Hydaelyn Role-Players

Yes, during major character deaths.
Usually I disapprove of the use of infanticide in RP since it usually follows with intense grimdark, though this was pretty well executed.
Essentially, our FC had a mascot babby that everyone adored (possibly due to maternal/paternal envy ICly). Now..one of our members was taken along with the kid, and so everyone deployed on their merry way to rescue the two, and we had a jolly time doing so! There were laughs, the occasional corpse, a few 'WHY WON'T YOU DIE ALREADY' moments..aaand then we realise at the end of all the chaos, babby didn't make it.
The sudden realisation hit us IC and OOC, and sent everyone spiralling into 'ooooh no..' moments.
Suffice it to say, someone was taking layers off of Shrek next to each of our members at their desks.

Honestly, I don't think I have. I mean I've been in some tear jerkers but they've never IRL punched me in the feels.

I haven't had a sad RP on FFXIV in my time on it quite yet. Not one that made me cry anyway, but I can tell you about the first time I did cry in a roleplay situation.

I was at a LARP some time back and playing as a staff NPC during the big end of weekend event (we went in-character 24 hours a day for 3 days straight at each event with no soft-stop on activities so that night owls could have events in the dead of night). The whole in game town had been fighting off invaders during the day and undead during the night all weekend and were exhausted from it all.

Cue our NPC military detachment tromping into town. We were supposedly the good-guys, coming in to inspect the town and check in with the military unit of player characters assigned to the town. Our NPC leader met with the leaders of the town's unit (the commander of which being the game director's NPC and the Lieutenant being an actual paying player) in front of the whole town of player characters. The NPC in charge of our side spoke with the Lieutenant and asked to see an heirloom of the Lieutenant's...an old gun.

The NPC took the gun, complimented it, and then shot the Lieutenant dead with it in front of all in attendance. Cue massive battle. The aftermath of it I observed as a different nameless NPC and found myself in tears over all of the players who were distraught about the loss of one of the longest running and most well-liked player characters in game. (It had been the player's choice to retire the character)

I dont think crying over something that hit home is such a bad thing. Everyone has feels same as watching a movie and crying over it, because it touches you. I think if you do feel yourself welling up then the RP is successful specially since more raw and honest actions will come to the RP with how your character feels over the matter.