On a scale of “feasible with some minor dismemberment” to “Will require too many respawns to be worth it” are the Witherborn boys dateable as a human?
Depends entirely on who you're talking about!
Really depends on just how devoted you are to them, because they do remember scents and SOUL frequencies, so they'll know it's you.
Classic is probably "run for your life a couple times but you'll get away mostly without injury"
Red is probably "yeah you could do it- just expected to be attacked a couple times (I hope you have netherite gear and some pretty damn strong shields and God Apples if you want to live though)"
Dust is very likely closer to the whole "you will die several times, but eventually he'll just get tired of it and let you hang around (aka, he likes you)"
Nightmare, though, is very near the edge of "Will require too many respawns to be worth it."
So is Error and also likely Killer, but everyone's worth it if you hang around for long enough.
Feel free to ask more specifics on other Sanses if you wish :]