Anyway, I'm not saying friends dating each other's past dates is something to strive for, but it's also ridiculous to pretend it never, ever, ever happens...no? As long as all parties communicate/double-check, have completely moved on, and are comfortable with it, I don't see the issue. Furthermore, I even suggested that Kelly could have approached Issa about it first, which would have allowed for a wtf-hell-no if the writers saw fit. I truly believe they could have written it to play out in a tasteful manner tho.

I once set up a friend with a guy I'd hung out with a couple of times years prior (prob most similar to Issa and Nathan's vibe). We did not consider each other exes, and it wasn't a big deal.... There was zero chance of attraction resurfacing, I had since entered a relationship with a diff guy my friend had herself set me up with, and I was actually out with her when Nathan-guy noticed her and asked me about her in the first place.

He even went out of his way to call me later that week to press further for her info, and at that time I personally knew that she was not only bummed about being single but trapped in a toxic cycle of falling for taken men. I was more than happy to link her with a vetted, actually single, and normal 6'5 dude with an MBA, and she was intrigued enough that she approved me passing on her info in spite of me meeting him first like 2 years before that. Should I have blocked a potential love connection for no reason? lol. Literally nobody cared.

Issa never loved Nathan; I think with the right timing it would've been fine *shrug*