The following are the two snippets:

A1:

Doctor:Earlier you said you were afraid of something?
Me:Yes, I was afraid of seeing you in the eye.
Doctor:Are you sure that you are scared of seeing me the eye?
Me:I am very scared.
Doctor:You seem terrified by something.
Me:Your eyes.
This conversation goes fine with the doctor.

A2:

Me:I know your history.
Doctor:Possibly this is related to your plans?
Me:Very well guessed out !
Doctor:Why do you say very well guessed out?
Me:Stop fooling me.
Doctor:My secretary will send you a bill.

Now we'll see why this conversation failed.

"Very well guessed out !" was meant as an appreciation towards the doctor, but rather than thanking for that it replied with a question "Why do you say so ?" That was because the length of the statement was less than 9. So, according to the following code.

(defun doctor-huh ()
(cond ((< (length sent) 9) (doctor-type ($ huhlst)))

Doctor typed $huhlst which was nothing but $whysay + whatever the user sent

(let ((sent (doctor-readin)))

(make-local-variable 'huhlst)
(setq huhlst
'((($ whysay)(// sent) \?)


"$whysay" as per the following code pointed to "Why do you say"

(make-local-variable 'whysay)
(setq whysay
'((why do you say)
(what makes you believe)
(are you sure that)
(do you really think)
(what makes you think) ))

**************

"Stop fooling me" used here was meant to express irritation, the doctor took it as an instruction to stop the conversation.
The following snippet from Doctor's source code shows us why this happened. The statement contained the word "stop", so it was treated as a goodbye message by Doctor, in reply to which it typed the $bye message.

(memq (car sent)
'(bye halt break quit done exit goodbye
bye\, stop pause goodbye\, stop pause)))
(doctor-type ($ bye)))

(make-local-variable 'bye)
(setq bye
'((my secretary will send you a bill \.)