I think it’s not so much that he approached a stranger or even that he overheard the conversation, but using his overhearing of the conversation as the whole pretense of asking her out.
“I heard you talking about how you need a date so here I am”
The problems are:
While you don’t expect privacy, it is still kind of weird for someone to explicitly mention that they were an unintended participant to the conversation. It amps up the awkwardness which is the last thing you want if you are trying to make someone comfortable. She may very well be explicitly aware that her conversation was overheard, but it’s something that can be put aside, except it was explicitly brought up.
Further, the rationale makes it sound like he thinks she is doing her a favor. The takeaway is not “you seem interesting/attractive and I’d like to get to know you” it seems more like “you seem like you are in need and I could do you a favor by taking you out”. That takeaway is going to feel like the offer makes her just seem more pathetic, like a “pity date”. Particularly in front of her friends, any whiff of a “pity date” will trigger being defensive.
Of course the story is probably all a fabrication, but taking it at face value I certainly see how it is ‘off’.
Ibuthyr@feddit.org 5 hours ago
Thanks for typing it out! Half of the people here apparently have never dated or had fun the old way, without apps. In fact, it’s downright sad to see that basic human interaction is dying out. These skills that everyone kind of had to learn in the past transfer to day to day life. Many younger people are just not pleasant to be around in the office because they have zero social skills.
sp3ctr4l@lemmy.dbzer0.com 4 hours ago
The wild part is that I’m not even 40 yet.
And, I am literally autistic, struggled with socializing a fair bit in middle and high school, and then forced myself to learn social skills in college, in part through going to bars and learning how to be a wingman and such.
Like… what I have described is the 101 stuff, lol.
Maybe I’m just… too good at masking, or something? I dunno anymore.