The CW's Dean.
Apart from that, he finds it difficult to make a lot of friends. But there was one character on the show, aside from the brothers, who developed a strange connection with him that went beyond definition. This was the demon Meg. Although they should have been enemies, the two worked together on the same side, and even had a bit of a romantic connection... but were they really true friends?
Meg Was Castiel's Enemy
When Meg and Cas met for the first time, the two were clear enemies. Cas was a morally high angel who considered Meg an abomination. He even deceived and threw Meg into the holy fire in which he had himself been trapped.
Meg, on the other hand, was a Lucifer loyalist who considered the devil her father. There was no element of friendship or even a hint that they liked each other at the time.
Neither Cas Nor Meg Is Capable of Human Feelings
Castiel is an angel who is unable to feel human emotions, although his love for humanity has made him more capable of appreciating human sentiments now. He is clearly very fond of the Winchesters and Jack, but it is doubtful whether his friendship goes beyond that.
Meg too is a demon who is devoid of human feelings and her connection with Cas is not really a friendly one, to begin with.
Cas Is Famously Shy Around Women
Cas is not just reticent in general, he is also particularly shy around women as evidenced time and again.
Meg, seductive as she is, is not exactly friend material either. Although she looks at Cas as if he were candy, she doesn't seem very eager to make friends with him.
The Winchesters Were Using Meg And Vice Versa
Meg first came on to the scene as an antagonist in an opposite camp to that of the brothers, along with the demon Yellow-eyes.
Meg's association with Castiel was first and foremost through the Winchesters when circumstances made her a so-called ally of the brothers. But even the boys didn't really trust her enough to see her as a friend - either to them, or to Cas. If anything, they were using her in the fight against demons and Meg, too, would have benefitted had they successfully taken out Crowley.
Meg & Cas Share A Strange Sexual Connection
Meg and Cas seem to be sexually attracted to each other. The two have a weird physical connection where Meg makes remarks full of seductive innuendos and Cas, in his own shy way, responds to her advances.
Meg is also the one person Cas is known to have kissed ionately, a kiss they both seemed to enjoy quite a bit. Meg has her own nickname for Castiel --Clarence-- and the latter doesn't seem to mind it. Cas even goes as far as to compliment and appreciate Meg for her beauty when Meg takes on the role of his caretaker.
Cas Compliments Meg Only When He Is Incapable of Rationalization
Cas kisses Meg when he is still very much sane but in season 7, he becomes favorably disposed to her only when his guard is down and he seems disoriented for a while.
Cas shows goodwill to Meg at a time when he is not in his right mind and although he re that he is an angel, he is not himself. So any feelings he shows towards Meg at this time might not have been those he would have shown in a more rational state of mind, and should probably be taken with a pinch of salt.
Meg Wanted To Take Advantage Of Castiel's Mojo
Although the two clearly share an unusual connection, Meg is not above using Castiel's angelic mojo for her own good.
Meg, oddly enough, takes on the task of tending to Castiel when he seems to lose his bearings. But she is shown to have her ulterior motive, which is to somehow use his powers to keep herself out of harm's way.
An Angel And A Demon-- Can They Really Be Friends?
There is a fundamental difference of principle between Cas and Meg given that one is an angel and the other a demon.
Of course, the show has repeatedly shown the most unlikely people team up with each other to get things done. But between Cas and Meg, there are miles to cover before they can even qualify as friends since they are polar opposites in of world-view if there is any such thing for an angel and a demon.
Both Are On Virgin Ground Here
Meg is quite clearly the first demon Cas had let himself be even remotely drawn to. Demons, on Supernatural, although a necessary evil, are not really people one can put their faith in.
Cas too, one can assume, is the first angel that Meg has grown to be fond of. This is virgin territory for both since neither has probably felt like this before for any other angel or demon. Given this context, it's hard to imagine them becoming buddies.
Theirs Is Only A ing Acquaintance
At the end of the day, Meg and Castiel's relationship is a ing one. Although the two shared some brief chemistry in the short time they knew each other, they never really bonded as such-- in a friendly way or otherwise.
Meg was one of the many characters that Cas has come across fleetingly ever since he ed the fight against the apocalyptic forces with the Winchesters. They did flirt now and then, as much one can expect of an angel and a demon, but there is very little trust between them and hardly any sign of true friendship.