Would you ever date....? Why/Why not?

1. Your friend's/sibling's ex
2. Your friend's sibling
3. Your childhood friend
4. Your boss/subordinate
5. Your sibling's friend/classmate

I know some of this happens a lot in mangas but I imagine it might be more awkward irl idk- And no I'm not putting teacher/student because that's just.... no.

My answer:
1. This is a dilemma I'm facing atm. My friend went out with this guy for a couple months last year and they broke up peacefully. They found out they were too similar and decided to just stay as friends. (If the break-up was horrible/if the other party treats my friend badly it's a definite no). I'm starting to like the guy but it's still weird?? I keep thinking, "STOP liking him he's your friend's ex ffs"

2. Yes. It'll be awkward but wouldn't be the worst thing in the world.

3. Honestly no. They're practically siblings that I can't see them romantically and/or sexually.

4. No. I'm sure some people can make it work but I personally don't think I would. Conflict of interest.

5. Same answer as number 2.