The point of going on a date is getting to know somebody better because you're interested in them. Why on Earth would this woman be interested in this weirdo who she knows nothing about except, at most, that he sat alone at a bar for three hours straight, listened to her conversation, and interrupted her to ask her to dinner on the premise that she needs saving from being single specifically by him?

Stories like this are presented from the POV of the guy, even from that perspective it's not 'good', at best it's just not 'bad'

There's nothing wrong with asking but also like don't just drop it out of nowhere.

Even if the vibes are right, you can't just walk up to someone, say 'wanna date?' and get good results. That's especially true if you open by saying you were evesdropping.

Chat with someone for a bit, see if you click before asking them on a date. Even just buy them a drink and give them the option to approach you.

She was a massive dick, but that doesn't mean he handled the situation well.

The point of a date is not to get to know someone new. It's to get to know someone romantically. Some people want to know a little bit about someone before they are ready to decide if that's something they're interested in.

It's not always "that" you ask someone. Sometimes its when you ask.. or how, or what you say.

Also... what world are you living in where talking to someone you haven't previously met, in a bar, is a social faux pas?

It's not inherently. That's why the sentence had more words than just the ones about being strangers. I expect you to know how to read sentences given your comment is a fucking wall of them.

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.

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 he 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'.

No, walking up to and interrupting a group at a bar after listening to them for three hours, telling them you've been listening, then asking one of them to dinner next week like they need saving by you is extremely rude. No one's saying you aren't allowed to talk to strangers; you just shouldn't be this goddamn weird and intrusive about it.

"How are you supposed to find a partner?"

Get to know the strangers first in a capacity whose end goal isn't a date, then ask them out when you know them somewhat? Or ask a stranger out at a place and in a context where it's expected they might be open to it? Anyway, I'm going to go ask out random women on the street, because it's not rude; I mean fuck, man, how else can you find a partner in this economy?