Hey there! So in chapter 2, the tower starts having issues. While Mason is fixing things up, you can take some of your employees out on dates, to see if they might still be wanting something. Usually 2 dates will give you an idea of something they want, and you'll get a 'think about X's problem' prompt in your room. You can romance them yourself, if you're both available, or hook them up with one other potential employee, if you want to play match maker (The other employee will also need to be taken on a few excursions, to find out what they want)
I'm going to say you can date multiple at once, many of them don't mind being part of a larger group. To me that's a harem. However, people get very particular about their terms, so I'll add the game doesn't assume their only romantic partner is you (They're heavily implied to get with each other as an extended family unit, and many continue doing their thing with others on their own, though it's never a jealousy thing).
As the MC (Main Character), you can romance:
(Monogamous means is MC's only romantic partner, though not only sexual partner, and polyamorous means happy to be with other polyamorous romanced characters)
- Dana (Monogamous)
- Cass (Monogamous)
- Cassy (Polyamorous)
- JJ (Polyamorous)
- Petra - Siren (Polyamorous)
- Petra - Dark Elf (Polyamorous)
- Xun (Polyamorous)
- Sammy (Polyamorous)
- Samantha (Monogamous)
- Mason (Monogamous)
The following characters can be hooked up with another employee (and, of course, you can get frisky with them yourself), but cannot be
romanced by the MC:
- Xavier - Vampire
- Damien - Bull
- Jolie - Masked form
So let me know if something seems to be broken. Samantha has a slightly longer intro than the others (She was one of the first, when we hadn't nailed down the system). So for her, 2 dates in chapter 2. Then give it about 4-5 days. You'll get a message when you sleep for the night suggesting she seems down and you should try talking to her. After you chat with her, you'll have the normal 'think about her problem' prompt in the bedroom.
Note that Samantha is monogamous on her romantic path, so it won't be available to you if you complete (get to the 2nd date and romantically solve their problem) anyone else