I’d go with Travis McGee. The book Travis, not the movie Travis.
A cool, caring guy with some really fascinating friends.
And hey, he lives on a houseboat!
Richard Jury, Melrose Plant
Phoebe Bouffet, Ross and Monica Geller, Joey Tribiani, Chandler Bing, Rachel Green
Joe from Zoom
J.D., Elliot, Turk, and Carla from Scrubs.
Jim and Pam from The Office.
Willow Rosenberg, Xander Harris, and Rupert Giles from Buffy the Vampire Slayer.
Jack Knight, the Shade, Blue Beetle II (RIP), Slam Bradley, Jake “Bobo” Bennetti, Wildcat, Catwoman, Elongated Man, Wesley Dodds, Dian Belmont, and Zatanna from DC Comics.
Dr. Peter Venkman and the rest of the Ghostbusters.
Well, considering that I’m a reasonably healthy heterosexual male, this is not an inconsiderable attraction.
Having said that, though - it’s more because I think he’s neat. I’ve got a fondness for trickster characters, and he’s perhaps the most restful trickster I can think of. It’s not that he’s above the usual flaws of the trickster, rather he’s less random in his effects than most tricksters.
He’s safer to be around than, say, Loki, or Coyote or even Bugs Bunny.
control-z, sorry. Patlabor is the title of a very well-done anime series.
If you don’t know who Miyazaki is, or look down on the idea of animated films for grown ups, go out and rent Spirited Away . Now. 
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Rebecca Davitch - Back When We Were Grownups by Ann Tyler. She does so much and no one even appreciates it.
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Alianne of Pirates Swoop - Trickster’s Choice by Tamora Pierce.
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The entire cast of The Enchanted Forest Chronicles by Patricia C. Wrede.
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Auron - Final Fantasy X. But only if by “be friends with” you mean “violently rape”.
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Riccardo Belli - Demento/Haunting Ground.
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Jared, the Goblin King - Labyrinth. See #4.
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Luna Lovegood - Harry Potter and the Order of the Phoenix by J.K. Rowling.
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Mr. Rohchester - Jane Eyre by Charlotte Brontë. Again, see #4.
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Nymphadora Tonks - Harry Potter and the Order of the Phoenix by J.K. Rowling.
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Madmartigan - Willow. So schmexy.
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Indiana Jones - Indiana Jones and the ______.
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Amélie Poulain - Amélie.
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Heathcliff - Wuthering Heights by Emily Brontë. See #4.
Okay, now I’m even more confused. I’m familiar with the notion of the trickster character, but how do you see Tenzil as fitting that role? Has he changed post-Crisis? (Pre-crisis he had little personality, and the most significant things I can remember him doing are eating the Miracle Machine and outsmarting a super-strong bismollian by eating through a flagpost).
I’m not being a smart-ass; I’m interested, really.
Well, I’m mostly familiar with Tenzil from the stint that Tom and Mary Bierbaum did on the comic (LSH Vol 4). During that he struck me as a trickster, often forced into that role by virtue of the people he choose to challenge, but also in the sense of the team joker, too. If you never read it, you should look up the issue where Tenzil goes to earth to rescue Polar Boy from Earthgov. His attempt to cop an insanity plea for Polar Boy was fricken hilarious. Certainly I liked the story where he freed Saturn Queen from her husband Evillo’s thrall. (Along with more than a few other people…)
I dunno about Miles. He’s likeable enough, but most of his friends have a horrible habit of ending up hurt, maimed, or dead. I could see partying it up with Ivan when he was in town though…
Mary Crawford from Mansfield Park. Sure, not a moral scruple to be seen but she’d be fun to hang out with. Maybe we could collect Becky Sharp in our fabulous literary time machine and see who was more of a conniving but intelligent dame. Ooh. And Lady Glencora Palliser and her good friend Madame Max who has more brains but slightly less charm than Lady Glen. Not that she doesn’t have charm, but Lady Glen is just so over the top.
My favourite is when he’s at the archaeological explidition that dug up the Batcave, and called the giant penny proof that gigantic presidents once roamed the galaxy. (He thought it was a manhole cover and scaled up the people from that…imagine how big the Titan Presidents of Bismol would have been if he’d realised it was a coin!)
My Legionnaire-friends-of-choice: Tenz, Chuck, post-Emerald Vi post-ZH Shrinking Violet, post-ZH Dream Girl.
Well, safety isn’t exactly the top priority on my list. You’re talking to the person who put Tenzil Kem on his list as an allegedly safe companion. I’ll take my chances around Miles. Besides, it’s safer being his friend than his enemy. 
Richie Rich. Who wouldn’t want to be friends with the richest boy in the world?
Two that immediately spring to mind are George Smiley and Arkady Renko.
They’re both smart (Smiley abnormally so), and they seem like they’d be pretty undemanding. They wouldn’t try to pry too hard into your life, and they’d probably be rather tolerant of your idiosyncracies, since both are unusual enough in their own right.
I’ve got a thing for quiet, unassuming people who nevertheless manage to crack the case or save their country. Smiley and Renko are probably my two favorite fictional characters overall.
Nanny Og - as a drinking buddy and general baud
Havelock Vetenari - as an advisor
Cohen the Barbarian - as an enforcer
Kaylee Frye - as a friend with privileges
Most of?There’s Illyan, but that wasn’t Miles’ fault.
There’s Bothari, who had it coming and who could have stopped it but didn’t.
My own choices:
Credeiki from Startide Rising would be interesting, on his own merits as well as the smartest sentient dolphin around.
Wiz Zumwalt from Rick Cook’s Wizardry books seems like a stand-up guy.
Lupe dy Cazaril from The Curse of Chalion would be a good man to know, and very handy in a tight spot.
Andrew Hale from Declare always struck me as a man in need of a few good friends.
Brendan Doyle from The Anubis Gates for the same reason.
I’d say Janet from Tam Lin, but a) my motives are not entirely aboveboard, and b) I probably can’t compete with her current boyfriend
In no particular order:
Samwise Gamgee
Tom Sawyer and Huck Finn, both
Odysseus
Catherine Montaigne, from the Honor Harrington books
Ellie Arrowway, from Contact
Manuel O’Kelly Davis, from The Moon is a Harsh Mistress. Also Mycroft, of course.
Dr. Susan Calvin, of Asimov’s robot stories. OK, so I also have a major crush on her, but I’d be willing to settle for “just friends”.
Charles Wallace Murray, from A Wrinkle in Time and sequels
Jimmy the Hand, from the Riftwar books by Raymond E. Feist
Xander, definitely, But Willow? Too evil.
Gort. (From ‘The Day The Earth Stood Still’). A pretty good ‘friend’ to have around. Any problems and… zaaaaap!!!
All three of the Three Men In A Boat. They’d be great company.
Julie in ‘Day For Night’. Or Cathy in ‘Bullitt’. Or Paula in ‘The Mephisto Waltz’. Or Gail in ‘The Deep’. In other words, someone who looked exactly like Jacqueline Bisset. I know not how to wish for more.
I think the android Data, from “Star Trek: The Next Generation,” would be a fascinating person to have as a friend. Hmmm, maybe even a “friend with benefits.” Gotta check out that “fully functional” claim of his.
Hey, if you want to break them up, I’ll make a play for Thomas and then it’ll be easy sailing for you to get to Janet.
My own literary best friend is Philippa from the Lymond Chronicles. I have something like a 4th grade friend crush on her … I just know that if we ever met, we’d be official Best Friends Forever. We could write BF4EVER!!! on all our notebooks. Or something.
The other fictional guy I want to be friends with is Cuthbert from The Dark Tower series. This predates the middle book in the set, so back when Cuthbert maybe had four paragraphs total in three books. This perplexed Mr. Del to no end. He’s not even really in the book! I don’t care, I just know we would be friends. I like his style and his offbeat sense of humor. Also, he can’t possibly end up worse with me as a friend rather than Roland.