It is very easy to adhere to the oversimplification of the character, and the movie forces us to take that path. I mean, Jacob is introduced as this gorgeous, sexy, insanely confident character who barely needs to snap his fingers to attract half the women at the bar, and they are all too happy to experience a night with someone whose reputation is that of a legendary lover. Cliché, right ?
His entire presence for the first half of the movie is one leaning towards a womanizer, he even says things that would approach the misogynistic tone (“The war between the sexes is over, and we won, okay ? We won the second women started doing pole dancing for exercise”) but are immediately followed by a counter argument relieving that impression (“But even though we won, they still deserve our respect”) and that’s Jacob entire undertone during the first part of the movie. He is overly sexual but never toes the consent line, these women are thrilled to sleep with him, and he never disrespects anyone, from the waitress to the store clerks. He’s exuding confidence that can be interpreted as arrogance but he never is. And he hides all of his precious cracks and flaws behind that overconfident appearance that just shatters the minute you actually stop seeing Hot Guy From The Bar™️ and start looking at Jacob Palmer.
The cereal scene immediately introduces a very tender version of him, and from that point on, Jacob’s inner layers starts to show. He is a lonely boy in a vast apartment.
When Hannah asks him to take off his shirt, Ryan’s magic works wonders. He isn’t so confident anymore, and being objectified hurts him. That’s when the wall of charm and attractiveness starts crumbling down and his lack of self confidence shows up. What he shows to the world conceals entire parts of him that are so fragile and delicate he can’t afford to expose them. This is a little boy who lost his father, and grew up with a mother that most definitely projected a vain image over her child. For him to describe her as cold, he probably suffered a lot.
You figure out very quickly that love paralyses him because he saw his gentle dad being mistreated by his icy mom, and that he can’t, for any reason, follow the same path. So when Hannah, quirky, smart, funny Hannah comes around, he is immediately in a position of vulnerability. The cocktail thing doesn’t work. Dirty dancing becomes a shtick borderline ridiculous. And when he resorts to the one thing that he knows he can do to quiet the noise in his mind-sex-she even detects his obsessive compulsive tendencies and she disarms how shameful he feels about it : they laugh about the countless stuff he bought online, that he never uses, and for the first time, he can even put words into how unhappy he is.
And because he feels safe and comfortable with her, he can unmask. He talks about the things that hurt so much. And Hannah takes them seriously and doesn’t dismiss his pain, to the point of him feeling so serene he can fall asleep without having fed his ego (or lack thereof) with a satisfied partner. He probably slept peacefully for the first time in a long time, feeling seen for something else than his body.
From that point on, the mask is off and never comes back. Falling in love is scary but he already cares so much about Hannah it’s not really his choice anymore. She reveals a sillier, lighter version of himself that you can also see by the clothes he now wears : sharp suits are out, relaxed polos are in. He’s in love, and she is everything and he’s so scared to meet her mom because what if she projects over him what his mom did ?
I don’t think we can quite overstate how utterly devastating it is for him to be treated the way Cal treats him when he figures out he’s Hannah’s boyfriend. Jacob’s loyalty is unwavering, he takes hits for Cal, but he doesn’t care. Cal hurt him immensely. The bar scene really underlines how genuinely painful it is that he won’t give him half a second chance, and yet, Jacob still compliments him with tears in his goddamn eyes. And he wants Hannah to call him. This is knight in shining armor levels of selflessness.
The ending shows that he cares about everyone. He values Robby’s graduation so much the sharp suit is back-he’s overdressed ! But he loves these kids. And he wants to show it. It matters to him. And he takes Cal’s abuse stoically. Because it matters to Hannah. And to Cal. His own feelings have no value as long as they are happy. He can take it. It’s probably not the first time he does.
Jacob is probably the most gentle, and one of the sweetest of all of Ryan’s characters but you need to spend a minute with him to actually understand. And because he is so openly sexual, people dismisses him and mischaracterise him so severely.
He can be the softest sweetheart ever AND be openly sexual. These two things aren’t mutually exclusive.