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As the story progresses his relationship with various people in the guild does grow and evolve. I quite liked some of these. He also gets involved a bit more personally in some of the events.
But these are linear stories that play out automatically as the story progresses. There are no choices or multiple endings in this game.
That said, if you want, you can always head-canon that, e.g. the Guildmaster and Fiona have crazy hate sex after the final mission and get together. Or that the Guildmaster has a loving spouse that they left at home while all the crazy adventurer/bandit/demon stuff is going on, and just didn't mention it. Or that the GM has no interest in romance (or even just no interest in romance with the crazy folks who actually populate the guild).