Thanks for the compliments, although, for me they're pretty much standard debate sized posts.
But in any case, I would like to address Lurking's idea of Torg's attitude as a defensive mechanisim. Because
it is a defensive mechanisim. In two folds really; the first is that because Torg switches to goofball mode, he won't have to worry about showing weakness to those around him, and second (perhaps more importantly), he doesn't have to acknowledge it. When Torg is under pressure, he doesn't think on it, he just gives a goofy reaction, often with puns and horrible jokes. In fact, if you look in his first visit to the Dimension of Pain:
Horribus: Why can’t we use his fears against him?
Psyke: The long of it is, he does not explore the consequences in depth, so he has no unknown fears to confront. And his memories are limited, so he has no fears from his past. The only things he seems to “fear” stem from simpler things we would not even regard.
http://www.sluggy.com/daily.php?date=980505
This is how Torg deals with stress and fear; he just doesn't explore it, he ignores it and hides under the goofball act in order to deal with the situation. The Zoe incident is different, simply because it was strong enough to shatter Torg's paticuarly effective manner of dealing with things. That's why he became so depressed for so long, and why he still has issues with it now.
And as for the idea of Torg having a poor relationship with one or both parents...that's actually a very distinct possibility. During the Stormbreaker Saga (if I recall correctly), he mentioned fencing, and although it was a joke, the figure scolding him in the memory sounds like a very harsh father figure, so that may be it. Granted, his personality sure does seem like there's an issue between him and his parent(s), since something like that typically develops due to extended periods of emotional damage, although it doesn't per say have to be a parenting issue. He could have seen a particuarly horriblie murder, or some such.
Of course, the fact that we've seen both Riff's and Zoe's parents, but I fail to even recall one event including Torg's parents, is pretty telling in how close they are. I mean, Dr. Lorna is Riff's mother and they've spent more on-comic time hanging out together than Torg's. Granted, this is the same for Gwynn, but given her mood swings, they're were probably happy to get rid of her.
In any case, onto Riff!
It was mentioned during his sessions with the therapist, that when confronted with his problems, he put down his excessive inventing to when Dr.Lorna actually seemed proud of him that ONE time at a science fair, and he's just been inventing ever since just to get that same reaction (although it may not be a conscious act most of the time). Given the fact that he'd managed to impress his mother, and that he actually entered a science fair, I suggest that Riff already had strong tendencies toward this area, and became obsessed with being smart, inventive, and successful simply because it would make his mother proud.
Now, to understand this, we should also look into his parents for a moment. His mother is a bitch, but why is she so? Clearly no one is born that way. Well, I suspect that Dr. Lorna was actually a lot like Zoe when she was younger. She was a young woman looking to make her way in the world, and then she met Riff's father. Now, according to Zoe's comment of "she must have had him young", the manner in which it seems to be potrayed is that she was still in highschool when she had him, which would explain why she and his father didn't last long. Well, at best we could put that around the ages of 8-10, which would put Lorna at 25-27 when the fair took place, which would have had a very massive impact upon someone who feels like they've been neglected for most of their life. In any case, I think Lorna started heading south when she became pregnant with Riff, simply because of the stress given to someone at that age, and in the seventies to boot. Lorna probably lost most of her friends, and was/is probably a perfectionist. This would explain her own attitude, as to why she constantly blames others for her troubles, is over critical, always on the offensive, and is always playing the victim (or at least, she seems like the type to do that). Now take that person, and put them into a position where her public face has been tarnished, and now she's stuck with a kid. She'd hate the father, and probably to an extent, blame the child, although this may not be a conscious act in and of itself.
His father however, is another story. The way they keep in touch suggests to me that although Riff knows his father loves him, his father was just never there. In essence, he's been given gifts, praise, and attention from his father, but such things are from afar, and he was never around when Riff really needed him there. This also suggests to me that although Riff's father might be a great guy, he's probably more in love with his work than he would be with a woman, and that probably didn't help Lorna out at all, and I'm sure what help sent her down the path of crazy.
In any case, when we take these two individuals, and we pass not only their natures, but their nurture along to Riff, we see a very sensative personality formed from jagged glass. Riff is constantly throwing himself into his work, ignoring all others save for his buddy Torg, who is perhaps the only family he's ever truly had. This would impart, explain why someone as hot headed as Gwynn, could never really understand Riff, or possibly hold a successful relationship with him. Indeed, she seemed more pissed off that someone dumped her, rather than out of a true feeling of no longer having a relationship with said person. Why Riff would be attracted to someone like that in the first place is to an extent, understandable; since I do recall someone mentioning (on some other forum), that people typically look for aspects that not only match them, but to an extent, their parents. This would explain why Riff might be attracted to someone as reckless and spiteful as Gwynn, as in a way, she acts a great deal like how I'd imagine a young Lorna would have acted.
Now granted, there is another aspect to Riff's personality that isn't as apparent with his other issues, and that's his burning desire to push the world into black and white. To me, this could be a few things, but I doubt it's something that's just there to distract him from his deeper issues, since Riff seemed really hurt when he discovered that he'd been working for the bad guys for years. I think this might be a part of him that came to being because he was so emotionally damaged as a child, with him identifying those that cause pain to be evil. As in honest-to-God-satan-evil you see in the bible. In his mind, there is white, and then there is black. That's why he had such a hard time seeing Sam as nothing more than an undead minion of evil, and why he acts like the group's paladin. Now granted, he isn't above summoning a demon for beer and risking the world, but that may have just been part of a secret desire for the demon to have gotten loose, and Riff having to go out in a blaze of glory. In fact, we see this a couple of times in the series. During the Kzk story arc, we were told that an exchange of energy was seen flashing at the scene of the battle. Now, given that the banishing would have failed, then Riff would have assuredly switched to guns blazing, and I wouldn't put high stock in riff surviving in any way. Another push to be the hero was clearly in the arc where the house got pulled into another dimension; Riff went out of his way to stop Gwynn from doing something, claiming he was "union", suggesting that he had to do it because he's the hero, and that's what a hero does. Now granted, he had a better idea, and it worked, but I think it clearly shows that Riff has a great desire to be a hero, but it isn't so much because he cares about others that much, but more of for himself (although, again, this may not be a conscious act).
However, this isn't to say that Riff is a walking cloud of despair, because we clearly see that he's more than willing to be goofy, even to the point of endangering himself and others. For the most part, we see this is when Torg is around, and everything is going well; but when Torg is gone, Riff loses his anchor and slowly begins to fall apart. I think the reason for this is because Torg was Riff's distraction. With Torg around, Riff didn't really have to deal with the problems he'd grown up with. The loss of Torg really shattered Torg to an extent, but I don't think it was the actual loss of Torg, or the fact that Torg matured since that time that's really done a numbering on Riff. Rather, I think it may be the fact that he's having to acknowledge the fact that he HAS problems. Before, Riff would just shrug and say "I dunno", or "let me check my notes" and never get back to it.
I believe that when Riff and Torg were younger, Riff would hang out with Torg because he needed the distraction (that is not to say he didn't like Torg, or doesn't care about him, but rather it was the need for a distraction that drove the friendship at first, and that Riff was relying more on Torg than he had at first realized), and as the friendship grew into something more stable, and as they years passed, this aspect of the friendship was forgotten, and to an extent, had healed somewhat. But when Torg was lost, Riff was not only faced with the tragedy of having lost his friend to a demon infested area (very dangerous), but he was forced to once again acknowledge his other, deeper issues. This is why despite Torg's return, he still doesn't seem 100% because of the emotional issues he's facing at the moment. And in a way, this shows. Zoe's comment on him becoming Torg is exactly that; Riff is in a way, starting to pick up Torg's habits of dealing with stress and deeper emotional issues.
As for his failings in his love life...well, there is the fact that Riff has never really been shown what a loving family does, and I suspect that he just does what his father did to him; he offers love and support, but he's NEVER really there for her when she needs him, and he's diving into a project rather than building their relationship.
Anyhow, my two cents.