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A friend of mine is dating a woman I was into. Was it a shitty thing to do?

greenhawk

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Sorry for so much text, but I felt like keeping a lot of the details were important to the story. I appreciate everyone taking the time to read everything though.


A few nights ago I was out with some friends from work having a good time. At one point we were talking about 2 of the women who work at the apartments we live at. They both speak English quite well so we can easily talk to them. I find the younger one, Keiko, more attractive as she is my type and I have made some humorous comments about wanting to date her, but the other night started to talk about it in a more serious way since one friend that lives there said there shouldn't be any problem with Keiko dating people that live in the building as long as they don't get special treatment. So anyway shortly after that my other friend pulls me aside when I went to go get some more food and we weren't near everyone else. He tells me he is sorry to say this and he doesn't want to hurt me, but he has been dating Keiko. He said he didn't say anything before because he didn't realize dating her was actually something I was seriously thinking about until 10 minutes ago.

I told him I understood and thanked him for telling me. Of course I was upset and had to hold it in since we were at diner despite something like this has happened multiple times before in my life. I am into a woman and either someone I know ends up dating her or trying to date her while ignoring me or I find out she has a boyfriend after I started liking her and think of a plan to get to know her enough to ask her out. By the time I got back home I was able to let it all out. Despite all the crying, anger, pacing, and depression I felt I couldn't be mad at my friend. First of all he was the only friend to ever tell me he was dating a woman I liked because he felt I should know so that way I wouldn't find out later, he took me aside to make sure others wouldn't hear, and he asked if I was ok. Also while I did actually want to ask her out and would have wanted to date Keiko I never sounded that serious in front of my friends because 1. I was not sure if she could date tenants and 2. I don't have the game, looks, or skills to just ask a woman out just because I like her. If I was going to ask her out I felt I would need to know her for another 6 months at least. And to my friends credit he is taller then me, better looking then me, has more hair, and much better game.

I told my self I do not want to lose a friend over a woman, especially a woman who even if I dated her it could have turned out we had nothing in common in the long run or we might just not have been compatible in the first place. One could say he should have asked me first if I really was considering dating when I would make jokes about asking her out all the time, but then again you can also say because I never made it sound too serious it is my fault. I was able to work out today so I felt better for awhile, but then I did not get angry again like last night just upset and depressed about the situation. I know I can't do anything about the situation and being depressed about it isn't going to help either, but it was such a hard hitting moment that happened last night while having a good time. I think the thing that really is making me upset is that he isn't looking for anything serious yet I am. So if they keep dating he will most likely eventually break up with her and move on to someone else and I will be stuck wondering what could have been. If I also wasn't looking for anything serious then it would just have been a potential easy casual sex for 6-months to a year lost.

I have also learned some new information as of just yesterday too. My friend said she was interested in him as soon as he sent his passport photo to the office when he applied for an apartment. While in the office one day he said he mentioned needing to go to the immigration office and she said " oh I have never been there". With me she never did anything like that so one could conclude she would have never been attracted to me in the first place or even if she did go out with me she would have wanted to date my friend as soon as she saw him. Also my friend is 25 and said she is younger then him, I am 31 almost 32. Even if she was 24 that would make me 8 years older minimum and I don't know if I would be up for that big of an age different. I also want children sooner then later and she may want to wait a bit. Then there is the possibility of her not wanting to date someone that much older. My friend also mentioned how she somewhat moved in with him too and I know they are having sex and I saw her futon and some stuff of her over there today too. I have started to get more angry again and still feeling depressed and anxious too. I can't sleep and working out is the only thing that calms me down. Just today alone I spent 3 hours in the afternoon working out, mostly lifting weights, and then tonight spent another 2 and half hours at the gym again. My muscles hurt, my thighs are chaffed, but it felt so good to left keep lifting and when something like them having sex or out on a date pops into my head the rage just pushes me further and harder.

Of course after I am done working out the stress and anxiety come back. I am out on my balcony at 2 AM having anxiety over a hypothetical situation that never happened and never will happen. Even playing video games and reading comics isn't all that fun for me right now. Sleeping is hard to do as well and I am waking up an hour or 2 after going to bed. Like I mentioned earlier I have no right to be mad and yet this is really bothering me. I can even still hang out with my friend no problem. We still have fun hanging out together and there is no bad blood although I have yet to hang out with him when she is around.

So what does everyone think? Was that shitty of him to do or just a unfortunate series of events? Any advice, thoughts, or personal experience would be appreciated. Any advice for me? I am sure some of you have had something similar happen to you.
 
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Sorry to hear that. Sounds like the fear of rejection is prevalent in your life due to lack of self-esteem and it’s causing you plenty of anxiety. You’re showing typical anxiety symptoms now and you might want to focus on yourself instead of the relationship between these two. If you condition yourself you’re “incapable” or “less” from the very beginning, of course it’s hard to achieve much later on..

You’ve been rejected, it happens to the best of us. The harsh truth is two adults were attracted to each other and I don’t think they owe anyone an explanation. Your friend was kind enough to talk to you in a brotherly manner, but he didn’t have to.
 
Oh, boy ... I’ve known that feeling.
One of my best mates — handsome fellow, comes from a wealthy family, whip-smart, an art enthusiast and a really nice guy — did that to me three times.
I was simply getting along in my first job, fresh out of university, while he was on the fast track to a senior role at his first employer. He was a good role model for someone like me.
Then we both fell for this lovely and athletic lady, who worked at a big ad agency. We met her at a party. I knew from the way she looked at him and danced with him that I had no chance.
Fortunately, she was renting a flat with three other colleagues. So I thought maybe I’d get lucky with one of her friends. I did, eventually, after our second double-date with our mutual friends.
Later, I moved to another job that sent me overseas. That didn’t go well in the relationship department, so I broke up with my girl.
Months later, my friend visited me and he brought along my ex, who became his new girl after breaking up with the original centre of our affection at that party a long time ago. No worries, I said, since I brought along a pretty new colleague when we met for dinner.
Several months later, my mate took a job in the same city where I was working. I was on holiday with family when he moved, so my colleague-turned-GF showed him around town.
You already know where this is heading: they hooked up. So when I returned I had no girl and I lost a good buddy.
I simply moved on. Life is too short to dwell on those things.
So it’s good that gym work is somehow helping you cope. Continue and go prosper. There’s plenty of fish in the sea.
Thank you, too, for making me reminisce about something that happened decades ago. Lessons learned.
Cheers!
 
I understand you are seriously asking this question but I don't really understand how your friend could have been more of a friend to you. Do you expect him not to date every girl you have ever met?

You were just too late. Get over it.

And as you know nothing about this girl stop imagining your future with her. As much as we all know she might be a total maguro in bed and wants to use the bed only for eating cookies which she makes you bring to her from L'épi D'or which is 23 minutes walk away and it's raining. Every day.
 
Sorry to hear that. Sounds like the fear of rejection is prevalent in your life due to lack of self-esteem and it’s causing you plenty of anxiety.

Rejection is common in my life when it comes to women, it happens about 97% of the time, but rejection has never made me feel this way. I got over my fear of rejection quickly after it kept happening again and again. When a woman would reject me I would be disappointed, but just laugh it off because I expected it. I feel like this is happening because I was not rejected. I was never given the "No" to prove my point. The potential relationship was never stamped out, but rather remains in limbo. Something similar happened last year. There was a woman I was into and had known for 11 months and was waiting for the right time to ask her out. We got along great, she spoke good English, she was a few years younger then me, we like some of the same hobbies, loved kids, and she came from a close family. However on my Birthday of all days too I found out not only was she married, but also pregnant. To make matters worse she came to the school the night to get something so I had to see her. I had to see her again a few more times before I changed jobs and it made me feel like this too, but not as extreme. In that situation it was more or less the same thing. I wanted to date her, she never mentioned a boyfriend or husband when I asked her what she did on holidays, and her facebook and instagram never mentioned a boyfriend or husband. With her I also never got the rejection, was never told the "No" and scenarios like that hurt way more.


If you condition yourself you’re “incapable” or “less” from the very beginning, of course it’s hard to achieve much later on..

I don't look at it as "incapable" or "less" I look at it as being realistic of who you are and your tier in life. For example back when I was an assistant teacher living with my dad there was no way I was going to get a teacher who lived on her own to date me.


. The harsh truth is two adults were attracted to each other and I don’t think they owe anyone an explanation. Your friend was kind enough to talk to you in a brotherly manner, but he didn’t have to.

You are absolutely 100% right. Thank you for reading everything and giving your advice.
 
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Rejection is common in my life when it comes to women, it happens about 97% of the time

To me that sounds like a great success rate. I estimate mine to be around 1% which I like too. It means I only have to talk to 100 girls before one of them jumps in to the bed with me.

The thing though is I like talking to girls. So it's a win-win for me. And win for those 99 girls, and a lose to just one of them. :p

I don't look at it as "incapable" or "less" I look at it as being realistic of who you are and your tier in life. For example back when I was an assistant teacher living with my dad there was no way I was going to get a teacher who lived on her own to date me.

That's right, you cannot get the girls because you are giving up before trying. You are way too serious about the whole thing. If an old, fat, ugly, perverted guy with a sick sense of humour like me can get a girl to be alone in a locked room with him then anyone can.

In baseball they say nobody bats thousand so just take the misses as normal. And if you squeeze the bat so hard you cannot even swing then you'll be hitting no balls either. Relax your shoulders, keep you eye on the ball and swing at every pitch that is thrown at you.
 
Oh, boy ... I’ve known that feeling.
One of my best mates — handsome fellow, comes from a wealthy family, whip-smart, an art enthusiast and a really nice guy — did that to me three times.
I was simply getting along in my first job, fresh out of university, while he was on the fast track to a senior role at his first employer. He was a good role model for someone like me.
Then we both fell for this lovely and athletic lady, who worked at a big ad agency. We met her at a party. I knew from the way she looked at him and danced with him that I had no chance.
Fortunately, she was renting a flat with three other colleagues. So I thought maybe I’d get lucky with one of her friends. I did, eventually, after our second double-date with our mutual friends.
Later, I moved to another job that sent me overseas. That didn’t go well in the relationship department, so I broke up with my girl.
Months later, my friend visited me and he brought along my ex, who became his new girl after breaking up with the original centre of our affection at that party a long time ago. No worries, I said, since I brought along a pretty new colleague when we met for dinner.
Several months later, my mate took a job in the same city where I was working. I was on holiday with family when he moved, so my colleague-turned-GF showed him around town.
You already know where this is heading: they hooked up. So when I returned I had no girl and I lost a good buddy.
I simply moved on. Life is too short to dwell on those things.
So it’s good that gym work is somehow helping you cope. Continue and go prosper. There’s plenty of fish in the sea.
Thank you, too, for making me reminisce about something that happened decades ago. Lessons learned.
Cheers!


Thanks for sharing! That is fucked up man and 3 times to. The 3rd example is the most fucked up since he flat out went for her while she was still your girlfriend. At least she was just a girlfriend and not a wife. It sucks when 2 guys ruin a friendship over a woman, but I feel like your friend would have kept doing that. A year before coming to Japan there was this woman I liked and wanted to ask out who I would see sometimes when my friend had a party. He was able to sense I was into her and one time even told me she was going out to dinner and see a movie with everyone so I should come. During dinner I was talking to her a lot and being a bit flirtatious and my friend was nodding at me saying "good job man keep it up". I didn't see her too much after that and then I noticed my friend was hanging out with her more in group pictures he posted and it was obvious he wanted to date her. One night I just asked him if he was trying to date her and he said "there is a 50% chance I am thinking about asking her out". He also had a girlfriend at the time too, one he had been dating for 7 years. I wasn't mad because at that point I was over her and realized the relationship wouldn't have gone anywhere.

How did you cope though? How long did it bother you each time?
 
I understand you are seriously asking this question but I don't really understand how your friend could have been more of a friend to you. Do you expect him not to date every girl you have ever met?

You were just too late. Get over it.

To me it was just more something that came out of left field. I thought the comments I made about dating Keiko would suffice as me being into her and he would stay away as that is what I would do, but I shouldn't have thought like that. You are right, I was too late. I needed more time to be able to ask her out and he didn't.


And as you know nothing about this girl stop imagining your future with her. As much as we all know she might be a total maguro in bed and wants to use the bed only for eating cookies which she makes you bring to her from L'épi D'or which is 23 minutes walk away and it's raining. Every day.

Yup and that is one of the reasons why I don't understand why I am so upset. I only know her from seeing her in the office. She could have been a maguro like you said, eat food in the futon, she could have told me to stop buying too many video games and comics, could have been a huge bitch, could have required I ask her permission to hang out with friends, or perhaps we wouldn't just be compatible due to age different, stages in life, or just personality. I have been telling my self that the past few days too. Maybe it is because this potential relationship felt very possible since out of all the women I am interested in or have been interested in I see her the most often. Speaking of other women there are 3 other women I am into as well so that is another reason why I don't get why I am so upset. Those other 3 I only see once a week though so asking them out will be harder, but still I have 3 potential choices although if I ask the wrong one out I think I will lose a shot at the other 2 lol.


To me that sounds like a great success rate. I estimate mine to be around 1% which I like too. It means I only have to talk to 100 girls before one of them jumps in to the bed with me.

The thing though is I like talking to girls. So it's a win-win for me. And win for those 99 girls, and a lose to just one of them. :p

2% of that were girlfriends and I didn't earn then. My first girlfriend I met because my friends younger brother went on a date with her and she didn't like him so he gave me her number and told me to text this person and we ended up talking back and forth because we had the same major. That Tuesday we met at school and that Thursday I was her boyfriend. My second girlfriend I met because my first girlfriend introduced us and in less then a week she said I was her boyfriend. Also I am not into random hook ups with women. I know that is highly hypocritical because I see escorts and it is, I have my reasons, but for me it is either have sex with a girlfriend or escort. No random hook ups. So even if I had the ability to flirt with a woman and make her want to sleep with me right away I wouldn't do it.


That's right, you cannot get the girls because you are giving up before trying. You are way too serious about the whole thing. If an old, fat, ugly, perverted guy with a sick sense of humour like me can get a girl to be alone in a locked room with him then anyone can.

.

Do you have money, height, status, or that typical gaijin look though? I sure those all play a part.
 
Ummmmm... wow.

The problem here is not your friend. The problem is your social anxiety. You mention thinking that you need six months to be comfortable enough to ask a woman out... if a friend of mine mentioned a woman was cute and did nothing about it for months on end, I’d assume he wasn’t interested and she was fair game, just like your friend did.

Have you considered talking to a counsellor or therapist? A lot of people are hesitant, but they’re often incredibly helpful, especially for things like this.
 
How did you cope though? How long did it bother you each time?

A good night’s sleep was all it took.
I was so much younger back then, had the energy of a wild stallion, took good care of myself and had a strong sense of karma.
It would be nearly another decade when I really fell so hard for someone and got my confidence shaken when things went south.
But all these things pass, bro.
I repeat: Life is too short. Best to move on.
 
2% of that were girlfriends and I didn't earn then.

Dude, there is no "earning" a girl. She either thinks you are interesting and wants to know more or not. You don't have to go through a series of challenges to be awarded her eternal love like in some ancient mythologies.

Do you have money, height, status, or that typical gaijin look though? I sure those all play a part.

Look what you are doing here? You are making up excuses why you will fail. Continue to do that and fail you will.

I make no money, my status is unemployed and moreover my state of mind is unemployable know-it-all fuckwit, and if by typical gaijin look you mean those nerdy looking guys who wander around in Akihabara wide-eyed and drooling to their "I love anime" t-shirts when seeing anything with a pair of boobs then I have nailed that look perfectly.

And none of that matters. Just talk to the girls you think are interested in. How else they, or anyone else for that matter, are supposed to know you are interested in them? Or if you can't then do as @Sudsy recommended and talk to a therapist. Something like that might be able to kick you out of your own head and to this world all the girls are living in.
 
Of course I was upset and had to hold it in since we were at diner despite something like this has happened multiple times before in my life. I am into a woman and either someone I know ends up dating her or trying to date her while ignoring me or I find out she has a boyfriend after I started liking her and think of a plan to get to know her enough to ask her out.

You were a pussy. You stalled because you lacked the balls to make a move. You missed your shot. Sorry. You've done it before, you'll do it again.


By the time I got back home I was able to let it all out. Despite all the crying, anger, pacing, and depression I felt I couldn't be mad at my friend.

I'm going to be very blunt because you need to hear this and you do seem genuinely nice (to a degree) and I hope your luck will change: You sound like a weak, whiny fucking bitch, and that's probably why you live a life of repeated cockblocks.

When a normal guy seeks a hot girl he thinks, "FUCKING EH, I'M GONNA GO ASK HER OUT!" And then he pounds four of five beers, staggers over and gives it a go. Shut down? Fuck it, do it again thirty minutes later with a different girl. You see a girl you like and your immediate thoughts are: OH NO, AM I TOO FAT? AM I TOO UGLY? AM I TOO BALD? AM I TOO POOR? MAYBE I'M A CLOSET FAG AND JUST LIKE HER SHOES? Then you wring your hands for an hour, all the while droning on to anyone nearby about your feelings, and your fears and your insecurities, and when you look up one of the normal guys has already bought her a second round of chu-hais and practically has her panties down.

There is a defined group of males who make educated arguments that females are drawn toward men who are sensitive, and in-touch with their emotions and inner-beauty, and who love to express their feelings; these men are called PUSSIES, and are usually virgins who will die lonely (or married to a grotesque thing 30lbs heavier and 40 years older than them). You need to knock that shit off NOW.

I don't give a shit what your friends from the high school chess club told you. Women don't want a whining, insecure pussy who bleats on about his feelings and cries like a fucking adolescent girl. What can you do? Marlon Brando put it well: "YOU CAN ACT LIKE A MAN."

First, you say that when you're attracted to a female, you worry you aren't good enough. This is easy. YOU PROBABLY AREN'T. So lower your expectations.

Next, ACT LIKE A MAN. Go to a large party, gathering or gaijin bar. See any girls you think are attractive? Found one? Nope, you're probably too fucking ugly. Lower expectations, remember? So now try to pick out one you think inhabits roughly the same level of unattractiveness that you do. Preferably a lonely looking one with prettier friends. Found her? Good, now pound a few drinks and walk over and start talking. You do NOT talk about yourself, do NOT talk about your feelings, do NOT whine about anything. For once in your life, ask her about HER and stick with that conversation as long as possible because you already know you have a habit of focusing on yourself.

If you can manage to successfully man-the-fuck-up and get her into bed, then congrats...you've now established a baseline. You can score with a girl "that" ugly. Now, you work your way up. Keep trying it out with a girl just slightly prettier, until you've hit a level of attractiveness where you keep getting shut down. Then you know your limits.

I've just solved your life for you. Next, I run for President.
 
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I had to stop reading at the point where the OP said he was crying. I was eating a grilled cheese sandwich and I started to gag. Then I scrolled down to the point where Keihan called the OP a pussy. I am 100% confident that everything written in between where I stopped and where I started again is inane and meaningless drivel so I don’t need to read it. And Keihan is correct. Message to OP, don’t be a pussy. Women are, as Mikey said, like maguro. (I did read his entry.) Which means, until you sink the gaff into it and drag it over the transom into the cockpit, you haven’t caught it and it’s not yours. And as some other idiot even stupider that Mikey once said, there are plenty of other fucking fish in the sea.
 
I'm a little drunker now and had the chance to peruse the rest of OP's posts, and I think I've been able to put together a profile (again, I'm drunk). OP is an overweight and generally unattractive guy with severe confidence issues, a pronounced tendency to overthink things related to relationships, has probably never had an actual meaningful romantic relationship before and probably suffers from a pretty standard case of obsessive-compulsive-disorder. He has a tendency to create vivid, hypothetical romantic fantasies in his mind as he obsesses over certain females, all the while hating himself for being too [insert negative here] as an excuse for why he hasn't yet asked the girl out yet "but plans to." He probably stays up late at night acting out different roles and hypothetical situations, trying to build up his confidence, and spends enough time doing this that when he gets "rejected" (i.e., a normal guy asked her out and they're humping now) he feels even more dejected.

OP, you wanna know what works WONDERS for guys like you? Honestly? COCAINE. Obviously, I'm not suggesting you break any laws or anything along those lines, but I've seen a few shots of Chivas Regal and a couple of lines turn socially-backwards loser chumps into self-professed Don Juans....if only for thirty minutes at a time. But you come correct with a couple of bumps and I guarantee some lonely, chubby tag-along at the bar will definitely bob your knob in the parking lot after a few rounds. Get to work!
 
I'm a little drunker now and had the chance to peruse the rest of OP's posts, and I think I've been able to put together a profile (again, I'm drunk). OP is an overweight and generally unattractive guy with severe confidence issues, a pronounced tendency to overthink things related to relationships, has probably never had an actual meaningful romantic relationship before and probably suffers from a pretty standard case of obsessive-compulsive-disorder. He has a tendency to create vivid, hypothetical romantic fantasies in his mind as he obsesses over certain females, all the while hating himself for being too [insert negative here] as an excuse for why he hasn't yet asked the girl out yet "but plans to." He probably stays up late at night acting out different roles and hypothetical situations, trying to build up his confidence, and spends enough time doing this that when he gets "rejected" (i.e., a normal guy asked her out and they're humping now) he feels even more dejected.

OP, you wanna know what works WONDERS for guys like you? Honestly? COCAINE. Obviously, I'm not suggesting you break any laws or anything along those lines, but I've seen a few shots of Chivas Regal and a couple of lines turn socially-backwards loser chumps into self-professed Don Juans....if only for thirty minutes at a time. But you come correct with a couple of bumps and I guarantee some lonely, chubby tag-along at the bar will definitely bob your knob in the parking lot after a few rounds. Get to work!
Yea cocaine or Prozac or its modern day equivalent. Or we could all pitch in a 1,000 yen and have Yuriko give him a confidence building blowjob as her swan song.
 
You were a pussy. You stalled because you lacked the balls to make a move. You missed your shot. Sorry. You've done it before, you'll do it again.




I'm going to be very blunt because you need to hear this and you do seem genuinely nice (to a degree) and I hope your luck will change: You sound like a weak, whiny fucking bitch, and that's probably why you live a life of repeated cockblocks.

When a normal guy seeks a hot girl he thinks, "FUCKING EH, I'M GONNA GO ASK HER OUT!" And then he pounds four of five beers, staggers over and gives it a go. Shut down? Fuck it, do it again thirty minutes later with a different girl. You see a girl you like and your immediate thoughts are: OH NO, AM I TOO FAT? AM I TOO UGLY? AM I TOO BALD? AM I TOO POOR? MAYBE I'M A CLOSET FAG AND JUST LIKE HER SHOES? Then you wring your hands for an hour, all the while droning on to anyone nearby about your feelings, and your fears and your insecurities, and when you look up one of the normal guys has already bought her a second round of chu-hais and practically has her panties down.

There is a defined group of males who make educated arguments that females are drawn toward men who are sensitive, and in-touch with their emotions and inner-beauty, and who love to express their feelings; these men are called PUSSIES, and are usually virgins who will die lonely (or married to a grotesque thing 30lbs heavier and 40 years older than them). You need to knock that shit off NOW.

I don't give a shit what your friends from the high school chess club told you. Women don't want a whining, insecure pussy who bleats on about his feelings and cries like a fucking adolescent girl. What can you do? Marlon Brando put it well: "YOU CAN ACT LIKE A MAN."

First, you say that when you're attracted to a female, you worry you aren't good enough. This is easy. YOU PROBABLY AREN'T. So lower your expectations.

Next, ACT LIKE A MAN. Go to a large party, gathering or gaijin bar. See any girls you think are attractive? Found one? Nope, you're probably too fucking ugly. Lower expectations, remember? So now try to pick out one you think inhabits roughly the same level of unattractiveness that you do. Preferably a lonely looking one with prettier friends. Found her? Good, now pound a few drinks and walk over and start talking. You do NOT talk about yourself, do NOT talk about your feelings, do NOT whine about anything. For once in your life, ask her about HER and stick with that conversation as long as possible because you already know you have a habit of focusing on yourself.

If you can manage to successfully man-the-fuck-up and get her into bed, then congrats...you've now established a baseline. You can score with a girl "that" ugly. Now, you work your way up. Keep trying it out with a girl just slightly prettier, until you've hit a level of attractiveness where you keep getting shut down. Then you know your limits.

I've just solved your life for you. Next, I run for President.

Alternative solution: one way or the other you flash your most attractive feature (I’m talking about the wallet here).
 
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I'm a little drunker now and had the chance to peruse the rest of OP's posts, and I think I've been able to put together a profile (again, I'm drunk). OP is an overweight and generally unattractive guy with severe confidence issues, a pronounced tendency to overthink things related to relationships, has probably never had an actual meaningful romantic relationship before and probably suffers from a pretty standard case of obsessive-compulsive-disorder. He has a tendency to create vivid, hypothetical romantic fantasies in his mind as he obsesses over certain females, all the while hating himself for being too [insert negative here] as an excuse for why he hasn't yet asked the girl out yet "but plans to." He probably stays up late at night acting out different roles and hypothetical situations, trying to build up his confidence, and spends enough time doing this that when he gets "rejected" (i.e., a normal guy asked her out and they're humping now) he feels even more dejected.

OP, you wanna know what works WONDERS for guys like you? Honestly? COCAINE. Obviously, I'm not suggesting you break any laws or anything along those lines, but I've seen a few shots of Chivas Regal and a couple of lines turn socially-backwards loser chumps into self-professed Don Juans....if only for thirty minutes at a time. But you come correct with a couple of bumps and I guarantee some lonely, chubby tag-along at the bar will definitely bob your knob in the parking lot after a few rounds. Get to work!

You should really be in charge of the « Dear Uncle » feature for a men’s site or mag. Answering readers’ letters about matters of the heart is your forte :D
(With Buta as a back-up)
 
Yea cocaine or Prozac or its modern day equivalent. Or we could all pitch in a 1,000 yen and have Yuriko give him a confidence building blowjob as her swan song.

I'd rather she ended on a high note. Getting booked for a 60-min appointment and then having the customer refuse to pull his pants down for 45-min and fret incessantly about how his dick might possibly be small isn't how I'd like to go out.
 
You should really be in charge of the « Dear Uncle » feature for a men’s site or mag. Answering readers’ letters about matters of the heart is your forte :D
(With Buta as a back-up)

Japan's suicide rate is high enough. I shall stick to writing useless, drunken babble on internet forums and inventing reasons why I shouldn't book Miran on my next trip to Tokyko.
 
OP, let me give you an example of what everyone is trying to tell you regarding your insecurity being your largest setback.

Fifteen years ago I was working in Osaka and one of my co-workers was, in my opinion, just about one of the most unattractive douchebags imaginable. He was an early-40s Indian guy who had emigrated to Australia in his teens and developed an infatuation with Japanese girls so he took a McJob with a big Japanese corporation and ended up in my office. Mind you, most of the expats in that office were in their mid-20s.

This guy was flat-out ugly. Skinny, almost emaciated, huge honking nose, bulging eyes, starting to gray, wore awful suits, but in his mind he was a Hindu deity's gift to women. He was a genuine douchebag and wasn't embarrassed about it. He was also a shameless pervert who would proposition ANYONE, from 16yo schoolgirls to 50yo housewives, not giving two shits how young/old/pretty/ugly/rich/poor/fat/skinny they were. He would start his day flirting with underaged girls on the train, spend his entire workday trying to score with Japanese staff women in the office and then the train ride home hitting on frustrated, middle-aged single women trying to (pretend to) sleep. Any moment spent not actually hitting on women was spent in the breakroom with the rest of us, talking about hitting on women.

And keep in mind that this was Japan, where a skinny, dark, ugly, middle-aged Indian guy making 250k/month is probably near the very bottom of the desirability totem pole.

And yet, every single weekend when we would hit the izakaya/bar/club circuit and run into this jackass, and he would be with some young-ish Japanese girl WAY out of his league, and I do believe he would tap at least a couple or three different asses a month.

Moral of the story? The single most important factor in picking up women is CONFIDENCE. Women do not want some whining loser who twiddles his thumbs, wrings his hands and cries about being lonely. Exude at least some level of confidence and the rest will work its way out.

Like I said, drink what you have to, imbibe whatever else fits your fancy then just get your ass out there and make the first move. And until you can do that, you'll be at home, alone, crying yourself to sleep.
 


How long should I wait? I felt I needed to get to know her well enough and see if there was anything between us before being able to ask her out. What if I invite a girl to coffee and she says yes, but it isn't enthusiastic? Am I supposed to act like we are still going to meet even though we both know we aren't? I don't know if there are any meet ups for people who like anime, video games, and manga near me, but I guess I can look into it. There is a video game themed bar I like going to. I plan to go there tonight by myself, I usually go with friends, and see what happens. I would say I am comfortable in my own skin, just very realistic.
 
Ummmmm... wow.

The problem here is not your friend. The problem is your social anxiety. You mention thinking that you need six months to be comfortable enough to ask a woman out... if a friend of mine mentioned a woman was cute and did nothing about it for months on end, I’d assume he wasn’t interested and she was fair game, just like your friend did.

Have you considered talking to a counsellor or therapist? A lot of people are hesitant, but they’re often incredibly helpful, especially for things like this.

How long would you say I should wait before asking a woman out then? Do I need to worry about any prerequisite or can I just go for it if I feel comfortable? I have saw a therapist over a decade ago, but no way I am going to bother with that here due to the social stigma and I think I feel be fine. A therapist would probably just repeat everything all of you have told me anyway.