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I wasn't necessarily disagreeing with you. My comment was to show a different perspective, not to dismiss or argue against yours. Or rather, not all of it. Cause I do agree on the "Sorry" VS "opt-out" part.

If I didn't know, but I assumed someone didn't want to date me I wouldn't ask them out. If you're operating "under the assumption that the other person doesn't want to talk to you" why are you wanting to date them? I only want to date people that want to at least talk to me.

Here I would add something, though. If this person doesn't see a path to success with any woman, I don't think he should necessarily give up, because at least some of the "There's no way it'd work" would be false. Some will be correct, but because of the constant rejection the guy faced, he will be assuming all are under the "There's no way it'd work"-umbrella. So if he stops pursuing a relationship in general in order to avoid women who will reject him (which, in his mind, would be everyone), it'd become a self-fullfilling prophecy: He thinks no girl would be in a relationship with him, therefore he stops trying, therefore no girl would be in a relationship with him.

To be clear though, I'm not advocating for asking out someone who is actively avoiding you, or someone who already made it clear in some way that she's not romantically interested. Like if you confess and she says no, he should give up, yes. But not before it's confirmed that his suspicion is correct. I've been rejected many times, all times so far, in fact. I have always stopped the romantic approach towards that person once I knew they didn't like me romantically. A couple I'm still friends with to this day. Others that I wasn't particularly as close with before, no, especially once the thing keeping us together ended (as an example, a high school crush after high school was over).