No but really. What is the difference between intentional and unintentional harassment? How do you ask him that? What kind of question would you use? How do you detect lies?
2-4 aren't super interesting. I'm not agreeing, but it's just not useful to continue.
Lastly, I think it's obvious you're a little bit younger than the other commenters. That's no sin. Young people don't always think through their actions, especially how they might be received. Case in point, edge lord humor, which often uses deadpan sex and racial references; someone who faces sexual and racial threats frequently is more likely to be bothered by those kinds of "jokes" and might not understand it's supposed to be a joke. Since we don't carry forms detailing what topics bother us, it's often best to avoid those kinds of jokes. It's not censorship, but instead a courtesy we can extend to others. Caring about others is not a failing.
I would urge you to keep in mind who your audience is, that there are jokes you can make to friends that are different than those you make to acquaintances, and remember inflection and tone don't transfer well in text. Mistakes do happen, and so do consequences.
The reason most of us are on high alert, is there are countless instances of women being raped, beaten, and/or murdered by men with "a strange sense of humor." Where the women reported concerning behavior and the instigator was given a stern warning, and then the woman is found a week later in a field. I keep pressing the intent question because this method doesn't work at identifying bad intent.
When you make someone uncomfortable with your words, you might not have thought the knife was sharp, but someone did get cut. Your intent doesn't change the fact you hurt someone. We might not call the cops, but we might ask that you stop showing off your proverbial knife or not come around any more.