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Toby is Tristram's uncle, Walter Shandy's brother, and a loveable doofus who loves his war toys.
In the early eighteenth century, and for quite a while before that, men—especially the rich ones—were men. They drank, they hunted, they screwed around, they told dirty jokes, they laughed at women, and they basically carried on like a bunch of bros. Toward the middle of the eighteenth century, though, a new model of masculinity started to catch on.
These new men were classic Sensitive Guy, although the word for it then was "sentiment" or "sensibility." They were gentle, kind, respectful, and they sure weren't trying to get into your pants (or up your skirts)—or so they said. There was even a book called The Man of Feeling, written by Henry Mackenzie in 1771, about a guy who has all these qualities and then some. Toby's straight out of an eighties romcom and bending over backwards to be a sweetheart.
Toby never really got past the kindergarten girls-have-cooties phase. Dirty jokes are constantly going over his head because hey—all he's really into are his fortifications. Most of all, he's got a holy terror of girls like the super-aggressive Widow Wadman. When he learns that all she's after is his penis, he swears off women entirely. He ends up so ignorant that he "knew not … so much as the right end of a Woman from the wrong" (9.3.2). (Yeah, we're thinking that would pretty much rule out marriage.)
Looking on the bright side, Toby isn't some player with bad intentions. Mr. Shandy, not to mention Tristram, wouldn't think twice about tumbling some nice peasant girl—or a friendly widow, for that matter. And here's Toby, who can't even work up the nerve to talk to one—let alone feel one up in the back of a car.
Tristram sympathizes with Toby even while he's poking fun of him behind his back. Check out this example: Trim is telling Toby about a woman who's taking care of him after an injury. He describes the woman stroking his leg: "The more she rubb'd, and the longer strokes she took—the more the fire kindled in my veins … my passion rose to the highest pitch—I seiz'd her hand …" and just when you think things are really about to get X-rated, Toby interrupts: "And then thou clapped'st it to thy lips … and madest a speech" (8.12.17).
Um… no, Toby. We're pretty sure that's not what happened.
Toby's an "Aw, shucks!" kind of character who always sees the best in everyone. Look, he has a "benignity" of heart that "interpreted every motion of the body in the kindest sense that motion would admit of" (3.5.2). This is the classic guy who wouldn't hurt a fly buzzing around his nose—literally. When Mr. Shandy throws himself on the bed after Tristram's nose is broken, Toby puts up with his nonsense until he feels better. He has "infinite patience" (3.39.3) that often makes Mr. Shandy regret being a jerk to him. After his pipe sends Mr. Shandy into a coughing fit, Mr. Shandy asks that his "brains be knocked out with a battering ram" if he ever insults Toby again (3.14.9)
Toby just wants to do right by his buddies. Trim's retirement plan is totally taken care of (and a good thing, because who else would help the clumsy oaf?) Even random strangers like Le Fever get the Toby treatment when they fall ill. After Le Fever bites the dust, Toby educates his son, sends him off to school, and gets him set up with the army. When he's wounded in the army, Toby plans to take him in and even hooks him up with a sweet gig tutoring Tristram.
It's no wonder that Tristram's a big fan of Toby. In some ways, Tristram Shandy's pretty Toby-centric. He's not the world's smartest guy, but Tristram's got his back.
Toby definitely has some issues to work through. Tristram tells us:
"My uncle Toby would never offer to answer [Mr. Shandy] by any other kind of argument than that of whistling half a dozen bars of Lillabullero.—You must know it was the usual channel thro' which his passions got vent, when anything shocked or surprised him" (1.21.19).
In other words, Toby whistles like a steam engine when he gets upset. We know that it's a coping mechanism, because Tristram compares it to his father's approach to dealing with Bobby's death: "My father managed his affliction … indeed differently from other men either ancient or modern; for he neither wept it away … or slept it off … or hanged it … or drowned it … nor did he curse it, or damn it, or excommunicate it, or rhyme it, or lillabullero it" (5.3.3). So Toby's a bit of a weirdo in that respect.
Plus, you better believe that Toby has a hobby-horse—he's war-obsessed to the max. Dude's lucky that World of Warcraft hadn't hit the scene yet. Sure, Tristram describes Toby's obsession with fortifications as innocent, but this is a full-bore, grade-A, TLC-reality-show worthy obsession. After all, it's indirectly the cause of Tristram's accident. And Toby even has to make an excuse for being obsessed with war, which is not the most normal hobby for a peace-loving bloke. It's been with him from birth, he says, and he can't help it. It's not that he likes to see people die, but he loves military strategy and history.
In modern terms, we might talk about his obsessive re-enactment as a way of coping with his injury. He's a wimp who's trying to front as a big, masculine dude.
Toby and Tristram are kind of similar (hear us out). They're both big softies deep down, they both get a little frustrated with Mr. Shandy, and they both have some kind of groin wound. If all the characters really are different aspects of Tristram, then talking about Toby may help Tristram cope with his injury. Tristram's hobby horse is the somewhat obsessive recounting of his family history and the various traumas that have formed his identity—broken nose, wrong name, mutilated penis—and Toby, in psychological terms, is someone who Tristram can transfer his own feelings onto. Both of these guy have had rough lives—you've got to sympathize.