I've had multiple conversations with women who are somewhere between disappointed and despondent that guys don't hit on them more.
>I mentioned to several of the people I interviewed for this piece that I’d met my husband in an elevator, in 2001. (We worked on different floors of the same institution, and over the months that followed struck up many more conversations—in the elevator, in the break room, on the walk to the subway.) I was fascinated by the extent to which this prompted other women to sigh and say that they’d just love to meet someone that way. And yet quite a few of them suggested that if a random guy started talking to them in an elevator, they would be weirded out. “Creeper! Get away from me,” one woman imagined thinking. “Anytime we’re in silence, we look at our phones,” explained her friend, nodding. Another woman fantasized to me about what it would be like to have a man hit on her in a bookstore. (She’d be holding a copy of her favorite book. “What’s that book?” he’d say.) But then she seemed to snap out of her reverie, and changed the subject to Sex and the City reruns and how hopelessly dated they seem. “Miranda meets Steve at a bar,” she said, in a tone suggesting that the scenario might as well be out of a Jane Austen novel, for all the relevance it had to her life.
https://www.theatlantic.com/magazine/archive/2018/12/the-sex...
I think the solution that leaves everyone happy is: start a conversation with that woman, but if she's not interested, leave her alone.
Look at it in utilitarian terms:
* If the woman you're talking to isn't interested, your attempt to start a conversation will create a brief unpleasant experience for her.
* If she is interested, there's a chance at a great, long-lasting romance which will benefit both you and her.
The positive utility from finding your future spouse is much larger than the negative utility from a brief unwanted conversation. So on expectation it often makes sense to start that conversation.