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Since I’m re-reading early CO (or I was in Oct 2022): surprisingly enough I don’t think I have posted about this before, but you can’t convince me Simon starting to date Agatha the very same year he started following Baz around is a coincidence. Simon couldn’t understand his feelings for Baz (he wonders if Baz had him on his thrall) (he wanted to be with Baz all the time) and on some level, this scared him. On some level his feelings for Baz were scary. Because Simon was able to exist back then by not thinking and (not to be cliché but) not listening to his heart, trying to fit in perfectly into his role. (Simon indeed “never thought he was straight,” but he never thought he wasn’t either—he never thought about it at all, but heroes with his role traditionally are.)
Simon went for someone who perfectly embodies traditional beauty standards and represents the traditional path forward for boys like him (reinforced by the media and the expectations he would be exposed to). Someone who awakened nothing on him (other than highlighting his terrible self-esteem issues) and thus allowed him to exist purely on vibes and not process shit (which is comfortable, in a way. Romantic love and sexual desire are famously not mild feelings, hence Simon regularly losing his shit around Baz and not being able to handle them). Someone with issues of her own, whose constant kidnapping/exposure to danger programmed her to get used to discomfort and unhappiness too (and Simon wouldn’t register it at the moment, because it’s all he’s ever known. Hell, actual happiness and comfort register as wrong for him).
Simon’s list is pretty interesting to think about in this light. He tells us, when he ranks Penny no.2 (after his favorite food) that he should probably rank his girlfriend higher, because girlfriend. It implies he feels obliged to care more about her—to like her more—but he doesn’t. Agatha is literally last on his list ("he never put her first," he says later, but it’s even worse: he puts her dead last). He has all sorts of excuses to justify this without discovering his actual feelings, but even in his excuses he reveals a lot:
“Too good to be true” if something feels like that it instantly raises alarm bells. But it’s not that Agatha is “too good” for him because he likes her so much (something he does with Baz later because self-esteem: in shambles). It’s more that the idea that Simon can have the stability, security and belonging he craves, which he thinks about in terms of traditional HEA is “too good to be true.” He’s still thinking about it in terms of straight traditions, and it doesn’t fit either of them. He’s even contradicting himself with the “saving the best for last” excuse when he puts Penny second—after food of course—and says “my gf should probably be higher than her.” Like, which one is it—can't be both! "Ranking my favorite things in the world (food and Penny) as no.1 and no.2" and "saving the best for last" (no.10 iirc) is a contradiction. (He says as much when he thinks Agatha "should be higher." His excuse is bullshit!)
Simon doesn’t think about Agatha when she isn’t around (he barely thinks about her when she is around). He doesn’t want to. It’s already indicative that he feels wrong and doesn’t like dating her, but doesn’t feel like he can change that. “He’s not even sure he misses her” —he doesn’t miss her at all! (In WS, when he's more aware of his feelings and himself, he admits to “missing Baz so much” over the summers, and he ties it to thinking about him all the time.)
Baz is not on his list, but he keeps messing up with it. Simon starts talking about Baz way before he even brings it up (way before he starts introducing his favorite food and people and places). Like this, he's doing more than putting Baz first. He keeps interrupting his list to talk to us about Baz: how perfect and good-looking and ruthless he is, how organized he is, how he plays football for the school, how he uses the bathroom (is an early example of how obsessed he is with the guy). He shares so many small details about Baz, and even manages to include something specifically connected to Baz on his list (the pitch, where he spends countless hours watching Baz play) because talking about him before and after the list is clearly not enough. No one occupies his thoughts like Baz does.
Baz messes with his structure, he messes with his thoughts. It hints at something Simon outright says in the following books: his feelings for Baz can’t be contained. They’re too big, too overwhelming. He can’t stop thinking about him. And Simon can’t deal with it—not until he’s faced with the real possibility of Baz not being in his life anymore. That’s when he pushes all his fears aside and snaps into action (something we see happening again with the break-up/getting back together in like… less than 24 hours)