Put on some sad music to set the mood before continuing:

Aww.

From the article:

The October letter marked at least the fourth time Mr. Obama has written Iran’s most powerful political and religious leader since taking office in 2009 and pledging to engage with Tehran’s Islamist government.
[…]
Mr. Khamenei never directly responded to the overtures, according to U.S. officials.

Double aww.

The mixture of mockery and embarrassment is something to behold:

Copies of the actual letters aren’t available, but it can’t hurt to speculate as to their contents:

Update:

This is probably one of the more accurate guesses: