I'm [...] supposed to be just starting my own family, but there's been a setback [...] and you wouldn't think you could get any more depressed while sitting shiva for your father, but you'd be wrong. Suddenly, I can't stop seeing the footprints of time on everyone in the room. (8.10)
What's got Judd even more depressed than his father's death? Comparing himself to the old married couples at the shiva. He's looking back at his own "footprints of time" and wondering where he's going to be leaving footprints in the future. From his perspective, it's a lot easier to walk into the future if you've got a partner at your side.
And now I have no wife, no child, no job, no home, or anything else that would point to a life being lived with any success. (8.12)
Judd comes from a pretty successful, mainstream family, which gives him specific expectations about the path that his life will take. Imagine that shock when he wakes up to find that he doesn't have anything resembling the life his parents had—something that a lot of us are going to feeling, unfortunately.
To have nothing when you're twenty is cool, it's expected, but to have nothing when you're halfway to seventy, softening and widening on a daily basis, is something altogether different. (8.12)
Notice how Judd compares himself to a twenty-year-old? Yeah, that's not something you want to be doing in your thirties. Your thirties are a time for looking down on people in their twenties, not living their lifestyle. Get it together, man!
Linda's smile is sad, ragged, and somehow beautiful, the aching smile of the long-suffering. "You learn not to think about what might have been, and to appreciate what you have." (8.33)
Judd is not the only one who feels dissatisfaction about his life. Imagine that! It's almost like he's not the only one whose life didn't turn out the way he expected. (But don't try telling him that. He's still wallowing in his own ego.)
I shake my head. "It's just hard to see people from your past when your present is so cataclysmically f***ed. Horry nods sagely. "Welcome to my world." (8.92-93)
Horry knows a thing or two about dissatisfaction. One minute, he was a good-looking kid with a pretty girlfriend and his whole life ahead of him. The next, he was homebound and living with epilepsy, not even able to move out of his parents' house. So maybe Judd should stop feeling so sorry for himself, hm?
The point is, I have this fake leg clamped to my thigh [...] And when I remember that I'm an amputee, I experience this moment of abject horror when I realize that when I get home I will have to take off the leg to go to sleep and I can't remember ever having done that before. (10.1)
Judd's dream about an amputated leg is a way for him to process being separated from Jen. He can't remember how he lost it and, with one leg, he feels like there's nowhere for him to go. Gee, it's nice when your subconscious uses such straightforward symbols.
Under their scrutiny, my rage dissolved almost instantly, replaced with the hot shame of public emasculation. My wife had slept with another man, so what did that make me? (14.31)
Judd's dissatisfaction has a little to do with his own feelings and a lot to do with his desire to avoid public shaming. It's bad enough to experience a broken marriage—it's so much worse when that broken marriage is out on display.
"I don't have one. No great traumatic event to blame my small life on [...] I tried to make something of myself and I failed. That happens every day too." (16.31)
Once again, Penny proves that she's more than just a Manic Pixie Dream Girl. She's a person with hopes and dreams and disappointments of her own, who's telling Judd that he needs to grow up and take ownership of his life.
At this moment, I feel numb, and if you were to peel away the numbness you'd find a thick mucous membrane of trepidation, and if you were to slice through the membrane, you would find a throbbing cluster of outrage and regret. (20.31)
This is a lot of words to express something simple: Judd's scared that he'll be alone forever. This fear is at the core of everything he does, and—surprise!—it's basically at the core of everything everyone does.
I am not ready to be a father. I have nothing to offer: no wisdom, no expertise, no home, no job, no wife. If wanted to adopt a child, I wouldn't even qualify. (31.77)
Here, we see how Judd's dissatisfaction is tied to his manhood. He has a kid on the way but he doesn't believe that he has the tools he needs to be a good father. (Well, he has the tool to be a father, if you know what we mean …)