Some Things That May Happen As You Get Better Social Skills
As your social skills and self-confidence start to fall into place you may notice your perspective on certain things changing. People will also react to you in ways they never used to. There isn't a ton of advice in this article. It's a bunch of observations that may give you some insight into how more sociable people think, and how your own viewpoint may shift as you become more like them.
People will still assume things about you based on a first impression, but different ones than before
Anyone who considers themselves socially awkward probably has a few unflattering assumptions that people commonly make about them. Like someone might conclude they're a sterotypically dorky programmer just because they're quiet in group conversations. If they improve their social skills, and their interaction style changes, people can still jump to false conclusions based on a superficial impression, just different ones. It goes to show you can't really escape that kind of stuff.
Amusingly, the stereotypes they're hit with may be the opposite of the ones they used to get. They may talk about a recent night out at a pub and someone will assume they're just some generic bro. People may think they're dopey and happy go lucky just because they're more joking and laid back now. They may start to dress more sharply, and someone might believe they're superficial and care about nothing but fashion.
You may start to have a harder time relating to more unsociable attitudes
This one doesn't happen right away, but if you improve your people skills you'll eventually get to a point where it will be years since you got over the worst of your problems. When that happens you may start to lose touch with some of the old attitudes you had toward socializing. For example, previously someone might have hated making small talk, but now they're okay with it. If a friend complains about it they may think, "Wow, did I used to be like that? Did small talk bug me that much too? It's fine. What's the big deal?"
They may even find themselves getting peeved when they hear someone express an opinion they used to have themselves, but no longer relate to. Like they may hear a co-worker talking about all the events they have to attend over the Christmas holidays, and how they resent all the forced socializing they have to do. Even though the previously awkward person used to hate Christmas parties for the same reason, because they're fine with them now they may think something like, "Come on, suck it up buddy. What's so hard about having to chat to your colleagues or relatives for three hours? It's supposed to be fun."
You'd think someone who's been there themselves would know better. That's human nature though. When we've moved to a new place in life we can lose touch with how we used to think. Sometimes it's due to that unempathetic thought process where as you get better at something, you start to take your skills for granted and forget what it was like being a struggling, discouraged beginner. At other times a more socially savvy person may be too mentally invested in no longer being like their past "loser" self, and they overcompensate by looking down on anyone who used to be like them.
It's not always that extreme thankfully. Often someone will have a quick knee jerk reaction, and then a split-second later remind themselves, "Whoa, whoa whoa. I shouldn't be so hard on them for not liking staff parties. I was like that myself one time. I know where they're coming from."
What's scary is that if someone who's been there themselves can be unsympathetic toward less-sociable attitudes, imagine what it's like for people who have always done well in social settings. They don't have much much sense of what it's like to feel uncomfortable in their own skin. They'd tend to conclude if someone doesn't want to socialize, it's because of some flaw they have, or because they're choosing to be less-social to be a jerk, not because it's difficult for them.
When you tell people you used to be a dork, they may look at you blankly
If someone has decent social skills now, but feels they used to be a big dweeb, they'll sometimes mention it in conversation. The reaction they're looking for can vary: to gain sympathy, to bond and establish common ground, to be funny, to look humble and self-deprecating, to get a free pass on any blunders they may make in the future, or to fish for a compliment. Revealing this information often doesn't get much of a response though.
Maybe people see through the hidden agenda. Maybe it's obvious someone used to be a dork, so the information is redundant. Or maybe it's clear they no longer have social problems so the information is irrelevant.
People relate to you based on what you're like now. In a way they have a hard time imagining you were ever different from the person standing in front of them. If you come across as fairly likable and put together, playing the "I used to be a dork" card doesn't really register.
It's also pretty cheap and meaningless to claim you used to be a loser. Genuinely charming, attractive, popular people say they used to be dorks all the time, or that they still are ones deep down. Even if they mean well, it can be hard to take seriously. It can come off as either pointless insecurity, or an insincere attempt to say, "Hey, I'm just like everyone else!" Terms like "dork" are also so subjective anyone can say they once fit into that category. Isn't it something of a joke that two thirds of people will tell you they were awkward in high school? So if you used to be a quote-unquote "real" dork, and you bring it up, everyone may figure you weren't that bad, and you're just making a play to seem relatable.
When you talk to shyer or more socially inexperienced people, you can see the effect outgoing types have on them
Most of the people reading this site know firsthand what it's like to feel awkward when they have to speak with someone who's more confident and outgoing. You can really start to appreciate the effect when you're the self-assured, outgoing person, and you get to see the interaction play out from the other side. Maybe you'll be in a friendly mood one day and start chatting to someone who turns out not to be very comfortable with that kind of thing. As you talk to them you'll pick up on their body language, and because you've been there yourself, you'll have a good sense of the thoughts and emotions going through their mind.
In that quick exchange you'll see how off-balance and on the spot they are. How they want to get away and for the conversation to be over. How they're struggling to think of what to say. How they're overwhelmed and maybe a little intimidated by you. And it may not even be that you were ultra-outgoing and cornered them for five minutes. You could have just said something like "How's it going?" or "How's your day been?", before realizing they weren't having fun and dropping it.
You can appreciate the mindset of being the chatty, friendly person who just wants to talk to everyone
On a related note, you may get to know a bit more about what it means to be in an outgoing mood. In the past you might have sometimes gotten annoyed by friendly people, but you may come to get a sense of how they think, and why they sometimes act in the seemingly oblivious way they do. That mentality of, "I feel X, so everyone else must too" comes into play. In this case it's thinking, "I feel like talking to people. I like talking. Everyone likes talking. People are nice. Why wouldn't they want to talk?" At that moment you lose some of your ability to appreciate that not everyone is on the same wavelength as you are.
You'll get better at accepting social compliments
When people start to become more socially adjusted they can start to get offhand comments that they're funny or interesting or whatnot. At first it's easy to be a bit taken aback and not believe these compliments. You can think, "No way that's true. I'm still a total dork." With more time you (more or less) learn to take these statements at face value. Your self-image tends to lag a few years behind how you are in the present, but it will eventually come around, and accept that descriptions like "fun" aren't total mismatches with what you're actually like.
You may have to reject some people yourself
And it isn't fun at all. If you've been rejected in the past you may think it will taste oh so sweet to be on the other side and get to be the one turning people away. Nope. It's uncomfortable and often makes you feel bad. As you improve your social skills people may start trying to befriend you, and you won't be interested in all of them. Also, if you get pretty good at chatting in a friendly, engaging manner and making a good first impression, you can unintentionally send people the signal that you want to be friends with them, when you're really just like that with everyone.