Ah, that... He suggested it to my Tav and then immediately offered the poly arrangement in the evening. I guess in this order it's not so bad. It was still a very crappy moment because it happened right after getting all the answers right with Astarion during the love test. Both of them sweet and happy together, kissing, etc. And then Halsin was like... 'Oooh... I like it. I wanna get in there too.' Left a bad taste for sure.
This made me laugh because I too associate Halsin most of all with very bad timing. My Gale thought it wise to maybe tackle the whole Cazador situation with full spellslots. So, while his dearest vampire was in pre-Cazador-panic, Halsin thought it was a good idea to propose his arrangement - I hope Astarion had a good laugh, at least. (I still think it's a shame you cannot get Astarion's conversation after saying no to Halsin) Then, the next morning, Mizora comes up with her suggestion .... I imagined Gale telling her to go see Halsin and then trying his best to never think about this particular series of events again. Even the game itself enjoys teasing Gale at every opportunity!
*coughs* Back to Wyll.
Edit: And he chimes in, showing interest pretty early with the Drow, while the player still has all the clueless text options.