impossible or possible relationship??

So I broke up with my boy friend a month or two ago. I waited until now to start listening to my feelings and checking out guys again. The guy that I really like is my ex boyfriends best friend, and he broke up with one of my close friends 4 months ago. I really like him, he is super athletic and smart and has a great personality. I can really see a future with him, and I really want to try and start flirting, but I don’t know if I can. His ex doesn’t care if I get in a relationship with him, i’m not sure about my ex tho.

Is it too early to start flirting?

Is it a bad idea to date him due to his ties to my ex and friend?

Should I try and pick a less tricky situation?

Should I give up??