stuck in the miry clay

i'm labelled as an "eternal optimist".
a friend recently asked me whether i rely on my heart more or my mind more when it comes to relationships, and i think, without a doubt, i answered "heart". i'm not the most rational of people...kind of an irony because i love to overthink.
i've been contemplating the phrase "if you love something, let it go"...how true is that? lately, i've been finding myself "letting go" of certain things/people that I love...which is actually something that's very very difficult for me. (refer to me being the eternal optimist) i've been making an effort at it because i have this fear that these people/things will eventually disappoint me...therefore i should "lighten the load", so to speak, off myself. to love something doesn't mean possessing it...and yet another part pulls at me, telling me to make a better effort...to not give up the fight even if it means scarring myself hard. is love letting go or rather, is it a fearless abandonment of all the embarrassing and scary things that might happen if you keep at it?

(not necessarily a rhetorical question...answer if you'd like)

p.s watched ron sexsmith perform on some talk show (vicki gabereau..i think) and was completely astonished. he was just so beautiful singing to his piano-playing...it really captivated me. might run out to buy the album.