I'm younger than you, but I used to have similar issues. I think you have to realize that you're a worthy human being and don't need to seek approval in back-up friends. People "smell" neediness and low-self esteem: do something that makes you proud of yourself and stop listening to social pressures of any kind. You don't have to become a jerk, but seek balance.
Insecure men also struggle with their manliness. This is usually a taboo topic, but you need to address it and be sincere about it: do you feel emasculated? "Without saying it goes that I still don't have GF or wife. I am 29 and getting near 30 is a bit scary." There are more people than you realize in your same situation; worse, there are people who married early and are now stuck in a loveless, bleak marriage. one of my mentors – I respect him so much! – found the love of his life in his late 40s, after an awful, awful marriage.
You're a free, young man in his quest for manhood and respect. Just like everyone else. :)
On the subject of manliness, get to the gym. Lift some heavy weights. It will do wonders for your testosterone levels which will in turn boost your confidence and esteem. As a bonus you will also look better and feel better.
This is true, if you can get over the fact that results will come very slowly, and that, in the gyms I've visited at least, most of the people there are already ripped and can make you feel somewhat inadequate.
The upside to the "most people are already ripped" is that even though you may feel inadequate those guys are pretty non-judgemental about you/others. Everyone started somewhere and my experience is that the gym is pretty judgement-free.
I've been going to the gym for the last year or so and it's helped me through a few tough times. I like the simplicity of it, even though everything else in my life might be chaotic I can spend a couple of hours at the gym forgetting about it, making myself feel better and getting healthier in the process.
I felt a little uncomfortable my first few times in the gym until I realized that the really serious people saw me the same way I tend to see programming interns -- not looking down at all, just cognizant that they are further down a certain road. They've been helpful and encouraging to me, just like I try to be when the subject is programming. Really, it's much scarier to think about not going to the gym, than going.
Results come a lot quicker for beginners. If you are feeling intimidated about going to the gym at first, it would be worth getting a personal trainer who can show you the ropes and get you started on a program. It gets rid of the fear of being that beginner who has no idea what they are doing.
True, going to the gym should be a permanent lifestyle change that should be kept for at least a couple of years. As for the ripped people, they all started off somewhere too. Nobody gets to look fit for free.
I found martial arts a more bearable way to get more exercise and not get bored. Started out with karate and then picked up Brazilian Ju Jitsu, which is a lot more full on and arguably less structured. Both did wonders for how I felt about myself as well as putting on some muscle and losing some fat.
No, you "don't need to address it". That stuff is just bandaid.
I struggled with my "manliness" until i realized it didn't matter. You don't have to match up to standards of masculinity to find friends and/or dates.
EDIT: of course getting good exercise is still a good idea for its own sake.
(dropping in mid thread here, hopefully I'll be clear where I'm talking directly to the OP and where I'm quoting other people in the conversation)
I was in a similar-but-not-identical position to you some years ago (around your age actually, I'm 36 now and things are going fine) so can relate to the feeling. I think most people feel this way at points in their lives.
> you're a worthy human being and don't need to seek approval
This is a significant point. First make sure you like yourself; from there social confidence does not come from believing other people will like you and want to hang around with you, social confidence comes form knowing you'll be perfectly fine if they don't.
Don't take that as "it is their loss" or "I'm better off without them" because those are negative trains of thought which will make you seem (and feel) arrogant, instead try use the frame of mind "well, that didn't work out, shame, but fine, lets try something else". The more relaxed attitude to things not working out as desired will reduce any air of desperation you might be giving off which will help you be more comfortable to be around.
> > I also feel resistance when I ask someone to go out on outings
There could be many reasons for this. People have limited time, especially those with GF's/wives and families. Adding new people to their social circle may just seem like something they don't have time for right now, and if that is the case it isn't a slight against you personally.
It may also be that what you are suggesting just isn't their thing. Have you tried finding like minded people outside your current family and work circles? If you have hobbies then finding a local club relating to one of them is a good way to meet people with whom you more naturally have something to talk about.
> Insecure men also struggle with their manliness.
I didn't read a specific "manliness" issue here, but rather a more general "socially awkward" one. The rest of that paragraph are on point though: there are many in the same boat, many in far worse situations because they fell into something less than ideal, and finding the right people simple isn't predictable. I say "right people" not "right person" there as I don't believe there is one right person for anyone - there are a number of people you could love, a number of people who could love you, and there will be more people in the compatibility cross-over of that venn diagram than you might fear.
> > I still don't have GF or wife
I suggest not worrying overly about that, if you try too hard to make it happen you'll look desperate and either scare people off or attract the wrong sort who are out to take advantage. I've been single for a little over a decade now (initially burned by a long term relationship that went sour so I locked myself away a bit, more recently just because the right situations haven't occurred (or when they have it hasn't worked out)) and it really isn't a problem. Concentrate on finding friends, if something else happens after that then that is a bonus. Heck, once you develop close friends they might introduce you to people they know who that might work for you with.
If you are specifically worried about that and feel it is something that is missing form your life you could try things like speed dating, I know a couple of people that has worked out well for. Everyone in the room knows they are in a similar position in the respect and the event is regimented which removes some of the awkwardness of approaching each other, and the worst that can happen is that you've lost a couple of hours of an evening and it might help you to go and realise the range of people who do turn up including people who you might otherwise assume could just walk into a bar and pull on command.
> > What is wrong with me, seriously ?
Almost certainly nothing more than is wrong with the rest of us!
> There could be many reasons for this. People have limited time, especially those with GF's/wives and families. Adding new people to their social circle may just seem like something they don't have time for right now, and if that is the case it isn't a slight against you personally.
This is a critical point. My dear dead grandmother had a supremely wise rule of thumb: "If people are being weird or cruel, it's probably due to something that's up with them, and not something you did." People are so wrapped up in their own problems. They can't help it, none of us can, we're trapped inside ourselves and our own perspective, everything we do and feel seems so important to us that we naturally assume it's a primary cause for other people's actions and reactions, too. Humans sometimes take this really, really far... They think that if they are bad, they'll offend the god(s) and get struck by lightning. Nowadays many people mock belief like this---any notion that nature or the universe somehow care what you do---but even the staunchest atheist can still be caught assuming that everyone else's bad moods, cruelty, indifference, and poor behavior are primarily due to STUFF THEY DID. This rule of thumb can seem depressing---nobody cares about me!---or you can view it as freeing, consoling, calming. Which is how my grandmother (and now I) mean it. Someone being cranky? Someone doesn't want to hang out? Don't jump to the conclusion it's because you did something. Maybe they are just worried about bills. Maybe they just really have to poop. Rejoice that your own bowels are fine and look for someone less grouchy to hang out with.
Insecure men also struggle with their manliness. This is usually a taboo topic, but you need to address it and be sincere about it: do you feel emasculated? "Without saying it goes that I still don't have GF or wife. I am 29 and getting near 30 is a bit scary." There are more people than you realize in your same situation; worse, there are people who married early and are now stuck in a loveless, bleak marriage. one of my mentors – I respect him so much! – found the love of his life in his late 40s, after an awful, awful marriage.
You're a free, young man in his quest for manhood and respect. Just like everyone else. :)
Lastly, let me link you to a post where I addressed my insecurities: https://news.ycombinator.com/item?id=8745651
If you need an e-mail pal, reply to this post and I'll give you my contact information. :)