Honestly, yes - the flirty banter with Lae'zel and Shadowheart feels really odd considering how romantically shy Wyll is with the player character (particularly in Act 1, where I always heard that banter). It strikes me as an oversight that those banters can trigger even after your character kisses Wyll at the tiefling party. It's just so inconsistent with how he's portrayed in every other aspect of the romance.
Not to mention that he shuts down Lae'zel's advancement during the party and only has a chat with her. And we know Lae'zel is very straight forward with making clear what she wants, so it's not like he wouldn't have gotten the hint. To then flirt with her afterward is odd.
