I went sarging today. There was this girl probably in her 30s.
I asked her "do you plan on dating any time soon?"
she says "it depends. What do you do for a living?"
so as always, my gut says "tell her something to impress her. say engineer. say medical student"
then I remembered you have to say something ridiculous. so I said "I am an unemployed loser. I sit at home and watch porn all day"
this turned her off big time, she said "ok, keep doing that"
I tried to open her again but she said something like "stop harassing me" or "get away from me"

WTF? isn't that the way you are supposed to do it to be interesting? was I not being interesting or was she just dumb?

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I have not failed 10,000 times. I've just found 10,000 ways that won't work. - Edison

What did you say before that?

Plus, it could be a million other things. Maybe she's a golddigger. Maybe she doesn't share your sense of humor. Maybe she was dropped on her head as a child and is dumb as a result. Don't take it personally, it might be for the better anyway. If that kind of humor has worked for you in the past with the kind of girl you like, don't change it for one weird girl. If not, maybe you do need to change your humor a bit if it's not working with multiple women that are your type.

Don't overthink it. Personally, I think your line was a little lame since it's too easy to make fun of you (which doesn't matter anyway if you have a strong "i don't give a shit because I am the shit" frame of mind), but if you have had success with it, keep it up. Remember, everyone fails, usually pretty regularly.

Also, maybe your tone of voice was off and she couldn't detect the sarcasm (or she sucks at detecting sarcasm). I've fucked up stuff due to being tired or out of it like that. Tone of voice is very important as well as delivery.

Remember that sarcasm is difficult with strangers and unless they've got really good instant chemistry with you, it's difficult to pull off sometimes. If this keeps tripping you up, dial it back a little earlier in the conversation and be more straightforward.

Thanks for your thoughtful response.

That was almost the first thing I said. The conversation went something like this:
me: "what brings you here today?"
her: "blah blah"
me: "do you plan on dating...."
her: "what do you do?"
me: "watch porn, blah blah"

I am just wondering, was there anything I could do to save myself at that point?

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I have not failed 10,000 times. I've just found 10,000 ways that won't work. - Edison

No problem. Personally, I wouldn't jump into the dating line so early, but that's me. Sounds like maybe you caught her off guard ("I just met this guy, I'm not immediately sexually aroused by him and he wants to know if I'm single? I'll be a jerk and act like a golddigger and when he says something that shows he's not some rich fuck, as he obviously isn't, I'll get him to leave me alone by making fun of him or letting him know he's not rich enough for me, end of conversation"). Maybe.

I'd just play it cool. Be skeptical. As guys, we often fall into the trap of letting women screen us. We need to flip that. If your frame is that "I am awesome,and am a catch, is she good enough for ME?", things will change. Look skeptically at women, screen them, as if you're trying to find out if they're even cool enough to be with you. Women are a dime a dozen,even cool ones, so don't forget that. Who the fuck is she? Is she even intelligent? Didn't you just see like five other chicks you thought were cuter than her? even if she is cute, she's easily replaceable. Does she have a nice personality? Cause it seems like she may be just another stuck up know-nothing garden variety bitch who was raised to think she's special because she has a vagina that men are after and that she's not 300lbs or has a horribly disfigured face. You have to really ask yourself each time: is this person REALLY good enough to be with me? I need to find out.

I'd also spend more time in a dialed back, more chill state, just trying to be yourself and get to know them instead of worrying about cocky and funny lines when you haven't even known this person for more than 30 seconds. Get her defenses down first, show that youre a cool chill guy, and then once she feels a. Bit more comfortable around you and has removed that "total stranger" label from you in her mind (which can be within a few short minutes) wait for a good opportunity to say something like that, don't force it and say it just to check it off your "things I need to do to pick up girls" checklist. Just be a little more straightforward (esp with older women like this one, they're more straightforward at first especially, need less negging, teasing c and f at first than the younger ones do) but be straightforward with a skeptical "is this person even cool enough to associate with me, because I'm really extraordinary, most women would be lucky to be with me and I genuinely believe that." vibe and she'll pick up on it and react positively to your unspoken confidence. You won't have to worry about c and f, lines or game at all, you can just be your cool self while you screen this person.

excellent stuff. Thanks man.

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I have not failed 10,000 times. I've just found 10,000 ways that won't work. - Edison

Instead of making a joke about what you do (professional arm wrestler, circus performer, whatever), why don't you tell her what you really do? If it's not impressive, then maybe you ought to fix that before anything else.

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"Let me ask you something. If the rule you followed brought you to this, of what use was the rule?"