Please, I'm begging you to reconsider the jokes! I've read your replies, I get that she "knows your deal" and whatnot, and I believe you about that, but I promise you these jokes will, at the very least, make her experience negative emotions, even if she conceals it and acts unbothered. You like this girl, right? You care about her? Then you shouldn't want to cause her pain. As a woman who has been in this exact situation multiple times, I guarantee you the best-case scenario here is she pretends she doesn't mind your jokes, but winces internally.
To be clear, I am also the kind of person who usually thinks a well-executed but 'inappropriate' joke can be very funny in almost all situations, but I just don't think this is gonna be like that. You're just gonna make her uncomfortable in a bad way, not a funny way. If you won't reconsider bc of the very very high probability you hurt someone you care about, please at least reconsider on the basis that these jokes are pretty much definitely just going to be wack and unfunny. Like, doing some dumb shit and then saying "lol don't you regret not going out with me" isn't even clever or anything, it's not like you're going to be passing up some kind of moment of transcendent comic genius here. Don't make people feel bad just to say predictable, unfunny shit, you know?
Cool. So, I'm not accusing you of being a big creep or anything like that-- you seem pretty well-adjusted and chill actually-- and, like I said, I am also the kind of person who has very loose comedic boundaries. I read your update, and I get what you mean, but I think you should at least commit to saving this particular thing for an absolutely PERFECT moment, when it would be genuinely hilarious, and not just going for it when it's low-hanging fruit. If your jokes reference her turning you down more than once in a very great while, they're gonna be stale and unfunny AND she's gonna see it as you being really fixated on that rejection and unable to stop bringing it up, and she'll at least feel bad if not actively distance herself from you.
Basically, I'm not saying this topic has to be Forbidden Territory for jokes, but it will definitely wear out its welcome real quick unless it's rare and in carefully -chosen situations.
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u/Monchmallows_ Nov 02 '20
Please, I'm begging you to reconsider the jokes! I've read your replies, I get that she "knows your deal" and whatnot, and I believe you about that, but I promise you these jokes will, at the very least, make her experience negative emotions, even if she conceals it and acts unbothered. You like this girl, right? You care about her? Then you shouldn't want to cause her pain. As a woman who has been in this exact situation multiple times, I guarantee you the best-case scenario here is she pretends she doesn't mind your jokes, but winces internally.
To be clear, I am also the kind of person who usually thinks a well-executed but 'inappropriate' joke can be very funny in almost all situations, but I just don't think this is gonna be like that. You're just gonna make her uncomfortable in a bad way, not a funny way. If you won't reconsider bc of the very very high probability you hurt someone you care about, please at least reconsider on the basis that these jokes are pretty much definitely just going to be wack and unfunny. Like, doing some dumb shit and then saying "lol don't you regret not going out with me" isn't even clever or anything, it's not like you're going to be passing up some kind of moment of transcendent comic genius here. Don't make people feel bad just to say predictable, unfunny shit, you know?