My friend is in love with another friend's sister?

DarlingBri has it. I think she needs to address it head on in an honest but gentle and kind manner. She needs to email (do NOT do it over the phone or in person, allow David the chance to be hit with this in private) him and let him down. Firmly, clearly, but not meanly. Griphus is right that any apologetic or wishy washy sentiment isn't going to help him, it is only going to confuse him. No "I wish I did but" or "You're a great guy but". Just clear, "No, I don't share your feelings." language. No matter what she says he is going to get upset, but that can't be changed. Having these obsessive love feelings for someone who will never return them is way more upsetting, so pushing him towards getting over it and healing. I would write something like, "David, I've been getting sense that you are having feelings for me that go beyond friendship and it has been making me increasingly uncomfortable. I feel that I really need to tell you that those feelings are not reciprocated and that they won't be. I know that I am being blunt and that this is probably upsetting for you to hear, but I don't want to risk leading you on or allow you to harbour hope that I will feel the same. I don't return your feelings and I know that this will not change. I am hoping that this message will help you to move on from your feeling for me so that you can redirect them to someone who will share them." Also, agreeing that this guy sounds like he has more going on than just awkwardness. His inability to pick up social cues points to his being on the autism spectrum, and he just doesn't sound well.

Thank you all for the responses. I have decided to suggest to the sister to use DarlingBri's script. All of your responses, in addition, have helped me realize that I still have much growing up to do and realizing that asking an online community for advice has both its benefits and disadvantages. Again, thank all of you!

Man, if any of you are over the age of 23 I'll be bowled over. Look, this is a very common situation among young geeks (and young people, period). Nobody wants to be the one to tell David to get lost or cut that shit out because of http://www.plausiblydeniable.com/opinion/gsf.html ruling your brains. And I'm guessing all the women involved are young enough that the world has not crushed the hope that creepazoids will just go away and leave them alone if they don't actively encourage them. First: none of you are obligated to hang out with David, no matter how much you feel sorry for him. If you can't bear to cut him loose and you simply must take him under your wing, then be good Social Skills Teachers and educate him. If you guys aren't giving him a heads up when he's being awkward and creepy then he's going to think his behavior is fine and dandy and he's going to keep carrying on with it. Yeah, it's not fun to confront people. But right now your passive-aggressive tolerance of him is making the situation worse. Second: it is time for the sister to ovary-up and practice the incredibly useful skill of firmly turning down an unwelcome suitor. This dude is not going to take a hint. Inventing a fake boyfriend is not going to deter him. Fake pictures are not going to deter him. These are all namby-pamby non-solutions people want to take to avoid a very necessary confrontation. This will not be the last creepy guy in this girl's life. The sooner she gets to be OK with telling guys to fuck off, the happier and safer she will be. Call the dude up and use DarlingBri's script.

David is behaving very unattractively. The first two rules are 1) be attractive and 2) don't be unattractive. David's friends need to make it clear to him how badly he is failing at #2. He's never even going to get to working on #3 if he doesn't fix that. If he hasn't even been able to talk to this girl, I don't think 'sister' has any obligation to do or say anything here. Unless he's getting in her face or scaring her - if that's the case he deserves a 'Back off, Creeper!'. No one is responsible for understanding David's feelings but David, especially if he isn't even making them known. Maybe a friend can take him aside and say that they asked 'sister' about David on the sly, and the response was that when they hang out, sometimes he is creepy and gross. Repeat that sometimes he does act creepy and gross. Make a commitment as his friend to help him not act so creepy and gross, especially around 'sister'. If David is truly incapable of reading social cues (and it's not just that no one has ever been a good enough friend to call him out for his behaviour)....I don't know, give his two best friends a bunch of red, yellow, and green cards? When he does something suave, give him a green card. When he pulls a creeper move, he gets a red card. If he gets a bunch of red cards in a row, maybe he should go home. If he starts behaving in such a way that one day 'sister' comes up and gives him a green card for doing whatever, you can be sure he'll want to do more of that.

I've been in a situation where someone had a very long-term crush on me, but continually tried to go through other friends to arrange something and never actually talked to me. It was incredibly awkward and hard to deal with, since I knew about the whole thing but didn't feel comfortable talking directly to the guy about it. I wish he would have just talked to me at some point - that conversation would not have been fun (I wasn't attracted to him) but it would have taken my friends out of the "messenger" position they were stuck in and given him a change to move on. If this situation has gotten to the point where the sister is fearful of the guy, then he has to be told bluntly that his behavior is inappropriate, no matter how sad it may make him. If she does plan to talk to him personally about this, it would be kind for you or her brother to be there so that she does not have to be alone with this guy in what could potentially be a volatile situation. I like ruthlessbunny's sentence: "This stuff is heartbreaking, but no one HAS to love you back, no matter how much you might want them to." Having a crush on someone DOES NOT mean they owe you ANYTHING (a lesson, might I add, that I had to learn myself during some intensely awkward high-school crushes). If she has made her own feelings clear, than further pursuit by this guy is verging on harassment and he needs to stop. It is not her job or your job to police this guy's feelings - being nice to him should not come before the sister's own feelings of safety.

I once went to party hosted by a good friend, which included our social group of the time, and (unusually) a group of her friends from college and before. One of these friends decided that night that I was fantastic. I got a phone call from my friend the next morning, making sure that I was aware of his interest and did not reciprocate, with a small amount of "and if you were interested in him we'd probably be talking you out of it because he is so not ready to date a girl", and then they went and sat down with him and explained to him that if he was expecting their help in getting together with me, he'd better think again because there would be no "coincidental group outings", none of them giving him my phone number, etc. because they genuinely did not think that we would be a good match. They may have even gone so far as to suggest that he work on a few of his particular social graces. All I know is, I dind't have to deal with him lurking around me, nor did I have to wait through that "I wish he would just ask me out already so that I could say No without looking presumptuous" period, nor did I have to have a confrontation with him at all. They understood the situation, and they took care of it. "David, I know you've been really upset over Diane, but she does not feel that way about you. You need to understand that you cannot ___, ___, ___ around her, and that the more you ___ the less comfortable she will be even going out as a group when you're around." He's been telling you how he feels (in writing, no less!) because he is hoping that you will help him. By doing nothing to discourage him, you are encouraging him, and doing the sister a huge disservice. He seems to attack you for monopolizing her time, to get you to be defensice, and say empty apologies and seemingly innocuous things like "Gosh, David, I'm sorry you're so upset, I had no idea you wanted to talk with her so badly", which he can then interpret as "and they'll be sure to incorporate me into the conversation next time". You need to explain to him that you will not be helping him, and why.

Cranberry Is David autistic? His "social awkwardness" and insensitivity to others' feelings suggest the possibility. Could his parents find treatment/programs for him? and Puppet Also, agreeing that this guy sounds like he has more going on than just awkwardness. His inability to pick up social cues points to his being on the autism spectrum, and he just doesn't sound well. It sounds to me like he has Asperger syndrome. (See http://en.wikipedia.org/wiki/Asperger_syndrome). This is a high-functioning form of autism. My cousin has it and acts very similarly toward women. He comes across as very creepy, even to me - as his cousin. My dad had to explain to him when I was younger to give me space and not be touchy. He would do things like play with my hair and such. He also isn't really allowed around my step-mother as he cannot stop staring at her chest and followed her around the house like a puppy dog even when she tried to avoid him. He is a 25ish year old adult. So when people have said he seems childish and teenager, it's probably because of this. Know that it's not his fault, but you need to set up boundaries. Having a Fake Boyfriend or something similar would make his obsession worse. People with social issues tend to cling onto all the information they can get. When I last talked to my cousin he complained that I didn't post on Facebook enough- creepy. (I have since blocked him from almost all posts.) I also think it's not your place to do much of anything. It seems you have been pushed into the middle. If he creeps her out, she needs to say something. It needs to be clear. If he does have Asperger syndrome then he won't get social cues like her avoiding him. I say they should keep their distance socially whenever possible, but be clear if she feels uncomfortable. Again, you may get pushed into the middle, at which point it may he useful to send a message along from the friend that he needs to back off, but again I suggest to support your friends, but stay out of it. If she (they as siblings) aren't willing to be clear with him, then it won't stick. It may not even stick if they are clear with him. Again, be support but you don't have to referee.

When I get back, John received a three paragraph letter from David saying how he was troubled that he couldn't talk to the girl because he was so awkward and didn't know what he could say...He said that he was in love with the sister and that he wants to know how she thought of him. I think John should tell David that either David needs to write a letter to the sister herself telling her this, or else he (John) can ask her how she feels and report back. (Which is really teenage, yes, but you guys are teenagers, right? Or nearly?) Whichever one David picks, the sister or John can then give him the unambiguous rejection he needs. I don't like pre-emptive rejection as a rule, not because it's too harsh but because it's REALLY difficult to do, much harder than saying no to a request for a date. Not just difficult as in awkward, but potentially messy and confusing too. I think the sister would feel cruel delivering it as strongly as she'd have to in order for it to be clear, plus I'm not sure if David, with his questionable hold on social appropriateness, would even get it. It's completely fine if she wants to do it, I'm just thinking when I was in college no one I knew would have had the maturity do it properly, especially to someone who behaved in a scary/creepy way. If she does want to do it, PuppetMcSockerson's script is quite good. And don't do the "fake boyfriend" thing. That won't stop him from liking her. Even people with great social skills and understanding don't automatically "stop liking" who they like as soon as that person starts dating someone else.

some suggested that she just reject him the next time they see each other so that this can be dealt with, but I feel that's too harsh. It's not "too harsh" to say, "You've been acting in a way that suggests you have feelings for me, and if that's the case I need to tell you that I'm not interested and your behavior makes me uncomfortable." He's acting in ways that make her uncomfortable and it's totally appropriate for her to tell him to back off. Yeah, it sucks to have a crush not reciprocate your feelings, but that's part of life. She doesn't owe it to him to tolerate his making her uncomfortable just to spare his feelings. You can help by doing the following: if she asks for advice on what to do, encourage her to set explicit boundaries with him. If she says she's scared of him and seems creepy, encourage her to trust her gut around him (i.e., don't make excuses for his creepy behavior). If you see him acting toward her or speaking about her in creepy or possessive ways, call him out on it ("David, when you say things like that, you sound like a creep.")