“Hey, I heard you talking about wanting to date. I’ve been feeling the same way and wanted to see if I could get us a couple drinks?”
That’s still bad because this is still pretty weird, but just be a bit casual about it instead of: “M’lady most fine, I heard of your plight and wish to save you. Please allow me take you out to dinner next week.” She’s with her friends, sure, but it sounds like she’s been bringing down their night by complaining, so they probably wouldn’t mind if she (somehow) said “yes”. And the suggestion itself involves way less commitment than planning a date.
This still happens, but you also still need to be suave about it, which anon was not.
“Hey, I heard you talking about wanting to date. I’ve been feeling the same way and wanted to see if I could get us a couple drinks?”
That’s still bad because this is still pretty weird, but just be a bit casual about it instead of: “M’lady most fine, I heard of your plight and wish to save you. Please allow me take you out to dinner next week.” She’s with her friends, sure, but it sounds like she’s been bringing down their night by complaining, so they probably wouldn’t mind if she (somehow) said “yes”. And the suggestion itself involves way less commitment than planning a date.