How do you engage in a meaningful conversation with someone?

Find others who are disconnected from Social media. Find common hobbies or things to do or discuss about together.

Examples. Working on a project at home or a hobby like team sports. Maybe cycling etc.

Dump being connected and find real human connection.

At least that’s worked for me.

We’re evolved to have in person connection in groups.

I can only have meaningful conversations with those I feel a connection with

Those bore me too.

I seem to have lost that ability, or I haven't met the right people in the last couple of years.

I usually just ramble until we connect on something to talk about

Turn it into something like a Book club. Find a BOOK about a topic you care about and get a group of friends together at your house once a month to drink wine, eat cheese and fruit, and talk about the topic of the book!

I really don't know anymore. It used to be easy, but I don't meet interesting people IRL. They don't have stories and ideas, just gossip.

I'm not sure anymore. For the most part, I just don't, so I can't help you.

Maybe you just not chatting with the right people

It rarely happens to me

occasionally

Meaningful conversations? That's so 2019 ...

Good conversation depends on the person you are talking to. It's that simple. ☺