique, dress it up!" But if you don't have any constructive criticism, don't bother.

Definitely wait to help as a friend until you're mutually just that: friends. That means you have to tell him romance isn't going to happen and see if he still wants to hang out with you, first.
posted by Ambrosia Voyeur at 2:20 PM on February 18, 2009 [2 favorites]

Best answer: I'm concerned that any attempts to 'shape him' into a more desirable package might be perceived as sexual or romantic interest, regardless of how carefully you proceed. He may end up feeling manipulated.

Keep making sure he 'gets the message' about your lack of interest and stay friendly with him. If he continues to pursue other women and gets shut down repeatedly, he may well approach you for advice or questions. That's the time to help him out, when he's receptive - not when he's vulnerable.
posted by cranberrymonger at 2:21 PM on February 18, 2009 [6 favorites]

However, I feel like many (though not all) of the reasons why I don't find him attractive would make most women feel the same.

Right, because everybody is looking for the same thing.
posted by rhizome at 2:21 PM on February 18, 2009

Oh, and watch the movie, "The Shape Of Things."
posted by rhizome at 2:22 PM on February 18, 2009 [2 favorites]

Instead of trying to figure out how to help him with the things he doesn't know, you might want to work on the things you don't know. This part of your post tells us there are many:

"Given he's 20, and that these should be the best years for dating and things"

Ahh, the self-importance that comes with youth.
posted by 2oh1 at 2:29 PM on February 18, 2009 [1 favorite]

It's odd that you don't mention at all whatever it is you're talking about. I mean, what's the deal? Does he not work out? Does he have an annoying conversational tic? Does he lack gravitas? Is his wardrobe all yellow?

I guess maybe you were afraid of being recognized; or maybe you felt as though it just wasn't important to the topic. Either way, keep in mind that peanut_mcgillicuty is almost certainly right in this case: you aren't every woman, and you can't know what every woman wants.

I'm certain that below will follow a whole slew of comments saying this, but let me be the first to say: don't you dare. You have no idea what you're doing. It takes an extremely wise and perfect being to take another person and 'improve' them, and I think that the way you phrase this question indicates strongly that you are neither that being nor in a position to act as that being. You know yourself that you will probably just piss him off or hurt him; you're just not accepting yet that if you did that, it would be your fault for sticking your nose into his business.

Let me put it to you this way: his lot is probably to meet a great girl who ends up loving him deeply over time who can help him shed any unfortunate qualities that he manifests in a way that is gentle and respectful. If this doesn't happen, well, maybe his lot is to spend his twenties having a string of bad relationships that don't pan out, and to slowly rediscover his own self-confidence to such a degree that he can turn his pain into something stronger. But his lot almost certainly isn't to have a girl who he's interested in explain to him why he's just not attractive, not just to her, but to anyone. If he accepts that without being insulted, well, he's got other problems beyond whatever problems you have in mind.
posted by koeselitz at 2:30 PM on February 18, 2009 [3 favorites]

just totally patronising?

Um, yeah, that one. I know you mean well, but the message you end up sending if you try this is:

1) i am so great i would never ever date you
2) i am furthermore so great I know how you can fix yourself to attract other women
3) If you follow all of my fixing advice to the letter, you may become worthy of other women, but not me, of course.

If there's ONE thing, like he has really bad BO and doesn't know it, maybe figure out a nice way to tell him. But don't try to "make him over." Honestly, the best thing for his dating life right now would be to cut off all contact (even 'friend" contact) with you, his hopeless crush/crutch, and be around people who might reciprocate his interest.
posted by drjimmy11 at 2:36 PM on February 18, 2009 [6 favorites]

"It's so attractive when a guy does/wears/is [something]" will most likely be perceived as "I will date you if you do/wear/are [that thing]."
posted by Meg_Murry at 2:38 PM on February 18, 2009 [1 favorite]

You're projecting a lot of what you want on to this guy. You think you can make him more attractive to "most women". You think he should be dating more, you think he wants your help even though he hasn't hasn't asked for it in any way.

Please please please wait for him to ask or you'll just make things worse. And you have to be okay with the idea that he might never ask.
posted by Ookseer at 2:39 PM on February 18, 2009

It also occurs to me that you should consider this: if he's the type of youthful guy who inspires you to sigh and shake your head, just anticipating the pain he'll go through over the next few years (years that should be his best, no less!) if he doesn't shape up as you know he should; if your kindest heart balks at the thought of letting him walk into this trap (trap!) of attempting to attract women without knowing what he's in for and without knowing that he's woefully unprepared:

He's not going to be worth much as a friend to you unless what you value in friendship is the thrill of fixing broken machinery. My suggestion would be to find people who seem truly noble to you - people you look up to in such a degree as to be intimidated and thrilled by them at the same time - and spend time with them as much as possible. Please take it from me, as a matter of experience: 'fix-up' friendships are almost never really fulfilling in the way that friendships with really engaging and admirable people can be.
posted by koeselitz at 2:39 PM on February 18, 2009 [1 favorite]

Without knowing more it's hard to say. I don't know if these 'reasons' are just quirks in his personality (love 'em or leave 'em), or things he's deluded into thinking women like.

If he's a proud kind of person and hasn't brought this sort of thing up in conversation, then leave it be. If he's open to suggestions, he'll make it known. Guys can be pretty dense when it comes to this sort of thing though, being direct is the best approach if you choose to say something. Minor suggestions would probably be more helpful/doable than major ones -- 'girls like it when you look into their EYES when you talk to them, not their boobs' and such, rather than 'your sense of humor really sucks'. His sense of humor is probably a 'love it or leave it' quality I'm afraid.

If he's nice enough to be worthy of being your friend, and he actually makes an effort to 'swing for the fences' with girls, then don't worry, he'll find someone eventually.
posted by lizbunny at 2:40 PM on February 18, 2009

Also, major lollerskates at the idea that 20 is a great dating age for men. It's a great age for women, who have dozens of suitors and everything in their favor. Barring rock stars, pro athletes, and children of millionaires, most men get shot down on a regular basis until they're at least 25.
posted by drjimmy11 at 2:41 PM on February 18, 2009 [6 favorites]

Also, major lollerskates at the idea that 20 is a great dating age for men. It's a great age for women, who have dozens of suitors and everything in their favor.

Uh, no, it's not always that great for women either. Mid-30s was when dating really got awesome for me, mainly because I'd finally grown up and figured out who I really was and what I really wanted in life and in a partner. Seriously, just because our culture fetishizes youthful women of a certain type doesn't mean that being a youthful woman automatically equals having the world by a string.

Back on-topic: OP, please don't try to makeover your friend like this. It's potentially cruel and unlikely to end well, for plenty of reasons already enumerated. If he asks your specific opinion about a specific topic (e.g., "do you think these glasses I have are cool, or should I get new frames"), feel free to give a tactful but honest answer. Otherwise, zip it, kiddo.
posted by scody at 2:54 PM on February 18, 2009 [4 favorites]

I had help identifying ways I could improve my approach to life and living with the side effect of netting me better candidates for romance.

This was done by caring friends who asked me why I did certain things certain ways and then provided info on ideas for how I might get more successful results. Some of it was making changes to how I already did things, some of it was learning completely new stuff, and some of it was completely useless for me but ended up being useful for other people I met down the line.

If you were to take an approach along those lines without pity or condescension, you may be giving him the ability to avoid a lot of false starts and disappointments. There's still the chance he could take it poorly, but that's the risk you're running by even wondering about this.

Those who take the "wildlife documentary" approach to friendship will disagree with me heartily, I'm sure, but I believe part of friendship (and even just being human) is to get your hands dirty in helping other folks see their way through the bewildering maze of life.

What I wouldn't do, ever, is say anything along the lines of "I'm not interested in you that way, but here's how you can make others like you." That may be what you're doing at its most naked, but there's no reason to put that on it when it could just be about helping another person have a happier existence.
posted by batmonkey at 2:59 PM on February 18, 2009

No, no, no, no, no! ... it's up to him to figure this out, not there person he has pinned his affections on to tell him. It would be hard to imagine anything more hurtful in this situation than pointing out what you perceive to be his flaws. And when I say "perceive", I mean it, because his flaws are your perception. There's someone for everyone, he's just not for you. Be nice.
posted by lottie at 3:18 PM on February 18, 2009

Don't go there. Coming from you, it will be leading him on, and he WILL think you are interested in him no matter what you say.
posted by jenfullmoon at 3:18 PM on February 18, 2009

Response by poster: Ok, whoa. I thought I had tried to phrase my question kinda sensitively, like not reeling off his problems and such, but I obviously didn't, so let me. I'm not the perfect 'everywoman', but seriously, some of this is obvious, for example: he pretty much has a mullet hairstyle; he's probably not yet obese, but he's getting there; he talks like your dad; he thinks a 'cute' way to get a woman's attention is to stroke her hair; and his idea of chatting me up included: 'I rate you just below [my favourite actress]. How do you rate me?' (Those *exact* words.) I'm hardly worried about petty stuff, 'like this band, tell these jokes, wear dark blue denim not light blue'.

Also, I'm not going to say, 'you're ugly and weird and will never get a girlfriend, you better do something about your sorry self.' I actually like the guy personally, he's pretty kind and decent, so I don't want to hurt him, just gently give him some pointers. Seriously, do I have to cut him off for fear of hurting him over this, and just say 'tough shit'? I'm willing to do that, but as somebody said, I don't see friendships as a 'wildlife documentary'.

(Oh, and yes, I do think his twenties should be his best time for dating. I didn't know I was crazy for thinking that...)
posted by Sova at 3:23 PM on February 18, 2009

I feel sad that though he's confident enough to try to engage with women, he doesn't stand much of a chance.

How do you know? Are you a dating expert of some sort, able to speak for all women? You'd be surprised the people out there who "stand a chance".

This all sounds very patronizing to me. If I where him, and discovered your "plan" for me, I'd feel very patronized.
posted by ecorrocio at 3:53 PM on February 18, 2009

Your clarifications do not help your case. So he almost (but not quite) has a haircut you don't like, talks in a way you don't like, and is not obese, but might be in the future? Come on. The hair-stroking might be kinda creepy, but he's going to get told that by pretty much anyone he tries it on.

The problem here is that you are judgmental. And, yes, judgmental on the basis of insufficient experience and information, if your comments about dating in his 20s are anything to go on.
posted by game warden to the events rhino at 3:56 PM on February 18, 2009

I can't figure out why you just can't say "No thanks" nicely, and go about your life. Someone might like him just as he is. He might like him just like he is. If he hasn't asked, spare him the patronisation.
posted by lottie at 3:56 PM on February 18, 2009 [1 favorite]

However, I feel like many (though not all) of the reasons why I don't find him attractive would make most women feel the same.

Its impossible to know this. Its incredible how people of all types, including people you personally find repulsive, get dates. Perhaps you should act like an adult, give him the dignity he deserves, and tell him no instead of a laundry list of "change these superficial things for me and I'll consider it" teen comedy BS.
posted by damn dirty ape at 3:58 PM on February 18, 2009

Response by poster: Thanks everybody, I'll leave him be.
posted by Sova at 4:00 PM on February 18, 2009

Yeah, that's a very horrible pickup line.

I do think this guy could probably use some help. Okay: I'm sure that there are some girls who like weirdos, but for me and most of the girls I know, stroking my hair would just creep me out. But I don't see how you could help him without coming off as "if you do X/Y/Z I will date you" and that's really not what you want, especially if he's the sort of guy to mistake friendship for flirting.

(And seriously, people. It doesn't take a wise and perfect being to improve someone, just a concerned friend or mentor, or even a role model.)
posted by Xany at 4:03 PM on February 18, 2009 [1 favorite]

I sympathize with your impulse to help out, but I don't think it's likely to work the way you want it to. The biggest problem is that he is likely to hear "women will like you better if you do/don't do these things" as "I will like you better if you do/don't do these things." Particularly since he sounds somewhat socially tone-deaf, "fixing him up" is very likely to end up inadvertently leading him on however hard you try not to.

The other problem is that the behavioral issues you specify aren't easy fixes. "Get a better haircut" is straightforward enough. But "don't stroke women's hair without getting to know them a lot better" leads to much fuzzier questions like "so when IS it appropriate to initiate affectionate touching?"--the answers to which vary depending on the situation, the specific sort of touching, and of course the preferences of the woman involved. Likewise, "don't talk like someone's dad" and "learn more effective ways of chatting someone up" are much, much more complicated than they seem at first glance. If he had the social perceptiveness to improve these problems easily, he probably wouldn't have them in the first place.
posted by fermion at 4:07 PM on February 18, 2009

Ok, OP, I think people are being a tad harsh on you. I would definitely agree with Ambrosia Voyeur about waiting till you guys are just friends (namely, that he has gotten over his crush on you) before you mention anything. At this point it will be taken as, "If I fix my hair and lose some weight, she will date me". Which is not the message you want to send. Once you guys are on a mutually-agreed-upon friendship level, I think it's ok to gently hint at things like, "See that guy? I think that haircut would look good on you." If he strokes your hair, or someone else's, I think it's ok to pull him aside and tell him that that makes people uncomfortable. In other words, discreet, one-time observations. If he doesn't get the hint about his haircut, that's his deal. If he keeps on stroking hair, then that's his deal too.

Anything to do with is personality (ie, he talks like your dad - I'm not sure what that means, by the way) is best not mentioned unless he specifically asks you if you think the way he talks is keeping him from getting girls. Then by all means, discuss it with him.
posted by DrGirlfriend at 4:07 PM on February 18, 2009 [3 favorites]

Best answer: I've been in pretty much this situation, from a male perspective. My friend helped me out, took me clothes shopping, helped me pick a nice cologne, showed me how much to put on etc etc etc.

I found it generally helped my confidence a lot, and I had a feeling like I finally had an insight into what I was doing wrong, or what I could do to help improve the way I was putting myself out there.

The person who did this for me was previously an object of affection, and we'd developed a real and genuine friendship (which extends to this day) and I'm eternally grateful for what she did for me, it really helped me turn a corner and realise that a lot of things I had no idea about made a difference.

She did it with a sense of genuine care, and I didn't get the wrong idea - by that stage I just wanted to be friends with her as well. She also approached it gradually, I think she asked why I did the top button of my shirt up ... and it grew from there.

A lot of the comments above seem to be coming from a very judgemental perspective, and they are assuming you are as well. As long as you are coming from a place of genuinely trying to help, in a friendly way, then whats the harm?. Best case, you'll make a huge positive difference to his life. Worst case, he'll be a bit embarassed or just brush you off.
posted by Admira at 4:09 PM on February 18, 2009 [9 favorites]

If you like him as a person, befriend him. If you would only spend time with him to improve him, say you aren't avoid him.

If you're his friend, you could be blunt about some things and see how it goes. Don't let loose on all his character flaws. Don't mention "women might find you more appealing if x changed," just bring up the comparison and tell him it is still bothering you, and that no one wants to be the less hot version of some popular figure. And that stroking someone's hair is a very personal, usually intimate gesture, and not something to do to strangers. This is not grooming him into a more datable person, this is just trying to keep him from being socked by a protective (boy)friend.

I know guys that are shades of this. I think most people do. They're set in their ways, and you can't fathom someone becoming attracted to them. But suggestions should come from a friend, not a love-interest who only feels sorry for the guy.
posted by filthy light thief at 4:20 PM on February 18, 2009

Response by poster: Hey, thanks for those last few replies, they're the kinda helpful answers I think I needed.

I've been gentle about pushing him away from the idea of a relationship so far, mainly because I only found out the other day that he really likes me. I'll probably make it clearer to him once I have a chance. I shouldn't have to worry too much about hurting him with that, as I can point to myself as the reason (specifically my age: I'm seven years older, and I don't care if he was the best-looking 20-year-old in the world, it ain't happening).

I have to remain in contact with him because of class, but definitely will wait til it levels out as a friendship to see whether any help is wanted/welcome. I think that is best.

(Also, I still don't see the '20s best time for dating' as ridiculous. What's up with that? The average age at marriage for men in the US is 27, and I sure hope they aren't dating afterwards...)
posted by Sova at 4:25 PM on February 18, 2009


Maybe many Mefites don't remember themselves & others in their very early 20s, and earlier?

Being taken under a friends wing, and shown how do do x, look y, and get along in z social situation, is one of the most valuable things you can do/have done at that age, and is quite common - even from someyou you have an infatuation for.

Not to say it's necessarily a good idea from your perspective - the danger is in getting too involved, co dependent, and it may become hard to disentangle yourself, especially as you realise which things are actually how they like to be, rather than actions they are misguidedly taking in pursuit of their actual interests/goals.

God it sounds weird put like that, right? But it comes and goes in all social interactions - my ex-boyfriend learned the difference between leek/spring onion, lettuce/cabbage, and how he too could have variety & veges in his very own meals (not to mention which types of underwear were currently considered sexy by opposite sex contemporaries, and a bunch of other sartorial realities). I learned about the girly arts of makeup from goth guys and drag queens.
posted by Elysum at 4:42 PM on February 18, 2009 [2 favorites]

I still don't see the '20s best time for dating' as ridiculous. What's up with that?

I think that it's what seems to be your implicit assumption that dating after your 20s is either second-best or unusual. It's neither.

The average age at marriage for men in the US is 27, and I sure hope they aren't dating afterwards

That still leaves literally millions of men who aren't married at 27 (or who are married but eventually get divorced or are widowed). In other words, there's plenty of dating in the 30s and beyond that doesn't involve married men cheating on their wives. You seem to think it's some sort of race, which may be coloring your sense of "needing" to speak up to help fix your friend before he runs out of time. But really, he doesn't have a sell-by date stamped on him somewhere. Some people just take more time to come into their own.
posted by scody at 4:43 PM on February 18, 2009

Sova, I don't think anyone is ridiculing the idea that the 20s could be a great dating time so much as speaking in retrospect of their own 20s and later, and their relative dating experiences.

Sure, lots of people can and will have great dating/relationship experiences in their 20s, even their early 20s. however, many many people require more time to develop the confidence and abilities to put themselves out there and amass those great experiences. I know I did! I am 40. my best dating was definitely in the last 10-12 years!

even for those whose 20s are awesome, so many people I know had EVEN MORE FUN in their 30s, 40s....even 50s :D

also, any one have handy stats on divorce rates re age of marriage? just curious...
posted by supermedusa at 4:48 PM on February 18, 2009

On whups-I-shoulda-previewed:

Ah, exactly! I alsmost put "under an older friends wing", so so far, you're fitting exactly into my pictured scenario. Interesting.

Play up the fact that you are older, make it absolutely clear that you're not interested, but feel free to give him friendly advice on social situations, relating with his desired sex, and current fashion trends (there is a world of difference between telling someone they should dress/look like x, and informing them that "x is quite popular at the moment". I've known guys who were desperately convinced that dressing like an 80s mullethead would get them the girls they were interested in - note, they were not interested in the *style*, and were singlemindedly pursuing it under the misapprehension this would get them particular *girls*. Pointing out that those particular girls had an entirely different 'type' and that it looked significantly more... this decade (lets say 'foo'), was valuable. And they eventually chilled out enough to figure out what they actually liked...)
posted by Elysum at 4:52 PM on February 18, 2009

he thinks a 'cute' way to get a woman's attention is to stroke her hair; and his idea of chatting me up included: 'I rate you just below [my favourite actress]. How do you rate me?' (Those *exact* words.)

These are examples of inappropriate behavior, and I don't think you would be out of line to call them out. It's a far cry from that

"Look, you can't just come up to a girl and stroke her hair—it's creepy."

[to weird chat-up gambit] "Yeah, you can't do that, it's not really appropriate. OK, moving on, did you see Colbert the other night?"

I think Miss Manners would say that the correct response would be to say "I beg your pardon" and use the thousand-yard stare, but I think that would be even more humiliating and weird. If you say these things in the right way and move on quickly, you can hopefully get your point across without it being too embarrassing. And it would be helpful.

Hairstyle advice could be helpful, but you would need to do it tactfully.

Pointing out that he is overweight is a different matter. There is little chance he doesn't know he is overweight.
posted by grouse at 4:58 PM on February 18, 2009

"(Oh, and yes, I do think his twenties should be his best time for dating. I didn't know I was crazy for thinking that...)"

He's 20. Do you really believe he's so bad off that he'll lose an entire decade of dating?
posted by 2oh1 at 6:03 PM on February 18, 2009

I think if you are sensitive (and yes it helps you are that much older) you can pull this off.

But let me mention this: I have known this one particular single guy (about five or so years younger than me) for a few years now. It always amuses me that about half the women I know see him as totally ugly and icky and the other half have mad crushes on him and/or think he is totally hot (I know this because I am his friend and for some reason many of these women decide to confide in me.) So, the truth is that somewhere out there your little mullethead friend has a match, probably.

But if he will let you help him, go ahead. Couldn't hurt.
posted by St. Alia of the Bunnies at 6:25 PM on February 18, 2009

You're getting a hard time of it on here - keep in mind that if someone's offended by the very premise of your idea, they will likely continue to be offended no matter what kind of clarification you give.

I hope I'm not repeating what I said earlier.... but your friend sounds like a guy I know and that guy was tremendously insecure underneath all the peculiar, overbearing behaviour. Getting older and getting rejected from time to time helped him overcome a lot of his unappealing habits and develop realistic expectations of love interests without dulling the really interesting aspects of his personality.

In fact, once he became more confident, the collection of strange affectations were replaced by a genuinely cool and unique individual.... so it could happen to your friend too. Accept him as he is and he may feel more supported to grow/change of his own volition. And then you can take him shopping.
posted by cranberrymonger at 6:38 PM on February 18, 2009

I think the idea is good but you need to be careful about it since he is romantically interested in you. The best thing that happened to me RE: dating is that I found the online pickup/seduction community when I was 19; it didn't turn me into a misogynist or a player, but it did tell me that a lot of my behaviors were completely unattractive to women. It also showed me a lot of the things that attractive men think and do.

So, yes, I think it's important for him to know, and you should try to help him if you can do it respectfully and tactfully.
posted by PFL at 8:43 PM on February 18, 2009

As a guy who was long ago 20 and clueless with women (more via being shy, lacking confidence, not being good at the art of conversation than the things the friend in question is saying/doing) and didn't have an older brother, uncle, older nephew, etc., around who shared insights, observations... it did me darn well to end up with a (male) friend who was a few years older, a great source of suggestions with this boy-meets-girl stuff.

I woulda loved to have had insights from a female friend, too.
posted by ambient2 at 10:04 PM on February 18, 2009

Lady, go to WalMart.

Look the people.

Most of them are coupled. Despite being weird or obese or sporting mullets or completely bat shit insane (or all of the above.)

There is someone for everyone on this freakshow of a planet. =)
posted by JFitzpatrick at 10:30 PM on February 18, 2009

Once I was in your situation. I wanted to tell a friend why some people found him off-putting, but I knew it would be way too weird, especially since we weren't super close. Then we were both drunk at a party and he asked me, "why don't people like me?" Score! Having been waiting for months to tell him, I laid it out for him in as nice a way as possible, and afterward he really did make an effort to change his ways.

So, yeah. I would wait until it comes up. Just, if he makes a self-deprecating remark or talks about not being able to get a date, say "you know, if you ever want help with this stuff, just ask me." Just make sure you've thought of a nice way to say it.
posted by showbiz_liz at 10:35 PM on February 18, 2009

Also, major lollerskates at the idea that 20 is a great dating age for men. It's a great age for women, who have dozens of suitors and everything in their favor.

Ahahahahaha hell no. When I was 20 I was pretty miserable - none of the boys who were about lit my fire, and I ended up in a relationship that went on far longer than it should have, simply because I hadn't worked out who or what I wanted.

People change a lot during their twenties, and it may happen that OP is not the catalyst. I look back at some of the things I did, or wore, or said, and cringe. That said, I think he needs to be told that some of his behaviour is inappropriate. Don't phrase it so much as about dating - it sounds a bit like social skills altogether.
posted by mippy at 8:29 AM on February 19, 2009

People are being hard on the OP because she assumes that guy will want to be friends once she "gets around" to rejecting him. When I was 20, getting rejected was like a punch in the dick from an angry drugged-up chimpanzee, and nothing exacerbated it more than the chick telling me she wanted to be buddies. Now I would welcome both kind rejection and friendly advice, but I'd be really surprised if that was the case here. If you want to be his friend, OP, reject him sweetly and before he embarrasses himself, and then work on maintaining that friendship for a while. Then you can drop some tidbits of advice on him gradually. The chances are good though, that he'll want to avoid you once you break his heart into little pieces--respect that. It's pretty much the only defense a sensitive chubby mulleted pre-adult has in my...er...his playbook.
posted by Potomac Avenue at 9:49 AM on February 19, 2009

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