Does anyone even care ?
Burdened, burned out, hard working, sensitive and ever running men are always taken for granted. Most men don't express their loneliness due to social constructs. What do you think? Does anyone even care about male loneliness?
Not my place, but everyone should leave out thought of being judged and just speak to people. Just initiate conversations with people you don't know.
Everyone has a different story to tell, and so much to learn.
Find a less creepy way, of course
While watching a reel of Alakh Pandey, he shared an incident where a girl entered his office building, inquiring about the PW office at the ground floor to security. Both Alakh Pandey and the girl took the same lift, and when he asked whom she wanted to meet at the PW office, she ignored him with a rude expression. If she knew him, I doubt she would have reacted this way.
The question remains: how do you differentiate between a creepy approach and a gentle one?
We cannot / not liable to correct people's upbringing. Even if we didn't know him, we would have given some answer probably vague to ensure security. But then that's us.
Gotta move on from such people