There were at least 4 Thanatos/Hypnos conversations to get through, and a few conversations with Dusa and Hades in the middle of all that. Also, make sure to buy the tombs cosmetic I mentioned, as it was mentioned by Dusa in one of their conversations. If not, talk to him solo and then rinse and repeat. Then, hopefully he'll be talking to Hypnos.

If you don't care about winstreaks or anything like that, the best thing you can do is start a run, wait until you get Thanatos to appear (likely, but not guaranteed), and then get yourself killed in the room after. It really was just a matter of Than having a huge backlog of things to say (including incredibly minor things, like random comments about Sisyphus or Orpheus. That said, I otherwise am satisfied with everything I've done in this game.ĮDIT: (In case anyone having the same issue finds this later) I eventually got it. If I don't figure out what I'm missing, I'm throwing in the towel and shelving the game for now until a more concrete answer is discovered.

The most common advice is to simply 'keep playing' until the dialogue occurs, but I genuinely have not received a new dialogue from Hypnos since my early hours of playing, which is several dozen runs ago at this point.

I added the tombs and completed runs since, but still have not seen any progress in that area.

Purchasing the tombs cosmetic in the great hall, as I've read that apparently affects him somehow.

The quest is apparently about improving Hypnos' work ethic, but as of their last conversation Hypnos is as lazy as ever. I have completed Thanatos' romance and any other quest in which he was involved, but he almost never appears to talk to him, only once in several dozen runs. The few things I have read that involve unlocking the quest are: I've tried looking it up on this subreddit and elsewhere, and no one seems to really know for sure what triggers it. No matter what I do, I can't make any progress to unlocking the sleepy boy's heart.

After lots of grinding, I did all of that. The credits, the epilogue, Extreme Measures 4, unlocked the hidden aspects, and maxed out every character bond.

So I have more or less completed all my goals for Hades.

Download free hypnos hades