Forgiveness is easier than permission
As a general rule you should lead your life boldly doing what you think you should do, without asking permission to do it. It’s great to talk things through with friends, to get second opinions. To get a sanity check, so to speak.
But a lot of the good things in life come from acting spontaneously, yet appropriately. You’ll have a much wider freedom in which to act if you remember the simple principle that forgiveness is easier than permission.
In other words, if you want to take the girlfriend skinny dipping, take her skinny dipping… or if you want to surprise the wife with a vacation, surprise her with a vacation.
Just take smart risks and don’t be afraid to fail.