Take at your statement, and pretend a frustrated/easily embarrassed/grumpy person is hearing it:
"You look like you could use some help" --> "You look like you don't know what you're doing/you look frustrated"
"I may be able to offer relevant expertise" --> "I assume that I both have something to offer and that you are having a problem of this particular way/shape/form"
"in the interests of addressing your apparent problem" --> "whatever you're working on is clearly broken, and needs fixing"
My formulation is intentionally very gentle and indirect, precisely to avoid any of the above misinterpretations. Working with people experienced in the field or who are known to be open to communication, obviously, we want to be more direct; for a novice, or for somebody who is looking for any excuse to take offense at what you're saying (perhaps because they're frustrated at their work and want to vent at something), it is useful to take a lighter touch.
I should hope that's precisely not the point unless you just want to frustrate people more. The approach you describe is, in my considered opinion, possibly indirect to the point that could be by some considered to be influenced by Dadaism. Let's model a hypothetical person focused on a problem they're struggling with:
"Hey, do you have a second to chat?" --> "I want to waste your time with spurious bullshit when you're clearly eyeball-deep in something."
Might I suggest a different formulation that presumes less about the subject? Or perhaps giving up entirely? Personally, I've accepted that there is not and cannot be any uniformly acceptable way to approach a stranger and offer assistance that does not risk backlash or misinterpretation.
And then you and your space are attacked publicly as being a place where nobody respects focus, men are constantly approaching women, and so on. Or someone blows up after being quietly and kindly asked that for the fifth time in two hours by well-intentioned people who are unfortunately less than omniscient and an article entitled "Woman harassed in hackerspace by brogrammers!" hits Jezebel.
Communications failures combined with the human capacity for reinterpretation are a bottomless pit of potential badness.
Maybe I'm just more cynical about people than you.
This sounds a lot like black-and-white thinking or all-or-nothing thinking (psychology).
"If I ask a woman in a hackerspace ``want to chat?'' then .... Jezebel will print horrible articles about men."
"If I don't talk to the woman in a hackerspace then..... .. .. I am a horrible misogynist (?) because I am not encouraging her."
From Wikipedia, "Splitting creates instability in relationships because one person can be viewed as either personified virtue or personified vice at different times, depending on whether they gratify the subject's needs or frustrate them. This, along with similar oscillations in the experience and appraisal of the self, leads to chaotic and unstable relationship patterns, identity diffusion, and mood swings." I think sometimes folks get too invested in how to talk to women in tech. Do your best and move on. No one is going to fix this problem individually, and heightening every interaction into a chance for a Jezebel article is counterproductive. Not unless you are Iggy Azalea are you going to get Jezebel hate every time you move, so relax a little!
An environment has been created where the slightest of perceived infractions is maximally punished. You'll have to forgive me for not wanting to take that risk just because someone asked nicely. It's become quite clear to me that doing my best and moving on isn't good enough.
Have you considered the possibility that there's a real state of fear surrounding these topics? It renders everything toxic and every interaction becomes a minefield. It's not a healthy state of affairs, and it's not one in which telling people to do their best and move on offer is a sufficient response. It comes across as utterly lacking in empathy.
Take at your statement, and pretend a frustrated/easily embarrassed/grumpy person is hearing it:
"You look like you could use some help" --> "You look like you don't know what you're doing/you look frustrated"
"I may be able to offer relevant expertise" --> "I assume that I both have something to offer and that you are having a problem of this particular way/shape/form"
"in the interests of addressing your apparent problem" --> "whatever you're working on is clearly broken, and needs fixing"
My formulation is intentionally very gentle and indirect, precisely to avoid any of the above misinterpretations. Working with people experienced in the field or who are known to be open to communication, obviously, we want to be more direct; for a novice, or for somebody who is looking for any excuse to take offense at what you're saying (perhaps because they're frustrated at their work and want to vent at something), it is useful to take a lighter touch.