That sounds to me like someone who would have been open to a conversation about being sensitive from the very beginning had it been approached differently. I certainly don't think we can reasonably discount the possibility. I recently saw that Jaffe commented on the Hemingway controversy and suggested that political correctness was neutering free expression. That suggests to me that Jaffe didn't actually learn what we might have wanted him to learn from the incident. When you have the freedom to say anything you want but voluntarily choose not to because you're sensitive to how someone else feels, and don't feel any resentment for making your choice, that's the goal we should hope to achieve with an individual.
The danger of my saying any of this is it might be interpreted as a "tone argument," which is frequent derailing technique. Someone reacts angrily to an offense and someone else tells them that their response took the wrong tone and tries to defuse the anger without addressing the complaint. That's not what I'm intending here. I'm concerned with tactics, not tone.
There have been some very measured and positive responses to Hemingway's comments, including this opinion piece by Brandon Sheffield where he writes "Eventually, with enough blowups like these, we may eventually not need to have them as often." A blowup is a loud calling out of an offense. And at the very beginning, I agree we need to have those in order to establish the problem.
I think we're already past the point of needing blowups. For those of us who care to pay attention, the problem is bloody well established. The seal on this conversation has been inexorably broken, and only the most intransigent and stubborn observer who is completely closed to reason can deny that the problem exists if and when we go through the litany of examples that demonstrate its existence.
That being the case we're at the point where real communication is possible in the face of incidents like Hemingway talking about "girlfriend mode" and Jaffe dropping an unfortunately-phrased quip about blowjobs. I do not think it's safe to assume that everyone understands just how sensitive people can be about these sorts of off-the-cuff, no-harm-intended comments, and there are ways to educate them other than making them feel stupid or slapping fighting words on their actions like misogyny.
It isn't about coddling people. It's about practicing what we preach. Offensive speech pisses us off because it means the person is being completely thoughtless about what they're saying. They're not exercising any sensitivity to how other people might think about their words. But do we automatically ask ourselves, before we react to statements like "girlfriend mode," if the speaker really had any clue why they might be about to offend someone? Sensitivity is not common sense. It can appear that way to someone who's versed in social justice but it's not something everyone has ever been engaged with or by.
Considering the ultimate root of these problems is lack of gender diversity within the development community, I think it makes a hell of a lot more sense to open with engagement with developers who make problematic comments rather than arriving at engagement after a fit of pique that feels good but doesn't establish the understanding everyone wants. Getting upset does inspire conversations, but it sometimes inspires counter-productive conversations and eventually shuts down dialogue with individuals who might otherwise be reached.
Unless one wants to argue that these teachable moments aren't precious, I think we need to grab every one of them we can get and lead with the assumption that everyone has a better nature to appeal to. Showing patience is exhausting, isn't as sexy for page hits or as satisfying as screaming our outrage, and wears on anyone who tries to change things for the better, but it's still necessary. We should at least try once with everybody. And if we know they know better because it's not their first trip around the mulberry bush, then let loose the dogs of war.