How to stop being boring

Joke's on you, OP - even being like that you'll still find people who think you're boring because it's subjective.

Truth is, once youth passes, over time people become increasingly disinterested in others. This effect was exacerbated by the recent pandemic.

You might be a genuinely fascinating and authentic person, yet all that is going to fall flat in a crowd whose reaction to going outside is "ugh, people".

What really works is showing genuine interest in others. It's such a rare thing in this day and age that many are surprised when they experience it.

I read a book that said you should try something new to you at least every quarter if not more often. It gives you something to talk about.

While my wife and I are empty nesters and at point where we travel a lot and we do the digital nomad thing in spurts so we can always talk about travel or more often ask “what’s the most interesting place you’ve been to”/“What’s interesting about where you live” etc, it doesn’t have to be travel.

And just to be clear, it’s always either guys I am striking a conversation with or couples. There is no way for a 50 year old married guy to talk to a woman alone at the bar without coming off like a creep.

On the other hand, I try not to talk about politics or religion. What’s the point?

2. People often vacillate between conformity and contrarianism. This is what juvenile edgelords on the internet are about. Both conformists and contrarians are trapped inside the same silly paradigm. Both define themselves and behave not in terms of the truth, to which all intelligence and behavior must conform, but in relation to others and what they think. A conformist assumes a persona that agrees with others in their social setting, regardless of whether it is objectively good. A contrarian takes what agrees with others and negates it, regardless of whether it is objectively good. Both are mindless, reflexive, and boring. Both lack substance. Both are empty theater rooted in people-pleasing and approval-seeking. Both are dishonest, cowardly acts of deception.

3. Reading a room isn't about people-pleasing. It's about empathy so that you can response in the way that is good and needed. If you enter a funeral parlor, you don't crack jokes or paint your toenails. You recognize there are people grieving there, that a dead person is being honored. In other words, you also consider, within reason, the good of others in the room, and you respond to the facts as they are, even when pursuing your own goals.

4. One flaw in the "I gotta be ME!" schtick is that it idolizes the self. It makes a god of the self. It puts unmoored desires above the truth instead of rooting desires in the truth. There are plenty of desires that ought not to be indulged, at least not indulged in certain ways or at certain times. The point is that your behavior ought to occur within the scope of reason. What is evil and wrong is always outside of reason.

5. Life can be messy. We can be messy. When that is the case, the goal isn't to keep messing it up or to run with our own mess toward the abyss. These messes, our mess, is a kind of cross we bear for the good. They're things we struggle with, not surrender to. If someone has a tendency to overeat, it might be difficult to resist, but it is good for him to practice fasting. If someone has a habit to reach for porn, it may be painful to resist, but it is good for him to resist and to avoid so that he can overcome the habit instead of wallowing in slavish submission to that awful vice. If someone has a tendency toward irascibility and wrath, it may feel satisfying to indulge it in the moment, but practicing meekness is the true reward. If someone has trouble with envy, tearing someone down may scratch that itch, but responding with selfless good will is freedom. Triumph over vice makes us interesting. Succumbing to its easiness makes us boring.