The best short, easy resource on what I mean is this book: https://party.pro/book/. The Art of Gathering is another good one if you want to go deeper.
You may be concerned that you don't know many people, so can't easily organize an event where people would come. This is actually solvable (see the book above). The nice thing is that this also lets you risk and experiment with social failure ("what if people don't show?", etc), which in my experience is the cause of a lot of social anxiety.
The first half of the meeting is where people give prepared speeches and get evaluated. The second half people have to give a 2 minute talk on an improvised topic.
You'll meet people in a supportive and friendly environment, improve a useful skill, and have lots of fun.
There might be conventions where you live. There's all sorts of themes like sci-fi or food & wine expo, you can have loads of conversations there.
If you have a skill you want to learn like "how to bake bread/ brew beer / make chinese food" then you can go to artisan markets and ask for advice in achieving your goal, people are generally happy to give advice also it will get you out of the house and give you an interesting thing to say for your next encounter.
- You can't rely on anyone else to have fun so you have to talk to people or you're bored
- Alcohol helps lower your inhibitions so it becomes easier (relying on it always is no good but alcohol can be a tool just like any other thing)
- if you say something stupid or someone has a bad reaction or doesn't wanna talk you can say "have a good one" and peace out
If you don't know where to start with talking to people, comment on something they're wearing, then ask them followup questions and be genuinely interested and try to make jokes. If you run out of things to say, "have a good one" and peace out
Great way to learn to read people too because often people are too polite to tell you to fuck off but their body language suggests it so I learned to pick up on a lot of more subtle cues I didn't really see before
Or go to openings at art galleries/museums. Go to fairs and festivals. Really, any local event that is open to the public.
Now, the techniques... sometimes it helps to arrive early, so that as people walk in to the event behind you, you can greet them. This is much easier than walking into a room of people and trying to figure out how to insert yourself into the conversation. Come up with a line of questions other than "what do you do for work?" that you can use to engage people beyond yes or no questions. Look around the room for people who are wallflowers and use your shared shyness to break the ice. Look for the people who are the life of the party and float with them - they may help introduce you to other people just by being in the same conversation circles. All this takes time and practice just like any other skill.
Random interactions are going to be hard and awkward. It's much easier to be part of a group that you know the other person has at least some of the same things in common as you.
- Get a dog! Seriously, going to dog bars, dog parks, and even walking the dog are all great opportunities for spontaneous social interactions.
- Group fitness classes can be good, even if you just chat with the instructor before or after class. Going regularly you're bound to talk with some of the other members.
- Arts classes (i.e., pottery) can be good, as it's usually a small group setting and you can chitchat while you're working.
Not the question, but another thing to consider is your body language when you're in those spaces. Try to be cognizant of it and present yourself to being "open" to conversation (especially in a bar setting). By that I mean, looking around, make eye contact, smile at people, don't be on your phone, and don't be afraid to say hi.
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Meeting people just like that is a bit difficult. But if you have something to offer, like, "hey I have some time on my hands and I'd like to volunteer", I think people open up to that.
If you want to kick it up a notch, try travelling some distance without a smartphone and relying on others for information.
Meetups are designed to foster interactions with strangers. So are networking events and the like.
Volunteering is another option. You'll be paired with a bunch of strangers for a few hours.
You can also hit up your local subreddit and invite a few people to some activity. Just pick something you like and ask if other people want to join.
The "enjoy" part was pretty key for me - as I feel like it's really hard not to be my best self when I'm having fun and more focused on the activity than making a good impression. I also tend to do well at things I enjoy, and that gives a helpful little self-esteem boost.
I think you should lighten up on that goal. Meeting hundreds of new people for a person without social anxiety would be difficult. Maybe just start by chatting up folks who cross your path in everyday life? You might not get to hundreds. At least you won't distract yourself with unrealistic metrics.
You can replace ‘dog’ with any social hobby, I guess. Surround yourself with people who share the same interests.
Also, "hundreds of people"? IRL is not twerk tic, most people don't have hundreds of IRL friends, or even "had" in the days when IRL was where ALL friends were...
Step 1: Go to places you like, and talk to the other people there...
Then apply this muscle to less ephemeral situations like the coffee shop or gym or whatever, where a group of people are in the same general area as you for extended periods of time, with their own demands on their time, likely there studying or exercising or whatever. When they get bored studying or exercising for a bit, say something to them. Like "Yo what's up, just studying?". Are you worried about how you "sound"? Or if you are saying "the right things"? If you are work on letting go of that. It's a huge weight on your shoulders.
Also, if you're working. Start pinging people. People love talking about stuff they're interested in. I do it and learn all about all the crazy hobbies people have. I've actually taken up hobbies myself as a result of some of these interactions because I met some /extremely/ dedicated people.
It's fucking easy man. Just do it.
With this tactic I guarantee you will have 100 interactions in no time.
Thoughtful comments appreciated with any downvotes.
In the end I got so depressed I forced myself to started going out on my own to meet people.
I mostly went to bars, but I found other places I could make friends too like parks and festivals. Early on I tried going to meetups and things like that, but honestly I wouldn't recommend them. Everyone (including myself) tries so hard at those events. It's better than not socialising at all, but it always felt way too forced to be fun for me. Plus, these meetups don't exactly select for normal people...
Anyway if you're interested I guess I can give you some tips from what I learnt going out and socialising on my own several times a week for over a decade...
- Find somewhere you like.
The most important thing when trying to make new friends is to feel comfortable. If you're at a bar you hate you'll give off bad vibes and the people who are there to have a good time won't want to be around you.
If you don't like bars, most cities will have festivals and other things going on during weekends which you can try out. Another thing I'd do in my city in the summer was go to parks because often there will be groups of friends drinking and listening to music that you can try to talk to.
But the important thing is to just find a place you enjoy being. And don't feel you need to commit to anywhere either. I'd often go to several different places before I found somewhere I liked the vibe of and suck around.
- Have no motives.
By far the biggest mistake you can make when trying to make friends with people is actively trying to make friends.
People can tell when you want something from them and when you're not being genuine. If you're talking to someone and run out of things to say just end the conversation with a "nice meeting you" and move on. A forced conversation is always a bad conversation. But a good conversation that comes to an early end can easily turn into a second or a third conversation later. And this actually a better way to go about socialising in bars because the more independent interactions you have with someone the more they'll feel they know you.
- Start topical conversations.
There's lots of BS out there about the best way to start cold conversations with people, often with elaborate strategies, but by far the most natural way is just to comment on something topical. Personally I'd be observant of whats was going on around me and if I saw something interesting – or thought of something I wanted to share – I'd say it to nearest person. So if you're in a bar and some guy yells at some other dude, that's a great time to turn to the person next to you and ask, "what was that all about?".
By far the best conversation starters are ones that in addition to being topically relevant say something about yourself and ideally highlight some kind of shared value between you and the person you're speaking with. If you're at a bar and you hate the song playing and you can see someone who also hates the song, that can be a great way to start a conversation. "ehhh, this song sucks right?" – and the same obviously works in reverse if you both clearly love a song.
A higher risk move but one I enjoyed was to comment on what other people were wearing or doing. If you're trying to talk to girls then this is about as close to a social hack as you can get... Girls love to chat about how some other girl at the bar is falling out of her dress, or how awful some guy's shirt looks. Saying something, "omg, what is she wearing?!" can be a great way to start a conversation with a girl in the right context, but context is 99% of this working well.
- You don't always have to start the conversation.
There are techniques I found to start conversations without actually starting the conversation myself. One I did a lot was to just look bored. If you're in a social environment and you're on your own looking bored people will often approach you and ask if you're alright. In which case you can say, "yeah fine. I'm just on my own." Then sometimes people will just say "okay" and go back to doing whatever they were, but often they will feel bad and come chat to you for a bit, or invite you over with their friends.
The other thing I'd recommend is trying to stand out in some way. Typically I tried to wear clothing or an accessory someone might comment on. I wouldn't recommend going too crazy though because then people might think you're weirdo and avoid you, but what I found worked well was to be over dressed for the occasion. Another things I liked doing was to wear an unusual colour, so I'd sometimes wear a pink shirt for example. This works because very occasionally people will comment on what you're wearing, but more importantly you can bring it up yourself and show some social awareness – "am I over dressed?" or "you don't think this pink shirt make me look gay do you?". Another thing you could try is wearing a band tshirt which someone might comment on. Again I often did this as a joke by wearing a joy division tshirt then I'd ask people if it was okay for me to be wearing a joy divison tshirt when I hated their music and only liked "love will tear us apart". If I were to guess as a guy if you want to a bar wearing a Taylor Swift t-shirt you're probably guaranteed to get someone ask you about it. Whether you'd want to do that I dunno, but you get my point.
Same thing applies with items. If you can carry an item that either people might comment on, or you can use in conversation then great. A silly example that comes to mind was once I found a shoe on the floor so I carried it around with me for a bit. Some people asked why I was carrying a shoe, but it also allowed me to start funny conversations with girls by telling them I was looking for my cinderella.
- Don't ask for numbers.
This isn't a hard rule, but generally I wouldn't ask people for their contact info even if I thought we were getting on. If people want to be your friend I can almost guarantee they'll ask you for your number.
What I'd typically do if I wanted to reconnect with someone was just to mention that I might be going to some event on my own and see how they react. Or if you're at a bar you could just say you'll probably be going there next week. If they want to hang out again they'll probably suggesting coming with you and ask for your contact info.
- Have fun.
Something I realised after a few years of trying to meet people was that making friends wasn't actually what I enjoyed. What I really liked was just having fun with people. The more you can get away from the mindset of trying to make friends, and more you can just do things in the moment that make you laugh, the easier it becomes to make friends. If you think about people who are really good at making friends, they're probably also fun people who like to joke around. Being able to entertain yourself is probably the most important skill to being likeable.
Dunno if this is helpful to you or anyone else... Also for what it's worth I'm from the UK. I'm guessing in the US it's a bit easier to talk to people, especially in the day.