If not a jerk, then grossly lacking in sensitivity, empathy and tact.
The reality, the beauty of human relationships is that they are between people with all these issues and dimensions, all the nuance and detail that make up human beings. In the wild, there's no laboratory people - no clean, perfect specimens in simple environments.
My rule is, I don't know what someone else has been through and is going through. Never, ever judge. If absolutely necessary (e.g., I need to decide to partner with them or not), make my best guess but don't judge.
imo, people often take what people say literally or default to a first-instinct interpretation, rather than trying to understand what the speaker is attempting to convey. I try to interpret what people say charitably (a few of my friends think much too charitably), but I really believe that the vast majority of people seldom intent any malice in their comments.
In the example, it might have been intended in an empathetic way - "Damn, sorry, I didn't realize you were still hurting. I would have extended a shoulder to you if I realized". Or a pragmatic way - "I think the situation isn't as bad as you think, want to talk about it?" It could have been bluntly honest (personally, I typically appreciate honesty over politeness) or a totally aloof statement made on reflex. It could also just have been someone being a jerk, but I suppose the point of my rambling is that there's a myriad of ways to interpret a comment, and it's largely based on both the speaker's experiences and how they communicate.
I find that the person I'm talking to, if I treat them as if they are a*holes, act as if that was their intent the whole time. If I treat them as if they in good faith, they act that way.
It's hard to resist the flow of conversation, to not go along with the way it's framed. I think that's why people act how you treat them; I think that's why people even confess falsely to crimes - the interrogator talks to the suspect as if they did it. Other sophsticated communicators also use that intentionally.
Empathy comes from being able to put yourself in other people's shoes. Reading fiction has been shown to increase empathy. If so then these guys need to do more reading.
Not things I'd be inclined to talk about when those things are ripe for opening myself up to discrimination.
I once interviewed at a medium sized, name brand Silicon Valley darling everyone on HN has heard of, where an interviewer outright asked me if I was married and if I had kids! Like, holy shit, just read your interview training manual! The very first sentence is probably "Do not ask any questions where the answer would even imply information about things that would get us in trouble discrimination-wise." Yet this person overtly asked! Here I was in the stairwell walking down to the second floor and she hits me up with one of the few totally forbidden questions! I thought about saying "What would HR think of that question?" but the asker was the HR manager! Totally bonkers.
An interesting strategy?
This case is strictly worse because the questions are explicitly being asked to evaluate eligibility for hiring.
Are you a virgin?
I could definitely see arguments for asking these sorts of questions in how they could be job related but not worth the legal risk
I haven't had (nor ever likely will) have the luxury of working somewhere where potential/smarts is too relevant past a relatively low threshold
Are you suggesting that this is bad? What do you hope to gain by seeking out obnoxious people with traumatic backstories and broken families with yuck problems? Misery loves company?
Obviously performance is also a critical factor but your comment gave me the impression that you don't see any value (or even harm) in targeting charming people without yucky problems. They do indeed sound like "perfect" colleagues to me!
Screening for people with life stories that you/anyone deems acceptable is extremely problematic, because realistically you will never have access to deeply personal information about 90% of your coworkers. As in, you should not be forcing Janet from accounting to disclose to you that she was abused by her stepfather, because if she is a well-adjusted adult it would have absolutely no bearing on your interactions with her at a workplace
All else being equal, a person who enjoyed an idyllic childhood is typically going to be a more well-adjusted adult than someone who experienced the most depraved, violent, extreme child abuse imaginable.
I don't even have any interest in discussing the finer points with someone who completely denies the long-term effects of adverse childhood experiences.
We are talking about specifically work-related scenarios, that usually have pretty straightforward boundaries and surface-level interactions. "All else being equal, a person who enjoyed an idyllic childhood is typically going to be a more well-adjusted adult" - not necessarily in this specific context, people that didn't experience trauma are not immune to being awkward, immature, neurotic, anxious and various other things that makes working with them difficult.
That is not to say that people who have experienced childhood abuse can't have issues with basic human functioning. The point is, neither are necessarily are better or worse to work with just based on their trauma or lack of thereof.
It is irrelevant that people with normal childhoods are statistically more likely to be well-adjusted in most aspects of their lives, because we are only considering workplace interactions.
But as it relates to actual work? No.
Usually the answer to a single resume gap is something personal and none of my business as an interviewer, it's not my place to pry if you were raising children, caring for dying relatives or battling severe depression
It'd be a pretty easy win.