I have a friend whos a nice guy and has all of the nice guy problems.
He hangs out with me and our friends and is kinda like the little brother of the group.
Heres the problem, he can never get a girl. Like ever. When girls come to hang out with us theyre either sitting in everyones lap but his and stroking our ego. Hes also the shortest at 5'7 when we are all 6' and up.
How do I get him to be attractive to girls.
He used to be fat. Like 240lb at 5'7. I forced him to go to the gym with me and workout and after a year or two hes now 160lb. Now the catch is its still not enough to pull woman. Hes just not a fatass and still looks a little chubby but not FAT.
Then he gets his confidence broken all the time. He will setup to confess to a girl and then they mention they like taller guys, or more muscular guys. Or he'll invite a girl to hang out with us (I told him hed have more success if he combined them with the rest of his life) and they latch on to one of us. So he tries not to bring girls he likes around us. Which means we cant help him. Although we did force him to stop chasing 9.5/10s.
At first I just thought that women were at fault because they just use him as an emotional sponge and then date other guys. Hes the guy they look at and tell us we should be sweet like him, but they go for us and not him.
Now Im thinking however the problem is that he comes off as romantic but asexual if that makes sense. Like he doesnt want to fuck girls. Hes not bitter girls are fucking other guys, hes just salty he cant get a girl. I think woman pick up on that. Like when Im alone with a girl I can tease her into stripping but people treat him like a child who would be scarred at any sign of sexuality.
Is this the real problem with nice guys. That they are TOO nice and it removes any sexual tension that could possibly be created.
Pic related. The type of girl he likes (taller than him RIP)
the best you can do is keep pushing him at the gym. thats great progress and soon his body will catch up and he'll be lady-bait.
that being said, maybe try and talk to him directly about the way to pursue women., he seems to be a romantic, but girls dont like that til the relationship is already established. until then he should be more flirty and fun.
i think the best way to do it is to make a distinction between specific actions that make him more of an emotional friend and less of a potential partner.
Its not that hes too nice, which i'm sure hes a polite dude. But he doesnt have any self confidence and also yes, girls can pick up on saltiness and especially the desperation, which a lot of 'nice' guys try to hide with being nice in an effort to get into her pants.
He needs to first have other things in his life besides girls. Does he like to do sports or something? 5"7 is really not a problem. Being a bit chubby isnt that bad. But lack of self worth is. He gets used because he LETS himself get used.
>Like when Im alone with a girl I can tease her into stripping
That made me cringe. I'm just like your friend though. I think it's because I was raised by females and I was taught to think highly of them. I always need the female to make the first move with the flirting, otherwise I would feel like a sleazy asshole.
Nah I didnt go into the details, but he has bullshit nice guy mentality. Just assume hes a nice guy
>I just want everyone to be happy
>I just want to love and be loved
>Why cant I help people even though you say Im being a doormat
>girls can pick up on saltiness and especially the desperation
He only shows this when hes about to cry from never being loved. He also has a problem with guys using and abusing him as well. I find it disgusting how people try to blame nice guys like this. I disagree with trying to be so nice to people who dont deserve it but fuck you guys who try to say they have ulterior motives. Its part of the reason why I disagree with that. You only get shit for being nice.
He has self worth. And he doesnt ask shy or have a lack of confidence around others. Hell he tries for women more than we do. Its just imagine a girl rejecting you for something youre a little insecure about. He never even mentioned his height until the girl he liked rejected him for it.
>he seems to be a romantic
Yes, and I think hes too romantic and never builds sexual tension with women. Like they feel hed be offended if he saw a pair of boobs or something. Hes a little too respectful imo.
Why does it make you cringe?
He makes the first move. But its always a romantic type of move.
kek we did and hes started to. But you gotta remember women have guys falling over them.
I heard this is a common problem for people who lost a lot of weight. They are trying to fake confidence but in their mind they still see themselves as unattractive. In this particular case you describe that he comes off as romantic but asexual. I suspect that he unconsciously behaves in this asexual manner because he thinks that displaying signs of sexuality would make him offensive and creepy. You need to put yourself in his shoes. He's lived the majority of his life thinking that he's not allowed to display his sexuality out of fear of being mocked. The majority of people have enjoyed a life where they were rewarded at some point when displaying sexual attraction. These rewarding experiences is what encouraged them to persist in their sexually active behavior. He was conditioned to the opposite and therefore he naturally does the opposite. It's particularly painful in his situation since the male gender is typically burdened by social standards to make the first move.
Like with any issue, the first step to overcoming the problem is to be aware of it. Your friend needs to actively reminds himself that he can and should take the first step to tease a girl into stripping, when the conditions are right. He needs to be aware that he has associated a lot of negative feelings about sexual advances and that he needs to push himself through all this negativity. He needs to pay particular attention to body language and use it as proof for himself that a prospective partner is *not* disgusted by him and *does* want to sexually escalate the situation.
the other half is that there is nothing to build to romantically. if a girl already gets the boyfriend level attention without having to put out, why would they bother?
theres also the 'nice-slut' idea where girls are naturally not attracted to guys who are boyfriend-level-nice to lots of girls. they want to find a guy they can make be nice just to them.
but the innocence look probably doesnt help either
He believes in being a virgin until marriage. And that aura kinda comes off when hes in an awkward situation.
>should take the first step to tease a girl into stripping
he doesnt want a girl to strip for him. Hes the type of guy to never admit he wants to see a naked woman.
Like hes probably not asexual, but he doesnt want to display any form of sexuality.
When we first me I was also abstaining from sex but I still wanted to see a woman naked.
I guess his flirting has 0 sexual tension because of that.
Even if he believes in being a virgin until marriage he still needs to sexually seduce someone in order to be husband material. If he doesn't makes a sexual move then he is broadcasting himself as a friend. If he wants to be more than a platonic friend then he must broadcast his sexuality and incite a response. He doesn't need to actually put his penis in a vagina but he needs to make some measures of sexual comments and sexual teasing to prove that he is sexually compatible with a potential partner.
>Why are you taking such a huge interest in
Because hes around me for multiple hours everyday and when I hear someones problems Im the type to try and fix it instead of consoling them. Im very bad at consolation.
But part of me thinks hes a masochist for being nice to assholes.
I dont know but its annoying to her him say he finds girls 5'9 and up hot.
You should honestly assume that a women whos going to be taller than you in heels isnt attracted to you. Unless shes like 5'11
>He's lived the majority of his life thinking that he's not allowed to display his sexuality out of fear of being mocked. The majority of people have enjoyed a life where they were rewarded at some point when displaying sexual attraction. These rewarding experiences is what encouraged them to persist in their sexually active behavior. He was conditioned to the opposite and therefore he naturally does the opposite.
I wish I could tell you how deeply I relate to this.
I know at first glace this pickup artist crap seems like a scam, but what this guy talks about generally is just a good coaching technique when trying your luck in the dating world.
But if you're too lazy, essentially the best advice I can give is
>He needs to enthusiastically carry a conversation
>He needs to have cool hobbies, or have something interesting about himself that he's willing to talk about.
>He needs to accept that meeting random women is like applying to random jobs, if people don't have a reason or a reference to his character they probably won't do business with him. "Hot" girls like the pic you provided are especially anxious about trusting men because for the most part they do business with fuckboys on the daily and have trust issues because of it. You are way more likely to date someone like that if you're friends with them first. It's the simple truth.
>You have to accept that your physical attractiveness isn't really that important if you don't have a personality to compliment it.
>He has to also let these girls know he is interested in them. If he doesn't, then they won't put themselves in a position where they could SEE themselves with him
Good luck :3
Jokes that imply she should strip and or let me take her clothes off. Its really specific to the girl.
First thing any guy should do with a girl he likes is break the touch barrier immediately. Nothings worse than being afraid to touch the girl you like and she'll pick up on that. I suggest tickling her to do so.
Most recent girl I stripped was laying down and her dress was disgruntled so I jokingly pulled it up and said I was fixing it for her. She let me take it off under the ruse of fixing her dress.
tell him to read about the characterisitcs of a sociopath and aim to become that.
For those type of guys just trying to become sociopathic is the only way they can get any ''no fucks given'' attitude, telling him to just be confident won't cut it.
Total nice guy here, 22 year old kissless virgin. But I was never fat, I go to the gym for 5 years now and did basically anything I can to be the best physical version of myself
But even if I was a 10/10 supermodel I would probably still be a kissless virgin because I don't know how to sexually interact with women, or even general social interactions. There is no "mysterious,shy handsome guy" if the guy shows no interest at all. Girls approach me from time to time and I don't know how to show them that I am interested in them, the convo goes usually like this:
>hey whats your name im anonette didn't see you here before
>hey anonette, I am anon nice to meet you
>small silence pause
>so-o in what uni are you in
>oh at the blabla uni
>im at the blablabla uni
>bigger silence pause
>well, talk to you later
It's always like this, like I am in an interview for work. I don't know how to small talk about random shit to keep the convo going, it always ends with that awkward silence where normal conversations would go somewhere else but I don't know how to get there. And the sad thing is I am relieved when the conversation is over because I don't have to do those crazy conversation calculations in my head just to keep it all together
Don't know what this info explains about the OPs situation, but maybe it could give you perspective
This is not something you should aim to be. I doubt through any normal means you could realistically acquire said disorder. Imagine always being bored, the only time you find temporary relief is when you're feeding your addiction(s) or interacting with people in a manner that makes them do things that interest you, but may or may not be in their best interest.
Also there is the constant struggle with self control, but some don't even bother with that, that is typically how people end up in jail. It might seem all peaches and sunshine reading about them. Every interaction with people to some degree is fake.
ASPD is likely the pinnacle of a human's ability to indirectly destroy itself.
But thats not the point, he will never become an actual sociopath, but it might help him to stop caring so much about the validation of other people and go after the things he really want.
If you tell him to just be confident, he might end up making all kind of excuses to not do the things that he wants and will fall back to his old ways
Well in my experience, self improvement is typically down to a lot of incremental changes over time, rather than a sudden giant leap. Most 'nice guys' I've been around typically have low self worth and believe they aren't valuable enough to be around other people.
He would be better off trying to improve himself to the point that he sees value in his life. Fake confidence can and will get you laid, but rarely can it keep a woman of any value around.
Show emotional content motherfucker. I used to have the attitude that "oh nobody gives a shit how I feel about anything, so I don't need to bother with all of that." But the emotional content is what greases the wheels of a conversation. Let yourself show a real reaction to the girl.
If you're actually fairly emotionless (that's a real thing for sure), then learn to fake it. Either way, nobody cares about a totally dry small-talk conversation. Learn how to fake your way through the small talk, find some little piece of information from the other person that you can connect to something you actually do give a shit about, and go from there.
Don't be so terrified to be exposed. On the other hand, don't become a totally open book. I still struggle with all of this but I've managed to fuck a few girls and generally kiss a few more. Just think about it and put some effort. It's tough, but if you can get yourself out of that generally hopeless mindframe, you can find the motivation. Look out for your self, nigga.
From a guy who used to be exactly like him and is still a lot like him, I'm willing to bet the problem comes from him not getting experience with girls when the other guys his age were. He's not too nice, he's not even really lacking confidence, he just has no idea what the fuck he's doing, and no amount of coaching can get him through that.
Most kids start to explore their sexuality with other kids who are exploring their sexuality. There's no pressure to do things right because there's no expectation on what is right. For those of us that missed out on that for whatever reason, it's trying to play a game of catch up with a target moving at a much faster pace. We're still trying to find our footing while the girls are sprinting away, or at least that's what it feels like. It feels like there's no room for error and when you do fuck up you figure you're close enough to the start that you may as well walk back to the starting line and go home. The idea of being sexual with a woman starts to seem so foreign and you start to get so much anxiety about disappointing her that you start to believe that if a woman would just care romantically about you, she would forgive the sexual mistakes. With the goal of overt sexuality seeming unrealistic, you cling to a goal of innocent romance, the one that you never had, and just want to start there where it's comfortable.
Of course, none of this probably applies to him and I'm just projecting my own insecurities onto him, but whatever, I've got nothing better to do.
I've got to admit that I'm one of those fairly emotionless people. How do I learn to fake it?
I am coming at this from a complete lack of understanding from what you're getting at regarding showing "real reactions". Starting from the top of a conversation, what do I react to? How do we go from "hello" to having the sort of emotional connection you're talking about?
I am sorry, OP, but you cannot help him. This is not because he's beyond salvage; quite the opposite, he's doing almost everything right. Everything but one, but that one is a dealbreaker, and the last step is one he has to take alone. He has to face his fears and ASK HER OUT.
You said it yourself: he comes across as romantic but asexual. He doesn't show interest, and so women assume -quite reasonably, given the information at hand- that he isn't interested. If they knew the truth -that he wants them desperately, but doesn't make a move because he's too afraid that they might, horror of horrors, say no- they'd call him creepy, and they would be right. That level of rank cowardice IS creepy.
The most you can do for your friend is to tell him this, and urge him to get over his fear. You aren't in his head; you can't do it for him. No one can. This last step -and I assure you, it IS the last step- has to come from him.
1. Smile. If you're not used to doing that when you meet somebody new, it'll feel weird at first, and you might creep a few people out when you're still bad at it. You'll get used to it.
2. Demonstrate interest in the person. Even if you have to fake it. When somebody says hello, use a welcoming tone of voice and very open body language.
3. Demonstrate interest. Both in the other person, and in things that you like. The corrolary to this is listening to the other person's interest, sharing yours, and building common ground.
Since you're saying you're fairly emotionless, I would say either 1. you're suppressing your emotions or 2. you're really not interested in much about other people. I found myself mostly in the latter category, but that sort of fed into a general unwillingness to display emotions.
But that's the point: you need to figure that out, and the only way to do that is to try things. Think of it like a strategy, follow a game plan, and when you fail (because you absolutely will fail), take some notes (seriously, write down relevant notes about the interaction when you get home), re-evaluate your strategy, and try other solutions. Eventually it will start coming somewhat naturally, but you've gotta work to get there.
I hate when people say things like "just be yourself, just let the conversation flow naturally," because those things are both ingrained by habit. If you didn't build those habits growing up, you need to start. Except, it's harder now, because most people built those social habits when everyone around them was still doing so as well.
You can do it though, man. I definitely did. Let yourself be afraid, accept that you'll fuck up, give yourself permission to feel awkward (because EVERYBODY gets socially awkward multiple times a day), and then try. And don't expect perfection. With some effort, you'll become passable, and eventually you might start to enjoy it.
You've got this man. If I can do it, you can.
to add a bit: Study socially-savvy peoples' body language. Really study. Go home and take notes. You might look like a weirdo just watching people, but honestly you'll be no worse off than you are now, so just fucking do it.
I can't emphasize this enough: learn to observe what socially-successful people do. Practice integrating their social tactics into your own life. And DON'T try to emulate the awkward kids that you think you can relate to more, because they're fucking up too.
My final point: Once you start interacting with more people, once you start moving past the small talk into real conversation you'll notice something strange: you absolutely won't be interested in everybody you meet. You'll find that some people, or some types of people, who you had imagined you really wanted to get to know, just truly don't hold your interest at all. AND THAT IS TOTALLY FINE. You don't have to like everybody. It's just useful to be able to carry a conversation for a short period of time with more or less anybody.
Fuck, man, this is real advice. Thank you for this.
I'm going to try what you're saying. As far as being emotionless goes, I don't think I'm suppressing emotions, so I do feel like I'm in the latter category as well; but I _want_ to be interested in the stories other people have to tell. I just have difficulty starting those conversations and getting those stories flowing. I think I'm a little afraid that I'll go over the top and look _too_ interested in stuff. Is that what you mean by not being afraid to be exposed?
From what you're saying I guess I just need to try and that's how I'll learn, even if I fuck up. And I can do that.
Now let's break something down: You _want_ to be interested in other peoples' and interests. What I'm wagering, is that you're so focused on the idea of that social fantasy, that you're not paying attention to the actual PERSON who's in front of you. That causes you to 1) relate with the flesh and blood person in front of you and 2) as you said, fear putting somebody off. That's exactly what I meant when I mentioned fear of being exposed.
It's a balancing act, really. Let your interest come out, by all means. People love enthusiasm, particularly when it's regarding them. But then, relax about it to. It's JUST A PERSON, just like you. Nobody matters all that much, you know? Don't put other people on a pedestal.
And, it's cool man :D I feel really strongly about this. It's been a huge struggle for me and I've had very little advice, except for from one incredibly social friend who was a natural and didn't really analyze it much. Usually people who struggle socially aren't AT ALL receptive to advice. I'm glad you're open to it. You can do it man, if you keep the attitude you've got. Just BE OPEN MINDED. Let yourself go. You've got this. Good luck to you, brother.
Anywhere. You probably already have the reputation of being a weirdo, if you're kind of just there but don't talk to anybody. Some people on campus have absolutely said to each other "that kid doesn't talk to anybody."
Fuck it man. You won't be any worse off. And they're just PEOPLE. Their opinions are just as insignificant to your life as yours are to theirs. Fuck it, just start man. It's a journey.
>You need to put yourself in his shoes. He's lived the majority of his life thinking that he's not allowed to display his sexuality out of fear of being mocked. The majority of people have enjoyed a life where they were rewarded at some point when displaying sexual attraction. These rewarding experiences is what encouraged them to persist in their sexually active behavior. He was conditioned to the opposite and therefore he naturally does the opposite. It's particularly painful in his situation since the male gender is typically burdened by social standards to make the first move.
Holy shit you just described my fucking life.
goddamnit, when its typed all out like this you can really see the tremendous effort it takes just to get some puss.
And girls still wonder why guys that get laid alot get respected. This complete ignorance on their part is fucking frustrating
When i fake interest while talking to a girl, what should my ''goal'' be?
Do i have to come across as nice person? Do i have to make her horny?
Faking interest is hard when you don't even know WHY people like to talk in the first place.
Does it turn girls on when someone is interested in her?
you should stop letting himself hang out with girls that he wishes he could be with all day *cough* like you and your friends. you and all the rest of your mystical 6' tall girl club is a constant reminder to him of his insecurities. you're enabling his friend zoned behavior and as a result that's all he knows how to do. tell him to get some male friends so he doesn't seem like a fag and learn how to get confident. stop mommying him into a permafriendzoned loser.
No no no, that is not at all what I was trying to do. I was suggesting a method for a socially-awkward guy to teach himself how to socialize. Nobody owes you shit. Go fucking make something of yourself or die alone, you fucking pathetic idiot. Honestly the victim mentality with some people here is fucking pathetic.
Man, you described my problem perfectly. It feels like I am so far behind everybody else socially. Well, I AM really far behind everybody else socially. My social anxiety is a lot better than it used to be, but my social skills still suck ass from lack of experience.
Everybody says "Oh you didn't miss much. Teenage romance is awkward and dramatic and blah blah blah". Well, yeah that may be true but the point is that thats where everybody learns the basics!
At this point it almost feels too late, I fucked up by putting everything off. I'm 22 and I can't even talk to a girl I'm interested in without stuttering and blushing.
ur reading comprehention is really weak isn't it?
What victim complex are you talking about?
This post is just pointing out the sheer amound of mental capacity needed to understand the process of getting pussy, yet girls and some guys talk like its the easiest thing in the world and sometimes even judge you for it if you're not good at it. I have an easier time understanding advanced calculus and philosophy than this stuff.
1) He needs something to break his inhibitions. May I suggest pot or alcohol? And that doesn't mean over do it. That means 2-3 good puffs and 4 or 5 pints. Just to break down that quiet, shy barrier.
2) You need to get him sex with a slutty girl. Something where he isn't going to get emotionally attached and the girl isn't going to cling on to him. This will get him addicted to the scent and feel of pussy.
Before you know it hell be begging you guys to go to bars and parties to 'pick up'. Hes just got to break down that gate and get a taste...its like a bird leaving the nest.
That problem is so insignificant: stop parading bitches in front of your friend so he'll stop feeling so inferior and maybe focus on getting him a girl for a change.
>I don't understand why Chad feels so insecure with all these hot bitches on our laps while he sits in the corner sipping his drink.
Fuck off faget.
>implying I'm OP
>implying guy in OP is Chad
>implying women don't hate him because he's an ugly manlet who is self aware
>implying women aren't essentially the average man's gatekeeper to self validation that they have to get through to garnish self respect and social standing
>implying this site isn't full of people calling eachother virgins, manlets, betas ect.
It's his life, and his life is pretty insignificant so there's that.
Besides berating you, my point still stands if that's the case.
OP and OP's "squad" is causing their friend "that feel" by constantly showing him how fucking cool they are, without focusing on just him.
Great thread, maybe an asperger guy can help a little bit, because I dont describe the theory, but the practicing.
I dont have a lot of dating experience, sex with 5 girls one of those was a 2.5 years relationship, others where ONSs
Beeing interested in topics: A really hot 9/10 girl once was kind of hanging out with a 10/10 bro of mine, they talked about going skydiving, I asked, if I could tag along, not with the intention of catching her or impressing her, but because i really wanted to do that. We didnt talk much that evening, but when my bro was away, she came up to me and was joyfull, that we would both go skydiving for the first time together and how we would organise it and gave me her number. Went skydiving, got it on video, we texted a bit back and forth, but she initiated quite a few times and I was sure, she digs me. When we picked up our dvd with the video of the skydiving, it was hot, i was thirsty and said, I would go to mcdonalds for a drink and she joined me for a spontaneous date. That of course went miserably, because she shared no interests with my nerd ass and I never wrote her again.
On sexual tension: with some (insecure?) girls, not paying attention to them, but noticing and greeting their friends causes a lot of it.
- Night club, three slutty chicks, my bro once fucked one of them, so i greet them with my eyes, but dont say a thing, this goes on for weeks until one night, one of them stops me on the way back from the toilet and just kisses me (was my first kiss) and we basically kiss all evening and make out a bit, but at some point a friend wants to go home, so thats it.
1 of 2 wall of aspie text
part 2 of 2 wall of text
- Girl is a close friend of my female neighbor, dont know her really, but always greet my neighbor. One evening I small talk with my neighbor a bit and she stands there aswell and starts to ask me, if we should dance or go to the bar, ato all of which I decline, because a friend of mine was drunk as hell and I brought him home. made up my mind the next time i saw her, partied hard with her, fucked her (my first time) and left in the morning, before she woke up (here you might also see, that all of that happened with a common friend, that is part of the "connection advice" someone gave about, its important that a girl sees a connection with you, thats why having femal friends is a good start for those strugling with female contact)
I still need to learn more about building that sexual tension, will try more body language when possible.
As a nice guy that gave up on getting a women long ago my best advice is don't give a shit about the bitches witch most are. His best bet is to just find something he likes doing other than trying get some useless bag of problems and enjoy all the money he will have not being sucked up buy the useless bitches.
If he gets lucky doing this he will find a woman that likes what he likes doing and they might hookup. Don't be something you aren't i was a nice guy me friend was an asshole he got the woman i didn't but i finally found that it was cause he had drugs not cause they liked him they just wanted what he had witch is what 90% of them are they want your money your drugs your cock not you just something you have to fill the hole they have in there heart.
Yeah my bad, I misread that post. It did take me a fuckton of effort to teach myself how to effectively socialize. I'm still not great at it, but I can get by, and I've had some sex, met some people I've liked, and had a good time with it.
What I was railing about was the impossible attitude alot of people on here have. Making oneself out to be a victim is the best way to ensure that you continue to fail. And since the sjw people don't give a fuck about socially awkward nerdy white dudes, we're on our own. And that's how it should be, really. Work will set you free!!
I think part of that last part is that everyone gets socially awkward sometimes. So, when normies think about socially awkward people, they think about their own socially awkward moments, and fail to realize how fucking bad the problem is for some of is.
I think he may be trying too hard to get a girl, he sounds a lot like me when I was in my late teens early 20's. I would chat up girls, talk to them over social media, but then they would just start talking about the boys the actually liked and the things they hated about them. So I eventually "gave up" and started ignoring them and to my surprise they seemed more interested all of a sudden. It's kinda the desperation thing you were talking about, if you just ignore them they get frustrated because they feel like you should be fawning over them and your not.
I think this is also why a lot of guys claim they have more success attracting girls when they already have a gf. It's not because you're taken, it's because your not paying other girls attention because you already have one, and why people say you'll find a relationship when you're not looking for it.
i'm only 5'9" but all of my dude friends are around the same height so it doesn't make me look like the little brother as you mentioned.
that being said 160 at 5'7" is still pretty doughy, i'm two inches taller and i'm 135 (goin for dat dare ottermode that the small bitches love)
>Forces friend to go to the gym
>Insecure about another man's misfortune about interaction with the opposite sex
>Want him to continue breaking his ego down
>Doesn't let him chase girls he desires but they rather fuck you and your other dudebros
>b-b-but Im such a b-bro though
You're not a good fucking friend at all. In fact, you keep turning him into more of a pushover . The gym , asking out women, hanging out with you guys while he strokes your egos, that was all because of you. You don't even care about his insecurities. Obvious he's fucking miserable and has issues.
STOP FUCKING PRESSURING HIM FOR GOD'S SAKE
Listening is the key to getting and keeping a woman. The romance comes after he's had the girl's ass in the air screaming obscenities at each other. It's to make her feel valued even when logic dictates she should be ashamed. It comes down to the mind-set that you are gonna stab her with your cock; she damn sure ain't gonna stab herself.
What get girls is confidence and being a good entertainer.
Basically you need to make the interaction interesting and keep it under your control so they can just go with the flow. You can steer the situation the way you like and she will feel it's natural to go with it even if that means her panties jumping off.
It's simple. He needs to find a girl who is as nice as he is. I didn't find anyone who wanted to date me until I was 21, then I met this girl at college and we started going out. Only relationship either of us have been in and we're getting married in a couple of years.
See if you can help him get the rest of his life together. Once he's confident being single and being successful while being single, he'll end up being more attractive to women.