The thing is with Dean Winchester is that he loves too much.
In fact he loves so much, that every second of his life is filled with all-consuming extremes.
He doesn't have many friends. Friends are time consuming, distracting, they remove your focus and cling on to you with ever increasing expectations.
Ner, he doesn't need friends, he prefers to surround himself with all those things he loves, they are his true friends, the only friends he ever needs, ever desires.

His first friend was Sam.
Some may argue that it was his father John, but nope, he was never a friend, he was his teacher, trainer, fucking soldier and sailor. Okay, maybe not a sailor, but with John Winchester you never quite knew. The guy was an anomaly in Dean's eye, a freakin' hero, someone to aspire too, but never quite a friend.

So yeah, Sammy was his first. (Oh God, could this even be any more gay? It sounds like Sammy took my God damn virginity, that son of a bitch) The most important thing in his life, the one thing that Dean cherished far above anything, even himself. (Oh please)
But Sam had grown, drifted away. Fair enough, he had come back, and throughout it all, Dean had never stopped loving, never stopped believing in his brother's greatness; even if he always did hide his feelings behind a heavy façade of bravado, extremities and wise cracks.
Sam Winchester would always be his conscious, that one part of compassion that sometimes Dean was lacking in himself. Sam saw in shades and grey, Dean not so much, he favoured his colour chart in black and white.
Sam is Dean's Jiminy Cricket! (Disney and Sam, that figures. Y'know i was once the Jiminy cricket to Sam's souless ass. Just thought i'd mention that)

Sometimes when he thinks real hard, which is something he tends to discourage, (Hey) Dean might even go as far as to say his first real friend was pie; his mom's pie which he was devouring before he even learnt to go to the toilet by himself. (T.M.I)
Pumpkin, apple, cherry, even blueberry, all delicious slices of heavenly goodness (pre Cas of course) that he couldn't ever get enough of. After Mary had died, pie was all he had left to remember her with. It was always evocative, always mom to have a warm, fruity slice laid out before him. Not that any pie ever quite lived up to his expectations, but it was home, it was a memory, it was mom. (Gulp)

Of course no one really understood his obsession with the stuff, least of all Sam who would often find himself getting bitched at yet again for failing to bring back a piece of good ole pie, or when he tried to substitute it with cake. (Yeah, cake; pfft…as if it could ever possibly come close! The jerk)

So maybe pie was his first friend? Let's put that one down as a tie.(Yeah, lets. That's a tough call)

The thing that people don't often understand about Dean Winchester is that he's far from stupid. (Humph) He's not book smart, okay that's a given, and it's not something he has ever really tried to hide.(Damn straight) It's not that he couldn't be, it just doesn't interest him. He prefers his reading activities to stop at Busty Asian beauties, or to surfing porn on the internet. (Sounds good to me)

Dean prefers to use his hands, deal with more physical activities. (Hell yeah) He could strip an engine or a gun and consign it all to memory before rebuilding it all back up twice as quickly as when he'd torn it apart. He was combat honed, focused and he delivered. He just chose to hide behind booze, sex and food, because why the hell not? (Yeah, why the hell not?)
Sometimes having people underestimate you was a good thing, and people often did. On occasion it had even been a life preserver. Not that he cared; at least that's what he told himself before going to sleep at night. These people were nothing to him, other than monster food, or people who needed to be saved.

The whole saving people malarkey is what turned him onto his next friend…alcohol! So he liked to drink, big fucking deal.(Yeah, chew on that) It helped him cope. Someone dies, drink! Someone fucks up, drink! Someone actually manages to break down your closed off emotional state, then screws you over, drink, drink, fucking drink!
Drink until you fall unconscious and nothing hurts anymore…or until you wake up with your head down the toilet bowl, your hands sliding in a puddle of your own vomit as it pools by your knees. (I thought we agreed never to talk about that moment again) Yep, drinking was good, in fact booze is one friend that has yet to turn him around and bite him on the ass. He and alcohol still have a very long time to ride together, and it's a pleasant thought. (I really need a drink right now)

Baby! He loved his baby. (Don't forget ma baby) For so long she was the one he spilled all his secrets too, who knew every raw nerve and every tear that he had ever spilled. She was his comfort blanket, his bed for the night; she was his past, his present and his future, because he would never let her go willingly.
For so long she was his best friend, the one he told things to that he could never share with his brother, or the things that no amount of booze or food could ever numb. She never judged him, just listened and brought relief.
Baby was the first to know how he felt about the angel, the one who helped him to sift through all his confusing emotions to get to the truth. Sometimes he had even lashed out at her, but he always rebuilt her. Smoothed her out and caressed her until his hands bled and she gleamed like the day his father had drove her off the car lot. (I screwed my first chick in that car. Good times)

Then there's food. So technically pie could be lumped into this mix, but Dean is talking about real food here, greasy, heavy, artery clogging, fried and battered goodness. Oh yeah, food is good. He likes food, the way it lies heavy in his gut and sates him. Only good friends fill that empty hole inside you. (And bacon cheeseburgers)

There's the constant prevailing force of Bobby too.(Dude, i love you man) At first nothing more than a mere father figure, but now a good and true friend, even if he is somewhat gruff and short tempered. Robert Singer is the one he turns to when Sammy breaks his heart, or falls short. He's all the other family Dean wants or needs. (At least that's what he thinks until a certain halo wearing dude walks into his life. [Hey! I'm supposed to be doing the commentary around here, bitch!])
After John's death, Dean was content with his family unit of Sam and Bobby, and that scraggy cat who hung around the salvage yard who on occasion he fed scraps too. (I call her bones) That was his family, and he believed it to be impenetrable. Hell, he even saw himself like Bobby in the future, half drunk, grizzled and miserable, but with a purpose in life. (Doesn't seem so bad)
Others had come close to acceptance of course. Helen and Jo, they were battering at the hatches of his safe haven, they were close to seeking entry and acceptance into that cosy domestic bliss that made up Dean's universe. But they went off and died before he could truly let them in, sometimes Dean regrets that they were never as close as they could be, even though they were probably close enough. (Screw you for bringing them up)

And then there was Cas! At first he was nothing more than an irritant, the one who gripped him tight and raised him from Perdition…. (Yadda, yadda, yadda! Let it go Cas, that stories getting old. You saved my life, okay you saved it a few times, but come on, seriously, dude, you gotta let that drop now. I know everything you've done for me; I'll never forget what I owe you. Damn, I love you, okay, now just shush. No one wants to hear it anymore) Then slowly Cas became a friend and then a brother…then inevitably something more. (Profound bond be damned, this was meant to be)
Dean always had a hard time defining his relationship with Cas, where it began, how it developed where it was going and where it would end. He had been blindsided, taken as much by surprise by his developing feelings than anybody. Why? Because he wasn't gay, that's why. (I'm so not gay, and anyone who says as much, will get my fist in their face) That was one fundamental truth that Dean knew. Nope, he wasn't hot for cock, never was, and never would be; unless the owner of said cock was one Castiel, Angel of the Lord. (wink, wink. Man, you're killing me here) So it was to be expected that this revelation would pose a problem in the life and times of the elder Winchester. (No kidding) Castiel had got under his skin, buried himself as deep in his soul as the hand print burnt into his flesh.
Cas is now his greatest friend, his lover, his everything: his sun, moon, stars, his whole friggen' universe. (...)

So there you have it. Dean doesn't need any more friends. He has all the friends he needs.
Through all the adversity and challenges life will throw at him, he has everything he needs to make it through.

Dean Winchester considers himself a rich man indeed.
(Amen)