Tinder was a paradigm shift. It’s success around 2015 started to flip public perception of online dating. Suddenly it was for all kinds of young people that were looking for the convenience of profile matching. A rising tide lifts all boats so legacy platforms shared in the popularity, also getting runoff from the non-target audience of the newer apps. The change in perception of online dating allowed people to appreciate its pragmatism. We’re in an age of busy people optimizing their lives. The structure and accessibility of online dating just fits with those kinds of people.

In school I had a physics teacher who thought it was a good idea one day to use whiteboard markers on the glass windows instead of the whiteboard. I didn’t learn anything that lesson.

Social skills, as the name implies, are meant to be trained, maintained, and expanded over a lifetime so don’t discount yourself because you feel like you’re too old or have tried and failed for too long. Have you considered seeking behavioral therapy? Perhaps you’re not picking up on the myriad non-verbal social cues that could help you better inform your conversations. Behavioral therapy can help identify where you’re lacking and give you the opportunity to practice skills and receive feedback from a professional.

I sincerely wish you the best of luck.

You don’t need to give explicit details of your coworkers’ lives, but from your writing it really seemed to me that you were more interested in mechanically optimizing conversation. This isn’t necessarily a bad perspective, but people already do that organically by understanding each other more and learning their history. The route of good conversation follows logically from there through empathy.

You’re descriptions kind of make your coworkers like NPCs. If you want to have better conversations you should probably get to know them better as people. That can allow you to understand the why of their particulars and eventually guide your conversations more organically.