Just because he has a guitar and is a singer, doesn't make him a sensitive guy.
At some point during the 1990s, it became not just OK but almost preferred to be a sensitive dude, in the estimation of women. "Soulful poets" like Kurt Cobain made the ladies swoon with enlightened ennui. Adam Duritz (of Soul Asylum or Counting Crows or Third Eye Blind) may have bedded every woman in Hollywood (and beyond, but particularly the female cast of Friends). Read All About Jennifer Aniston
While owning a guitar and knowing how to play a single chord (or whatever it's called) has always been a good way to land ladies (it has really worked out for Oasis), the 90s brought very good tidings for the sensitive man. Flannel shirts, messy hair (particularly anything that could be described as "nappy") and goatees were somehows signs that a dude had a feminine side and therefore knew how to make a gal feel special. All he had to do was insert her name into a song and that was it all she wrote. (Note: a homey from way back once tried calling a beautiful night a "Lisa night" to a gal named Lisa, there was no shooping as a result of that silliness.) John Mayer is still living this Ethan Hawke-esque dream.
Along the way, some dudes did actualy become sensitive and artistic and all that jazz, but the rest of the guys were just going through the motions because the plan was ingenious. All he had to do was not shave, wear baggy clothes, learn a few guitar chords, just tell his guys friends that he was a warrior poet* and it was all gravy. (Unfortunately, the plan was not as successful as it could have been because everyone was skittish due to Magic Johnson catching the HIV.)
Unfortunately, this sensitive 90s guy gig hasn't gone away. While a lot of guys choose to embrace their sensitive side by engaging in bromance, some dudes are still taking care of business by being sticking to the sad bastard routine. In the first episode of Flight Of The Conchords, Dave sulks at his own party because chicks dig it.
We need to put an end to this weltschmerz-as-game once and for all (I'm not hating the player, I am hating the game). Our buddies over at College Humor epitomize the movement in a very funny video called "Sensitive Love Ballad," I highly recommend checking it out. The line about "how I read lots of poetry, like Sappho or Sylvia Plath, both of whom are girls," pretty much sums the whole thing up. Together, we can put an end to fake sensitivity in our time. Yes we can.
*Note: Despite having a Chinese symbol for it, there is no such thing as a warrior poet, sorry.