Find people that are not "boring" for you.
You're not "supposed" to be doing anything special. Just find someone comfortable. You should be interested, not fake it.
If you are not comfortable in a situation, don't think that you "should" be. Find a situation that FEELS comfortable for you.
Maybe you have trouble to open up? Talk about yourself, what you think. what you want... Don't be afraid of the judgment of others. If they want to judge, it's their problem. Everyone is human and others can relate to you, your stories, your ideas and problems.
Maybe you (wrongly) believe that others have nothing of value for you. If you were smart in your childhood, you might have picked this bad habit of thinking you are more intelligent than others. Realise that everyone is different and people around you actually have a lot of things, ideas, informations to share with you, you can learn a lot from others. You can discover new ideas, new perspectives from them.
First, identify your goals: what do you want from people? Why do you think you should engage socially with others?
Second, a great way to meet interesting people is common interests. Join a social thing: chess club, rock climbing, music concerts, book club, dungeon and dragons, video games, workplace, dog park, gym, even drinking or smoking.. etc it's endless. Talk with the people from that social circle about the social thing that brings you together. (ex: talk about chess) Start with something, and as you interact more with a person, you will find if you are comfortable or not with that person. (not everyone fits with everyone) As you interact more with someone comfortable, your range of discussion topics will increase.
Source: I was a loner in highschool but when I started a computer program in university I was happy to meet a lot of like-minded people and it felt a lot more easy to connect with them since they shared my hobbies and interests. The same thing happened when I got into electronic music. Finding a passion, then connecting with people who share it.
Silence is also ok with someone you are comfortable with. Watch a movie together for example, or play a sport together, that is still interaction.
Groups can also be more easy than one-on-one.
Practice, put yourself out of your comfort zone. The more you do it, the better you will get at it. If you are shy with women, push yourself to interact with women. (friendly) Same with men.
Source: I also did that for many years before I finally became comfortable with women. Just pushing myself to talk with them, even if what I said was completely dumb the first times.
If you feel something is "very wrong", you can consult a psychiatrist or doctor for more personalized advice. You could have something like Asperger's, but that doesn't mean you cannot make friends.