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[Jewelie]

Just to check, who does it direct you to talk to first? I'm not sure if this is the case for everyone, but in my experience the one you have the romance option with is always the second one it directs you to talk to, and you never get the option to romance the first person (presumably because the game wants to allow you to talk to both, and the romance option goes overnight).

At least for me, for the first person I talk to (determined by which quest pops up first), the only final dialog option is to affirm the friendship. Based on my experience which triggers first was determined in that temple conversation (I've never been woken by Calia, thanks for telling me about that!).

I know you weren't hoping for Calia on this playthrough, but have you checked to see if the romance option comes up with her? Personally I think both are really well-written and compelling, so if you were planning on seeing all the content anyway, it might save you some time to finish this game with Calia and romance Jespar on your next playthrough.

On the airship, Calia was the first to talk to me and I reaffirmed her friendship (99% sure). Second one was Jespar (which I could also only reaffirm friendship with). Maybe I could try the console command with her and play out the romance that way? Hmm... Judging by the way it didn't work with Jespar, I don't think it will work with her romance but I can try. So in your temple conversation about feelings you were woken up by Jespar? That may be key...

[Cassiopeia]

If you talk to Calia first you probably don't have the option to romance her, either, at least not without backtracking a bunch. I was woken by Jespar in the temple, but I don't think that's the determining factor because that's been the case even on playthroughs when I romanced Calia.

Sorry, I'm stumped

[Jewelie]

This is from a good while ago, but I figured it out. Before going to sleep in the Temple (when you are woken up by the companion you have the highest affinity with/are romancing), I put in the console commands to increase Jespar's sympathy and flirt meter for me, and lo and behold, he woke me up. I finished the game, successfully playing his romance, with only a little backtracking. Thank you to everyone for your help, I think my next playthrough I'll take a different route, as much as I love Jespar.

[Toft]

This may be an entire red herring, but there was one unusual conversation (as in: i only stumbled upon in once in all of my 7 or so 'play-thr...'s (i.e. i think i may have got to an ending once)) and, of course i cannot remember exactly when it occurred. (Any clue would be appreciated).

I think it was before that bit where Jespar gets all antsi with you and flounces off in a Big Purple Huff. The thing i definitely remember is J getting flattered, yet uncomfortable, and basically responding with a response of "Enough with all the sex talk already! Don't rush me!" (Exact quotation not guaranteed).

Any recognition/ideas?

[Jewelie]

This may be an entire red herring, but there was one unusual conversation (as in: i only stumbled upon in once in all of my 7 or so 'play-thr...'s (i.e. i think i may have got to an ending once)) and, of course i cannot remember exactly when it occurred. (Any clue would be appreciated).

I think it was before that bit where Jespar gets all antsi with you and flounces off in a Big Purple Huff. The thing i definitely remember is J getting flattered, yet uncomfortable, and basically responding with a response of "Enough with all the sex talk already! Don't rush me!" (Exact quotation not guaranteed).

Any recognition/ideas?

The only thing I can think of is the talk in the Watchtower where you can highkey flirt with Jespar and he'll chastise you but I can't remember exactly and that quest is closer to the beginning of the game. Either my memory is failing or I didn't experience that occurrence, sorry!