I was going through the Archives and I realized something that seems a bit odd, I might be completely off in this, so if I am feel free to correct me and call me an imbecile or other things. But looking through it, it seems that Marten seriously has horrific things happen to him every time he's assertive or plans to be.
(Timeline is based more in terms of how it went in his life as opposed to how the comic presented it, I realize some stuff might be out of order)
1) Make a cross country move for a woman he loves in college, when he gets there he is nearly broke, she pretty much ditches him and breaks his heart.
2) Marten goes to quit his job, or as he puts it the glorified office bitchery, and finds out that he is in fact fired because the department shut down, this is more a denial of closure and "You can't quit, we just fired you, now flail in impotent rage, aww you tried to grow a spine, how cute."
3) Marten sets boundaries with Dora, Dora violates them. Marten calls Dora out on it and ends up getting dumped over it. He is currently miserable and his mother who allegedly came to help him get over it seems to be actively trying to exacerbate the problem rather than help it.
To put it another way, each time Marten tries to be assertive the universe seems to actively punish him. Any comments?