2 problems that made it so I couldn't even get to the first date:

1) The pace is just. too. dang. slow. And by that I mean the rate at which anything happens. The text, the general pacing of the story, everything is too slow. Even clicking madly, it takes way too long to get through even a little bit of text and the intro is just bunch of pointless crap to slog through (thankfully I didn't ask for a recap of Helltaker, I can't imagine how bad that would have been), mostly related to point 2.

2) Rather than letting player actually, you know, play as the protagonist (like in the original game), the developers made the bizarre choice to have the entire thing be explicitly narrated to the player by the Helltaker in a fourth wall breaking fashion. There is absolutely no immersion. None. There is no connection to what's going on in the game. I don't need to see the Helltaker or have him speaking to me. I want to be the Helltaker. I want this to be a dating sim not a voyeur sim. Part of Helltaker's charm is that despite the limited interaction it feels like you can start to connect with the girls. And the reason players are going to look for games like this is to get more of that. Players won't feel like they're getting that experience if they're being treated like a third-wheel on the date, only there to give the Helltaker advice. That isn't what was advertised and it's not what player are likely to be looking for.

I could probably have dealt with one of these issues and toughed it out, especially the first. But all both? Nope. IT's sad, it's obvious, even from what little I saw, that there was a lot of thought and effort put in to this, but for all the polish they put on it, it's still a turd.