Are Transgender "Admirer's" Gay?

This is an unintended follow up post to DeAnna's comment about transitioning from a gay man to a transgender woman.
On a different slant, the argument has raged on both sides of the fence about a man's sexuality if indeed he is attracted to you as a trans woman?  Is he indeed gay and if so, who cares?  I guess many do indeed care.
For what it's worth, I have two definitions.  The first is a straight (no pun intended) forward "Yes he is gay, if he is attracted sexually to another man, no matter how he looks."  The second (and the one I believe in), no he is not gay because the transgender women he is with, in no way considers herself male.

Fortunately, for all of you, I have another idea on the matter from this video on the Cyrsti's Condo big screen: