If you flirt with an NPC or a dragon… You’re making the DM either very uncomfortable, or you are turning him/her on.

If the DM asks you you really want to do something look at their expression and do it anyway.

If you want to do something really stupid, crazy or narrativly disruptive look towards your fellow players to get their consent. Then do it.

The time to argue technicalities is outside of sessions to not waste precious gametime. Do it during sessions only if you are into that weird shit.

The best way to get to use new character options is through DM bribes. In this case a sourcebook is recommended.

If you help clean up afterwards you may get inspiration.

Also

Snacks are an acceptable bribe