Is it not a good idea for the guy to flirt with her in this situation?

Anonymous
The girl had previously been on a few dates with the guy and then the girl told him she enjoy his company but more as friends. And then he said he’d find it difficult to be friends as he finds her attractive so they parted ways as she suggested that’s probably what’s best for now. She also said it’s bad timing for her. But then after 6 months she liked his instagram post so he got in touch and he asks her to a walk and then an exhibit and then a candle light concert. In this situation, is it a bad idea for the guy to flirt with her?
It’s a bad idea for him to flirt with her
It’s fine for him to flirt with her and test the waters
Select gender and age to cast your vote:
Is it not a good idea for the guy to flirt with her in this situation?
2 Opinion