Maybe it’s worth considering then that, if we’re talking about a proposed habitual behavior toward strangers, what matters is not just if anyone is fine with it but what the odds are that over several goes, it will be hurtful to some people?

Well that’s why I commented in the first place, because I saw that there were many people reacting negatively to what the OP is doing, and I personally would not, but once the general consensus starts to form on a post like this it becomes difficult to voice a dissenting opinion. I feel that it’s worthwhile then for me to share my feelings so if others feel the same as me they can either upvote my comment or feel more comfortable adding their own, so the OP has a fuller range of opinions to work with. I think regardless, if this many people are bothered by it then the OP should seriously consider whether continuing to do what they are doing is the right choice.

I think the part about you potentially being put in danger is a pretty important distinction! In fact, I think it’s pretty difficult to abstract away from that fact. Let me know if another analogy occurs to you.

You could use kinks as another analogy I suppose. Like, if I want to have sex in a specific way that may not be comfortable for the other party, obviously I should disclose that before we’ve committed to actually having sex. But if we aren’t going to have sex, then I think it’s entirely appropriate not to disclose that, because it isn’t relevant to the flirting itself. Or for a romantic example, if I expect certain things out of a relationship, like that we are in that relationship long-term or that we go on a certain number of dates a week or something, that’s not something that is necessary to disclose until it’s actually relevant, and if there is no intention of ever pursuing a romantic relationship, then I think never bringing it up isn’t wrong.

I’m sure you have already come to the conclusion that our perspectives are wildly different and quite difficult to reconcile owing at least in part to our different experiences (statistically, you’ve been hit on more in a ~2 year period than I have in my whole life, based on your other comment), but I hope that you can understand why someone deliberately misleading me to milk some compliments out of me for the sake of their “need”* for validation while not having the slightest possibility of any genuine interest in me at any point might not actually be a super validating experience for me. Someone condescending to telling me what they think I want to hear so that I express interest in them and they feel good about themselves does not appeal to me.

Well, I did mention that people started flirting with me a lot more after transitioning. I’m familiar with the feeling of basically never being flirted with and going many years without a romantic relationship. And sorry, but I don’t think the OP’s behavior would have bothered me then either.

But really more what I’m struggling to understand is why people here are seeing flirting without a desire to take that further as not genuine interest. You seem to be assuming that if they flirt with you because they want to be flirted with in return, that they don’t mean what they are saying, but I don’t think that is necessarily true. Whether or not I’m intending to pursue a relationship with someone, I would not flirt with them if I didn’t mean it. When you say they do not have the slightest possibility of any genuine interest in you, that they are deceiving you, that they are telling you what you want to hear to milk compliments out of you and so you express interest in them, it reveals that:

1. You don’t think it’s possible for someone to mean what they say when they flirt if they don’t follow through with their flirting, which isn’t true.

2. That flirting and being flirted with because it feels good is not a sufficient reason to flirt, and that they must commit beyond that. You have an expectation that if you and someone else are flirting that they will necessarily want to date you and/or have sex with you, or even that they are obligated to. Consider how obviously wrong this line of thinking would be if you remove the sexual aspect from this. If you were to get mad at someone for joking with you at the bus stop but then revealing they do not want to be your friend, that would obviously be ridiculous.

I’m not saying you aren’t allowed to have hurt feelings if someone did what the OP does to you. But I think this way of thinking about flirting is unhealthy, and I don’t think it’s the OP’s responsibility to manage that for others. If they want to stop anyways because of it, that’s understandable, but it isn’t enough to convince me that what they are doing is actually wrong.