For me, it was a long talk I had with a random person on Omegle when that was a thing. I was bored one night so I decided to give it a try and I was matched with someone who I had nearly a 2 hour conversation with. We told jokes, told each other about ourselves, and talked like we were lifelong friends. But, we never did tell each other our names. I could’ve talked to this person all night but the interaction turned for the worst near the end. The person was depressed from what I gathered and the depression arose and the conversation fizzled out. I still think about them nearly 6 years later and hope that they are doing good whoever they were.
Slow day at work, called a Dell support rep to deal with some equipment that needed to be replaced and ended up talking with them for 2 hrs. I think they must’ve been bored too because I remember telling them directly that we could end the call or keep talking if they wanted. They not only were comfortable with it but said they’ve never just chatted with someone.
Same idea as OP, it was like catching up with an old friend.