ok prepare for the yap of a lifetime:
gwylan’s interest is counted in two ways: the visible interest stat and their invisible progress points. I don’t remember how much each item gives in progress points, but iirc, the best are the soft bad ending ones, the temple stuff, the vintage clothing set, and the chain tunic set. Obtaining and showing Gwylan anything is still useful, but the ones I mentioned are the most important ones if you want to romance them.
The soft bad endings (that give you clothing) are the island, the prison, kylar’s mansion, the underground farm, the underground brothel, the asylum, eden’s cabin/the wolf cave (you only have to do one), and great hawk’s tower. They all have their own respective wiki pages with step by step guides of how to get in and out of them. I’m assuming you’ve been on the dol wiki before, but incase you haven’t, here’s the link:
There’s about a thousand temple items, so I’ll just explain a few of them. Temple monk/nun set: join the temple and get your grace all the way up and ask Jordan to get a higher rank. Pass the trial and you’re good. Temple confessor: once you’ve become a nun/monk, you can work the confession booth and… ahem… purge corruption.. once you’ve successfully purged for the first time you’ll meet the bishop and get the set! continuing with that one, once you’ve purged enough corruption (30 soft world) you’ll get the sexy temple set.
(I’ll try to be as spoiler free as possible with the next few since they’re a huge chunk of lore relevant to gwylan.) The vintage set can be obtained by showing the bleeding ward painting to winter at the museum. You can get this painting by going to a party with Wren and stealing it. You can meet Wren by sneaking into the docks, going to the cottage next to Remy’s manor, or going to prison. (I recommend to docks over the rest considering you can also get the catsuit from there.) The next time you visit the pub, Wren should invite you to go on the heist with them. You can get the chain tunic by showing Winter the hopeless cycle painting at the museum. (I personally think the hopeless cycle is a pain in the ass if you don’t go in with a very specific plan, so don’t get hooked on it if it’s too much lol.) You can get the painting by taking jobs on domus street till you get the key, then discovering the maze by robbing farmland manors. Once successfully navigating the maze, you should find the hopeless cycle painting! Bleeding ward is much easier since all you have to do is pretty much sit and read, but it’s all up to you whether you choose to do one or both :)
Once you’ve gotten interest high enough, you’ll find the forest shop’s ‘secret’ next time you enter. You can complete rituals with gwylan weekly to help purge corruption and grind stats like lust and yearning (which will appear as ‘+???’ until you unlock gwylan as a love interest.) Once you get interest high enough (again), gwylan will invite you to the cafe to talk about you and your experiences. afterwards you’ll hear them whisper to someone that “you’re ready”, and you’ll soon unlock the second ritual. Unfortunately, you have to fuck with gwylan’s boundaries to get them as a love interest. When doing the second ritual, you have to pass the physique check (I think I don’t remember which stat it is) to get on top of gwylan and give them a bigggg niceeee smooch. (I recommend doing they’re about to… climax… since it’s usually easier. They’ll get really mad and kick you out of the shop for a few days (I think it’s 3-5? I’m not too sure.) You can find them sulking at the pub a couple days later in which they’ll get a little freaked out before leaving once again. Once the days have passed, you’ll get a letter from gwylan at the orphanage apologizing for throwing a fit and inviting you to come back. Once yearning hits around 50%, they should take you for a day out and you’ll unlock them as a love interest. (If this scene still doesn’t trigger after a few days, you might need to get a few more interest points or mess around with their other stats.) You can also get the familiar collar with high lust, high interest, (85% or higher), and yearning at around 80%.
An extra thing I wanted to add is that gwylan gives some interesting dialogue when showing the mask set (the islander and fox mask.) You can get the fox mask by letting Avery win their card date (4th date), in which they’ll invite you to an elite party where you’ll unlock the mask. Something interesting also happens when you refresh the page when Gwylan talks about the two masks, though I’d recommend saving before doing so for… reasons.
This was supposed to only be a few small tips regarding how their stats work, but I got sucked in so I’m sorry for the infodump 😭 If you have questions about anything else lmk! 🫶