How to be More Fun / How to be Less Boring
I didn't think so at the time, but back in the day I could be a pretty boring guy to hang out with. Here are some ways you can be more of a fun person:
Actually do things when you're with people
If there's one thing that identifies more boring people, it's that they never seem to be doing much. If you were to go to, say, a staff party, the more fun people would be making the rounds talking to their coworkers, joking around, maybe dancing, and generally having a good time. On the other hand, the more boring people can be found sitting at a table staring off into space, watching the dance floor but never joining in, or being physically in a group or conversation but not engaged with it.
In other situations it's the same thing. In a pub or restaurant they're sitting with everyone but not talking. At the weekly poker game, the more boring guy is technically there playing with everyone else, but he's not really saying much or making himself noticed.
There are other ways you could describe such people. Maybe they're shy in these situations, maybe they don't know anyone, maybe they're not having fun, maybe they don't know what to talk about, maybe they don't know how to dance, maybe they think they're being cool by hanging back, or maybe they're distracted by other concerns. These things could all be true, but if you're looking at them from the perspective of wanting to have a good time, you can't help but think of them as boring.
You can go a long way towards being more fun if you just make an effort to participate when you're out doing things with people. Often that's all you have to do. You don't have to buy a loud Hawaiian shirt or be the "crazy" guy who's high-fiving and back slapping everyone to be seen as a fun person.
Also included here is being open to new suggestions. If a bunch of people are hanging around and one of them suggests doing something, new or otherwise, it's often the more boring person who doesn't want to do it. They want to keep doing the same things as always and aren't up for a change of pace.
There are several reasons why you might not be participating more already. You may not have the skills or knowledge to take part. If everyone is talking and you're not good at conversation then joining in is easier said than done. If everyone wants to dance but you're hopeless at it, then you're resigning yourself to watching on the sidelines. What if everyone is talking about something you're not knowledgeable about? What if you could just stand to be more interesting? What if you decided to work on these things?
You also may not have the desire to join in. You may not like what everyone else is doing. You may also not like the people you're with and not be particularly motivated to jump into the action. I've been in my fair share of situations where I wasn't much fun because I told myself the people I was with weren't my style and that I didn't enjoy hanging out with them. The obvious solution is to improve your attitude about people. If you find you dislike most activities except for a handful of them, it may help to branch out a bit.
You can see here that you may have a longer road ahead of you than you thought. If you're a bit boring because you tend to have a bad attitude towards people (e.g., they're all are shallow and superficial, you're different, you're deeper, no one understands you, you're not on their level, blah blah blah) then you have to overcome those issues first. That doesn't happen overnight. Maybe your attitude is fine, but if you realize you're lacking in some important skills, like making conversation or being able to talk to strangers, then you have to take the necessary time to get yourself up to par.
Don't be so picky about what you require to be entertained
A boring person out at a bar could just be shy or not know what to say, but they could also be thinking something like this:
"I'd dance but music isn't very good."
"I'd drink but it's too expensive."
"I'd talk to people but they all look stuck-up."
"I'd talk to people but it's too loud in here."
"I'd talk to my friends but they're all being annoying right now."
"I'd have a good time but this bar sucks."
And don't forget the most ironic statements of all:
"I'm bored."
"This place is boring."
"The people I'm with are boring."
Thinking back, I've been this person more times than I'm comfortable with. While I was complaining to myself, my more fun friends were out there dancing, drinking, meeting, talking, and having a good time, despite the supposedly less than ideal conditions. Make the best of whatever situation you're in. Focus on the positives instead of the negatives. If you can only have fun under the perfect circumstances then what's the point?
Don't sit back and wait for the amusement to come to you
This is related to the above point. Another big trait of more boring people is that they never make their own fun. They depend on the situation or other people to provide them with entertainment. If they go to a party they won't take the initiative and try to meet some new people or get involved in a fun situation. Instead they'll hang back and wait for people to come talk to them or rely on their friends to keep them interested. If the friends get distracted by something else and no one interesting chats to them, then the boring person will become resentful and not have a good time.
More fun people know how to amuse themselves. Hopefully the situation will be fun from the get-go, but if it's not then they'll stir something up. They'll meet some new people. They'll suggest something to do. They'll inspire other people to be more fun themselves and see where it leads.
I also remember being bored in various places and having all these 'if's running through my mind. "If the DJ starts playing better music I'll have fun. If I was at (some other bar) I'd be having fun. If my friends start acting a certain way I'll have fun. Until those things happen I'll remain bored." I was totally passive. I thought I could only have fun if things largely out of my control flowed towards me.
Don't be so serious
Being too uptight has also contributed to my being boring in the past. I'm sure it has for many other people. Recognize any of these?
"These people are so shallow. Why don't more people want to have deep, intellectual conversations?"
"Drunk people are so annoying."
"Ugh, everyone's being so loud and obnoxious."
"Why are those people dancing like that? It's so embarrassing."
"I can't believe my friends are doing that, what a bunch of idiots."
"I'm too mature to do that."
"Eww, this place is so hot, and loud, and smelly."
"Do these people really think this is amusing?"
And on and on. Having fun often involves letting loose and acting more crazy than you normally do. Even acting slightly reckless and idiotic (according to my old, uptight standards) sometimes led to a good time. You can't bring rigid, serious, humorless sensibilities to fun situations.
Lighten up a little. That doesn't mean you have to drink fourteen beers and go streaking at the next party you go to, if you're more restrained yourself that's fine, but it's not the end of the world if not everyone else is. Try to take yourself less seriously too. Don't think you're above letting yourself go and acting 'immature' or whatever. Above all, don't think being smart and mature, and being a fun person are mutually exclusive. Being able to joke around and have a good time doesn't cancel out or diminish your intelligence.
Bring something to the table
Just following the suggestions above can cut a big chunk out of your boringness, but you may need to add something to yourself as well.
One thing you can do is just become an all-around cooler, more socially adept person. That's the whole point of this site, yadda yadda yadda.
The most fun people have one of more things they contribute to the group. Some are really funny, some have a knack for leading everyone into crazy adventures, some have a lot of great stories, some know all the best places to go, some have a lot of fascinating things to say, some have a knack for introducing people to new ideas, etc etc etc. Is there anything about you that makes you more fun? Is there something about you could develop further?
Be fun in your own style. Let your fun self be a reflection of what you're like normally. Maybe you're more of an amusing companion type rather than a zany center of attention. Don't feel you have to live up to some caricature of what a fun person is like.