I get that Klopp seems a pretty progressive guy but I feel like if there are people seriously questioning the sincerity of his well-wishes to Hendo, well, I feel like you are setting yourself up for more future disappointment projecting your feelings like that. Don't forget the amount of time and days he has been working side by side with Henderson the past 8 years, that's a long time. Nevermind the rollercoaster of emotions and experiences they've shared.
As much as we the fans can make out we have a deep connection with the players, the reality is they are only ever one unfavorable transfer move away from that bond being severed. I understand there is more to this one but it's still true. That's not the case for Klopp or people who know him personally and will genuinely want Henderson to be doing well in life and happy.