Listen, I don't think her son has bad intentions here but I'm tempted to bet money that he's going to put his foot in his mouth in the process.
This. I mean, if he was going to NOT put his foot in his mouth, one signal would be his ability to wait for this conversation to a time when he wouldn't be interrupt her time with her friend.
I'd also want to qualify that . . . I don't think he CONSCIOUSLY has bad intentions. But it's coming at least partly from a self-centred impulse. Maybe he wants to check on her, maybe he wants to reconnect, maybe he wants to greet her new friend, maybe he even wants to apologize in some way, but with this timing none of that really makes any sense outside of a kind of patronizing but insecure need to emphasize that he's the centre of the family universe. I mean, about the BEST possibility is something like "I want to give my endorsement to whatever you're doing and be supportive--and obviously you NEED my endorsement before you do anything, so it's OK for me to interrupt whatever you're doing in order to give it." And it gets worse from there.
Admittedly, not even Hanayo initially planned to have Yoshiko over after their date, so his timing would not have been that bad based on what he knew. And it is her birthday, so it does make sense to try to still visit her on the actual day after his original plans fell through. Nothing to do with Yoshiko whatsoever - although things may well change once he meets her, I do agree with you both on the direction his foot is likely to take.