hehehe... here’s a preemptive warning for anyone who hasn’t read the manga because my answer involves major spoilers! though I’ve probably already spoiled a bunch of stuff just with my tweets... alas...

me and my best friend figured this out yesterday, but I think my ideal wv first kiss happens right before wolfwood dies, while him and vash are sharing a last drink. both of them are so very..... not the type to openly admit romantic feelings, so a first kiss is something I can only see happening right at the end. right after the “please don’t say anything stupid.” panel. wolfwood is the initiator— vash would not initiate a kiss in this scenario, no matter how sad he may be. these are wolfwood’s last moments and he doesn’t want him to go out feeling confused... or god... what if he doesn’t like it? and that’s the last emotion he’ll ever feel?? etc etc.... that’s too selfish. wolfwood ALSO kind of feels like an asshole for kissing vash and then immediately peacing out (because of something he did, too!), but hey, he’s the one dying here.... vash is understandably heartbroken about the whole situation but still treasures it. it’s a “I’m sorry I’m dying, I would’ve wanted to spend my tomorrows with you too, if things were different” without words. wolfwood made his decision and doesn’t regret it but it still sucks.