Most difficult imho would be to explain why we haven't advanced any further. If the person is 50 in 1950 he started with horse carriages and saw development to intercontinental bombers, rockets etc. The landing on moon would astonish him, advances in medical sciences and computing too but he probably would ask: "And what are you using that neat little gadgets for?"
I'm using this little gadget for all my banking needs, a significant amount of my shopping, to stay instantly connected with friends/family and strangers with common interests all around the world, to almost instantly find information on almost any topic, to watch any of a hundred thousand movies or TV shows instantly on demand, and it's also a telephone.
I think you're severely underestimating how our daily lives have advanced. We've advanced so far that we don't even regularly use the thing that would blow the mind of someone from the 50s, like calling someone on the phone. Calling someone with your phone would already blow their mind, because the first handheld phone didn't happen until the 70s. But we don't really call people anymore. We send instant messages or if we want "a call" we do video calls, which is guaranteed to blow their mind because a) most people in the 50s had a black and white television, so being able to see colored picture in real time is just next level shit, b) you can see someone else in real time on the other side of the planet and c) it's going to feel like you're there because the image quality from the 50s is like a cave painting compared to what we have today. And that's just calling someone. Imagine what else would blow their mind, modern cars probably.
Also, remember that the previous generations versions of a “phone call” was the mail, or sailing across on ocean, or being carried by a horse, or even walking for years or decades to get to the person you want to make contact with.
Maybe I'm underestimating individual benefits of digitalisation. But I tried to remember talks with my grandfather. He was born in 1912 and lived to the age of 87. He could remember the coronation of the last austrian-hungarian emperor Karl. People then were not as individualistic as we are today. Technological, social or cultural advancements were seen more on a collective scale. The mere possibility of calling or texting someone didn't impress or astonish him much. Especially in the 50's and 60's promises of a bright and shiny future were made. Just think of the exploration of space or the deep sea with proposed bases on moon, mars or the seabed. It wasn't called the atomic age for nothing. What I experienced was that those now long dead relatives appreciated the individual improvements of their lives but they felt a certain slow down in regard to an overall progress of society.
He probably felt the same way about video calls in 1998 that I do now about ChatGPT4 performing coding to run single cell RNAseq. Mind-blowing, but quickly adapting to and using the platform.
This I disagree with. Porn has always been widely available throughout human history, it just wasn't as widely openly available and distributed as today.
Case in point, my grandfather died in Vietnam back in '63, all of his barracks stuff went into a box that was sent home. My grandmother never opened it, to the extent it was still sealed with navy tape from the 60's. When she died, my father didn't even know it was in the attic.
When he passed back in '15, I was cleaning out this attic and found the box. Ontop some actually really cool shit- you guessed it, I found a literal shitload of vintage porn. Grampy was dropping loads left and right with these bitches. A LOT of hair back in the day I might add.