I really enjoyed reading bfleser’s post and agree with much of it, although you are much kinder about Jimmy’s “awkwardness” than I’m going to be.  First, those damn peaches.  I found the recurring symbol of peaches important in showing Jimmy’s repressed sexual nature.  Peaches have long been associated with female genitalia and sexuality and I believe that this may explain why it keeps popping up in the book. The description of the peach by the old man in the airport says it all:  “A soft, single-seeded stone fruit, with a pinkish, red-tinted downy skin and moist, dewy flesh”.  Peaches are either out of Jimmy’s reach or he avoids them.  For instance, we first see the peach dangling high above the scene showing a bloody Amos, killed by his father because of the missing truck, the truck that would transport Jimmy to his first date and possibly toward a sexual encounter.  On the next page, we see Jimmy as the robot, leaning as far from the peach tree as possible (this may be a stretch, as it could simply be Jimmy slumped over in sleep).  Also, in a flashback scene, James eats sugar infested with bugs rather than eating a fresh, ripe, juicy peach.  I find it interesting that most, if not all of his thoughts about women end with them cuddling, rather than having sex.  Even his imagination recoils from the thought!

So, I think Jimmy Corrigan is a sexually repressed boy-man with a highly active and very disturbing imagination.  He has been seriously damaged by his relationship with his overbearing mother, as we can see from his unfortunate attraction to the equally overbearing Peggy, from his office.  In fact, women in positions of authority seem to turn him on (witness his fantasy about the doctor). His uneasiness with women is matched only by his hostility toward them.  Of course, they seem to constantly reject him and not in a kind way (Peggy and the woman on the plane who accuses him of staring at her breasts are two examples), so this is perhaps understandable.  This love/hate is reflected in Jimmy’s (Chris Ware’s?) borderline misogyny and objectification of women, which runs through much of the book.  This is first seen in the comments of his male co-worker:  “I’ve made it my personal rule not to tell any chick I like her until I’ve fucked her at least six times”, a sentiment closely echoed by his father later in the book – “never tell ‘em you like ‘em until you’ve ‘done’ ‘em”.  And it doesn’t help that his dad then says “How’s your mother, by the way?”, a comment sure to add to Jimmy’s sexual confusion by forcing him to see his mother as a sexual object.  Soon after this, Jimmy’s imagination has him in bed with a “cocktease whore” who had the temerity to say ‘no’ to his sexual advances because she doesn’t feel ready.  And, again, when he listens to the tape recording of the couple walking by arm-in-arm (the woman says to the man, “You’re the most wonderful guy I’ve ever met…I think I might be falling in love with you”), his response is to laugh (bitterly, I think) and call the woman a “bitch”. All of this shows his skewed vision of women, which probably stems from his abusive past.

Jimmy is a mess.  While I do have some sympathy for him, he makes me terribly uncomfortable.  His mild manner belies a seething cauldron of fury ready to explode at any moment.  If I were Tammy (the new girl in his office) I would ask to switch desks.