Okay here are the most practical tips I can think of for shy, introverted guys based on my experience. Free of charge
Bender's top tips for introverted guys
Start small
Rather than throwing yourself straight into the deep end, start with baby steps. This takes the pressure off and helps to start building momentum.
I think it was before I even started this journal, I did a mini challenge where I just had to ask one or two people for the time when I went out during the day. Once I was comfortable with that, I challenged myself to ask 5 for the time in 20 minutes. I did a few increasingly difficult challenges like that.
Another one I did was to speak to 100 people in one week. That seemed like a lot back then.
You want to be getting slightly outside of your comfort zone but nothing too challenging. Rig the game so you can win. And make sure you celebrate those wins. If your first baby step is to go out and ask two people for the time and you do it, be happy about that!
Other baby steps you could take are:
-Complimenting strangers. Next time you see a girl at the shop wearing a shirt you like walk up to her and say something like 'hey excuse me, I just wanted to say I really like that shirt...have a great day' You will brighten her day and make yourself feel better too.
-Ask people questions. 'hey, I was just wondering where you got that food from? It smells great' 'excuse me, do you know how to get to XY from here? I'm so lost!' 'where did you get that camera from? I've been looking for a new camera.' Doesn't matter if you only talk to them for a few seconds. The point is to just get more comfortable approaching strangers.
-If you want something really simple just go to a busy shopping mall, try to make eye contact with people and smile.
Find other guys to go out with
There is no way I would have made the progress I have made if I didn't have a group of other guys to go out and meet girls with.
I was lucky when I first started out one of my friends was at a similar stage to me. He was frustrated by his lack of success with girls and he was eager to go out and learn to talk to girls. So when I first started going out I had him to go out with. But not everyone has that luxury. A few weeks into this journal he met a girl while he was out one night and got into a relationship with her shortly after.
I didn't really have any other single friends to go out and talk to girls with so I was on my own. I did try going out alone at night a few times but that was pretty daunting back then, I needed more confidence to do that.
Luckily almost every major city in the world now has some kind of pick up lair. A pick up lair is just a group of guys who want to go out and try to meet girls. From my experience, most guys in the pick up community are shy, introverted generally nice guys. Some are a bit strange, a lot have very poor social skills but most of them want to improve.
I found a forum for my city's local pick up lair and messaged a few guys on there who sounded similar to me. Once I met these guys, they introduced me to other guys who introduced me to other guys..... Pretty soon I had a good group of wingmen I could call on to go out with me almost any weekend. Having these guys to push me, discuss nights out with and keep me accountable made a huge difference.
If you're hesitant to meet up with some unknown guys from the internet then there's a lot of dating companies that host seminars in major cities all over the world. Attend one of those seminars and find some wingmen there.
These pick up lairs and seminars attract guys ranging anywhere from 18 - 40+. Not hard to find them with a quick google search.
Get a job that connects with people
If you want to gain confidence talking to people, you will need to talk to a lot of people. One way to do this is to find a job where you come in contact with a lot of people. This may not be practical for everyone but if you're in a position in your life to work in a job like that, I would strongly encourage you to.
When I was in uni, I worked at bars for a while. Every night I would talk to a lot of different people, it was a good opportunity to talk to girls too. Now I do some work in sales. Every week I meet at least 50 new people and probably speak to over 100 people every week thanks to my work.
Go places where it's easy to meet people
Bars and night clubs definitely aren't the easiest places to meet people. You're contending with loud music, alcohol, other guys and a lot of girls will have their defenses up.
One place I've met a lot of people is a free running club held weekly in my city. A friend of mine has just started going to salsa dancing classes and met a lot of people there. You could also try gym classes, art classes, toastmasters, social sports etc... People expect you to talk to them at these places. And you don't have all the distractions of a nightclub.
As a natural introvert myself, I know I don't wake up in the morning and think to myself 'I can't wait to go to an art class today and talk to a bunch of random people!' If you're reading this, you're probably the same as me. But if you want to overcome your shyness and improve your dating life, you have to force yourself to do these little things and do them consistently. And honestly, it's not as bad as you think it's going to be.
Eventbrite.com and meetup.com are both good for finding events to attend and groups of people to meet up with.
Take care of your appearance
If you're hideously ugly you're at a disadvantage but it's not the end of the world. I think everyone has seen an ugly guy together with an attractive girl and wondered how that happened. Looks aren't everything.
That being said I'd definitely encourage everyone to take a little pride in their appearance. Not so much for the girls, but for yourself. If you look good, you will feel better about yourself and have more confidence.
With some work, I think almost any guy can make himself above average looking. I'm not the best looking guy but I've made myself reasonably attractive by exercising, eating well and dressing well (and I don't spend much money on any fancy clothes). These things, especially exercise and nutrition can make a giant difference to your appearance.
Go to a gym and learn how to squat and deadlift properly. If you have bad posture, try an exercise called the farmers walk. 1-3 full body workouts per week is all you need. Get your diet right - so important. Not just for your appearance but for your energy, mood and health in general.
Eliminate sugary and processed foods as much as you can. Get plenty of vegetables, especially green ones in your diet. You also need protein - chicken, some red meat, greek yogurt and cottage cheese are some of my favourite sources. Healthy fats are important too - sardines and fish oil are good for omega 3, avocado, olives, nuts and coconut oil are also good for fats.
Go to bed a little bit better every night
If you don't like yourself and you're not satisfied with your life, it's going to be very difficult for a girl to like you.
I'm always reading books, learning from youtube videos, eating healthy foods, exercising, trying to push myself out of my comfort zone. These things make me feel good about myself because I know they are slowly making me a better person. If you're doing these things consistently, you are already ahead of 95% of other guys.
Analyze your interactions
If you start going out and talking to women, take the time to go back and analyze your interactions. This helps build so much more awareness. I'd strongly suggest keeping a journal like this, even if you keep it private. Ask yourself what you did well, what you could do better next time and what you learned.
Try to focus on the positives. Celebrate small successes. I think you need a little bit of irrational positivity to succeed at this. But don't be delusional.
TAKE ACTION!!!
None of the above tips will improve your dating life or social life if you don't take action. If I hadn't started taking action, I would still be in the same position I was a few years ago - frustrated and lonely. Take smart, consistent action and it is basically guaranteed that you will be in a better position a year from now. The longer you wait, the harder you're making it on yourself. Start now.