So, when I got the weave scene, I failed the 2nd roll to speak the magic words, thereby ending the encounter prematurely. I heard that the only way to start/trigger his romance route is by passing both the checks and then choosing to either imagine kissing him or a romantic walk.
But after the weave lesson ended, I had a new dialogue option with him, and I wonder if this will also triggers the romance? It certainly did seem flirty:
https://imgur.com/a/EioIEWB(Incidentally, I'm totally pulling Gale aside for a "alone moment" to bite him after this -- he doesn't know yet)
Would love if someone can confirm/deny if this is the case, or if I need to reload to re-do it.