Tbh, he should sweat a little bit. Romantically speaking, he's been relying on having a pretty face and telling her he's really nifty. Her relationship with the guildmaster is transactional, and her relationship with his real face explicitly serves a utility purpose. If he wants anything real he's going to have to just. Talk to her. No scheming, no lies, no trying to manipulate her into seeing him in a better light. Just "hey, those two guys you've been talking to are actually one guy, and I like you". Anything else won't move things forward.