Be patient.
Do all/most of the other things mentioned in this thread, but don't expect things to magically get better overnight.
Go out there, and embarrass the shit out of yourself. Be awkward. Then go home, and do the same thing next time you go out.
At some point, you'll notice that hey, this isn't as hard as I thought.
As to what to talk about, just talk about the things that interest you. Something that you're passionate about, if there's such a thing. Talk about ideas you have, realisations you've come to lately, things you've noticed, things you like.
And don't forget: Be brave enough to embarrass yourself at least once a day.
Good luck!
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Step 3a: Start saying yes to any social opportunities. Co-workers invite you to bar? Say yes. A classmate asks you if you want to study with them? Say yes. A friend asks you to go out to dinner with them? Say yes. The more you say yes to people the more you will get invited out and the more friends/acquaintances you will make.
Step 3b: To get more comfortable in social situations you have to seek them out. Just like how you have to practice to get better at piano or how you have to go to the gym to build muscle you have to practice being in social situations to get more comfortable with them. So don’t just wait for other people to invite you out, actively seek out opportunities. Ask people if they want to come over to watch a football game, ask people if you can tag along with them go to the bar, the worst you will hear is no.
Step 6: Life is short so don't be shy. We're all going to die one day "memento mori", so ask yourself if any social gaffes or embarrassing situations will really matter in the end. You will die, I will die, everyone you've ever met will die, even this planet will die one day. Nothing is permanent, everyone and everything will come to an end. So please keep this in mind the next time you feel nervous about asking a friend to dinner or the next time you feel nervous about asking a cute girl/guy for their number. You get one life so don’t be afraid to take risks and try to make the most of it. Nobody on their deathbed wishes that they had stayed in the comfort zone more and taken less social chances. You get one life. It's okay to fail, it's okay to embarrass yourself. In 100 years nobody will remember either way.
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You have to set up achieveable small goals and focus on those, at the same time working on self-acceptance and picture everyone else having the same struggle as you, just with different variations; strenghts and weaknesses.
In my case it was making eye contact with the cashier, making baby steps toward small talk by always focusing on politeness (saying «no thank you» or «yes, please» when asked about plastic bags, receipt, etc - kindness and politeness is a superpower! You’ll realize how it makes other people comfortable and that way creates a safer space for you).
I started taking initiative to be more vocal in social situations - again focusing on what’s manageable. Maybe saying hello and goodbye audibly is a proper goal - maybe something else like complementing someone’s hair or clothes. Acknowledge people (and yourself as a part of the situation) by sharing more of what’s going on inside you. «Thats’ a good idea», for instance.
After over 15 yrs of working on my social skills I’ve actually ended up in a part time sales job in a high-end store while finishing a degree in architecture.
I never quite got over my insecurities regarding romantic situations, but just enough to keep hanging in there until I met a wonderful woman who is kind and makes me feel safe and accepted.
Finally, now as a 37 year old male on my third educational journey, I’ve started taking antidepressants and going to a psychologist as well. I have not only been shy and introvert, but also depressed - basically being mean to myself in my head and denying myself happiness for over thirty years.
It’s never to late!
Tl;dr: baby steps
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This is a small tip but take it or leave it. A little lesson (simplified) in human psychology is that people will react differently to you socially depending on the nature of your approach.
I.e. if you walk up to someone thinking they are a stranger in your head, approaching them like they are a stranger, saying a few quiet words like they are a stranger... they will most likely react like a stranger. You won’t get many positive cues, (unless they are overly extraverted) and the convo will most likely end quickly and maybe awkwardly.
However if you can change your mentality about your relationship with people you don’t know very well, and treat them (in your head at least) like you do a close friend or parent that could REALLY change how your interactions go. So another example for instance.. the next time you are walking into a social setting approach people mentally with the closeness of a sibling or best friend... it’s not as important what you say then that matters. Don’t worry about filling the silences.. or having all your lines practiced in your head.. just walk up and talk, ask them how they’ve been, what they’ve been watching on tv lately, etc and then quit thinking about what your going to say and just listen. Asking questions is the easiest way to keep conversations going and you can continue that until you find something in common you want to talk deeper on yourself. It’s all sunshine and rainbows after that.
In this situation there is nothing to fear but fear itself. If you want to be more social you’ve got to put yourself out there and just be you. Some people will like you some will not, who cares.. You’re not going to turn into an extraverted super hero alone at your house browsing reddit. Get out there.
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I've been learning a lot about setting & defending personal boundaries this year. In certain ways, I'm very much a follower & tend to go with the flow, partially because I suffer from chronically low mental energy & it's easier to let things slide than it is to fight it.
There's the old saying that the only reason introverts have friends is because an extrovert adopted them at some point. Growing up, I realized that I spent most of my time at social events waiting for someone to come & talk to me, and eventually the lightbulb clicked & I realized that a LOT of people were in the same position, so if I was the one to initiate, they'd probably open right up!
Eventually I worked up the courage to start talking to cashiers at the checkout line, and discovered that they were usually bored at work & ignored all day by customers who just wanted to get in & get out. The more I practiced, the better I got at initiating conversations.
Now, many years later, I won't shut up! lol. My wife thinks it's hilarious how much I blab to everyone we run into, whether it's a waiter at a restaurant or a clerk at a store. It's mostly just practice & easing your way into it, and coming to realize a few facts:
No one really cares about you but you. People generally forget dumb stuff we do, whereas we tend to remember it forever haha. Most everyone is focused on that same inward-anxiety feeling themselves! We create a mental fiction that everyone is judging us & criticizing us ALL the time, when that's not the case at all!
There are some emotionally-insensitive blockheads who will publicly criticize you or laugh at you. For some reason, that criticism becomes as prominent as a solar eclipse in our heads in terms of our emotional reaction in the heat of the moment. Generally, people who do this are just verbalizing what they see without meaning to be jerks, or ARE jerks & want to be mean, or are gatekeepers & are highlighting a boundary violation they see. In any case, recognizing that we have the freedom of choice on how to respond & how to feel can give us some perspective over those emotional hammer-times that we run into throughout the day!
Recognizing that we get exposed to good, bad, and neutral all day, we can plant the seed for not letting the stream of daily experiences define us by choosing how WE want to act & behave by default, proactively, rather than just letting the day dictate letting others take control in a reactive way
If you're open to taking a little field trip, I've been working on the idea of a cow-catcher (the big metal rake triangle on the front of a train) in terms of how to get through a day as reserved people who want to be more outgoing:
I'm still an introvert, which simply means that I have a social battery, and when it runs down, I'm ready to be done being out & ready to be home recharging. But there is a difference between being an introvert & being outgoing! I discovered that I'm actually HIGHLY social, when (1) my social battery is charged up, and (2) after having slowly exposed myself to the practice of chatting with people over time to the point where I was comfortable initiating conversions, asking questions, smiling, and even being OK with silence without feeling the pressure of awkwardness.
One thing to try out is to ask people about specific things using closed-ended questions instead of open-ended questions. For example, "how's your day?" vs. "did you have anything crazy happen today?" or "how are you?" vs. "can you believe the weather today?" Once that initial conversation ice-breaker gets cracked, everybody LOVES talking about themselves, no matter how closed-off or anti-social they may be, because even people who have no major hobbies or interests at least have favorite books, TV shows, and video games that they get fired up about, and really, most everyone has some type of involvement in a work thing or a hobby thing or whatever that they like to chat about!
It's hard to explain, but as you practice, you'll pick it up & you'll start to understand the nuances of (1) opening the door for people to talk by being the first one to talk & being kind to them, as many, many people are just waiting for someone else to start the conversation but can't quite get over that hump, (2) asking closed-ended prompting questions to get the ball rolling, and (3) learning how to read the vibe of the room, as nearly everyone I've ever talked to connects to that "hey, you're not gonna womp on me & you're a normal person & hey I don't mind having a normal conversation with you" mental dimension.
Basically you have to be the one who plugs in that cord to plug into that regular-person conversational dimension, because then people will open up once personally invited & put their I'm-in-public shields down. We all tend to wear a metaphoric mask in public, like at work, at school, at the grocery store, etc., so everyone kind of goes around with walls up all the time, but it's on pretty thin ice & it's fairly easy to crack once you get a little practice with it & build up some confidence!
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