He says I remind him of his daughter BUT he also flirts???

Help me out here. He says that I remind him of his daughter, (who is older than me). He split up with his partner some time back so she’s not in the picture. After leaving the office, he stares at me whilst closing the door. After I say goodbye on Fridays he stand back and makes eye contact for a good few seconds. He has said so many flirtatious things which make me believe he likes me in that way, however when he says I remind him of his daughter it makes me think maybe he sees me as a daughter figure? All I know is that we are very close and we have known each other for 3 years. I’m doing a degree in university and for a joke I told him I was dropping out and immediately his eyes filled with tears. I do have feelings for him and perhaps he has picked that up, but I’m unsure where we stand. He keeps on that he’s a professional considering he’s my manager, but today I joked about his professionalism and he said “I do try to be professional but i usually fail”... what does he mean? I can apply it to our situation; flirting, intimate discussions and disclosing personal information... so possibly he was talking about us. I want some feedback please.