Have you met Isabella? I don't know if that counts for it but I'd check it, or maybe get more hearts with Anna since it might be weird to kick him out when you're not that close with her. How far along are you with Anna?
Yeah, then it must've been that Anna's love was too low then, just give Josef a beer 3 times (3 weeks at fridays) and be mean to him, confess what you've been doing with Anna and he'll leave after that, there's another way of getting rid of him with Isabelle but that's up to you
For me I just gave Joseph a beer for maybe 2-3 consecutive Fridays and then the topic of Anna comes up and I chose the most disrespectful option they had.
