If you just want to execute task by task and press OK for continuing you could use the step mode by adding --step to the ansible-playbook command.
This way ansible-playbook will ask before every task to execute it (=y) skip it (=n) or continue without stepping (=c).
Perform task: configure ssh (y/n/c):
$ ansible-playbook playbook.yml --step
However, - as Brian already pointed out - providing additional information during execution of the playbook is not supported.