I Am and Will Always be a Sucker for Guys like Jake Barnes, Nick Carraway and Holden Caulfield

First, the guys

Jake Barnes

• “You can’t get away from yourself by moving from one place to another.” (understands running is not a way to solve problems)
• "'Nobody ever lives their life all the way up except bull-fighters.'" (knows that unless we have a job that puts our lives on the line on a daily basis, literally, we don't truly live)
• "This was Brett that I had felt like crying about. Then I thought of her walking up the street and stepping into the car, as I had last seen her, and of course in a little while I felt like hell again. It is awfully easy to be hard-boiled about everything in the daytime, but at night is another thing." (knows how to love and write about love and feel love, also honest about his feelings)
• "I was a little ashamed, and regretted that I was such a rotten Catholic, but realized there was nothing I could do about it, at least for a while, and maybe never, but that anyway it was a grand religion, and I only wished I felt religious and maybe I would the next time...." (fights with his spiritual self and sometimes his not so spiritual wins, how human)
• "Enjoying living was learning to get your money's worth and knowing when you had it." (learns how to enjoy the life he's been given)

Nick Carraway

• "Every one suspects himself of at least one of the cardinal virtues, and this is mine: I am one of the few honest people that I have ever known." (understands the aspects of him that have virtue)
• "There was no difference between men, in intelligence or race" (neither racist nor elitist) 
• "They're a rotten crowd," I shouted across the lawn. "You're worth the whole damn bunch put together." (understands what it means to be a true friend)

Holden Caulfield

• “Certain things, they should stay the way they are. You ought to be able to stick them in one of those big glass cases and just leave them alone.” (understands that there are things that should remain constant, also understands that not everything should remain constant)
• “People always clap for the wrong things.” (not interested in being shallow)
• “I don’t give a damn, except that I get bored sometimes when people tell me to act my age. Sometimes I act a lot older than I am - I really do - but people never notice it. People never notice anything.” (knows that people don't always notice the right things, also realistic)

Why I Love Them

1. Honesty: while they may not be the most upright of men (OK, I get it Holden isn't really a man, but the first time I read that book he and I were the same age, so I feel like we're still the same age...whatever), they are in fact quite honest about that. They do what they know to be right, even if the world may not think that's what they should be doing.
2. Intelligence: all three narrate their own stories and so we can a sense of their thought processes and what thought processes they are. We learn about phony people, what they value in their fellow men and in women, we learn who they are and we learn that they have a code and honor and a sense of what is right and wrong, even if they don't always know or care to know how to fix it.
3. Challenging: all three of these guys are tough nuts...who will keep any gal on their toes and I like that. I like the idea of being the person who can not only see past that hard shell, but also be the one that does the cracking...they may not be the best listeners, but isn't helping them learn how to be part of the challenge?
4. Manliness (yes, even Holden Caulfield): in the way they talk, what they say, how they act, who they associate with...sigh...
5. Naivete (yes, even Jake Barnes): even the strongest, toughest man has a place in his mind and heart that still acts and reacts as a boy. Each one of these guys has that part of him who hurts, doesn't mind crying and doesn't really understand the world. They are not hardened. 

Why It Will Never Work

Just in case you were wondering, no these traits don't translate over to real life very well. You see:

The Jakes are always out late, drinking and then want to philosophize with you forever about things not in your control or power to change. Then they self-loath for a minute and then...well, nothing.

The Nicks are runners and when they run, they run all the way home.

The Holdens are just as phony as they think everyone else is, only they'd rather talk to you ad nauseam about your faults and how you need to change. Oh, and they're also usually a little too young to be that cynical and mean.

I guess, I'll just stick to Chandler Bing...oh, wait...

And, then there's this little thing I found: Marry, Date, Dump?
My answer: Jake, Holden, Nick