With Wyll you only get the "dating with Wyll" flag if you were flirting with him at the tiefling/goblin party.
Did they fix that? Last time I played he wanted to dance with me even after I forgot about him at the party.
Nope. Wyll simply always wants a dance with you - unless the most recent hot-fixes changed this. I didn't forget him at the party but was very distant and polite.