I don't think even the most pretentious of designers would ever scoff at the use of Comic Sans where it was appropriate and fitting, such as on the invitation to a 6 year old's birthday party. That's where is fits, it exudes 'fun'.
Where 'pretentious' designers do begin to huff is when it is used in a clearly inappropriately context such as on police notices raising awareness of rape.
The handwriting example isn't particularly good because learning calligraphy is a skill that I assume takes a decent amount of time to reach proficiency in. Making a couple of extra clicks in a word processor and selecting something like Arial is not.