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S5E1: Venus Part 1
Aired: 2005

On the first day of school, Toby is seen only briefly walking with JT and Liberty. He wears a green tee under a green open button down.
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S4E20: West End Girls
Aired: 2005
We wrap up West End Girls with Toby, wearing a maroon tee and his usual glasses. But his hair is kinda spiky, and that’s cool. We briefly see him at the dance being kinda rapey… I don’t know why the writers did that. I mean, you gonna make Toby a creep or not? Pick one.
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S4E9: Back in Black
Aired: 2004
Toby… He wears his polo buttoned TIGHT all the way up. He’s still reppin the 90s/early 00s wit this spiky hair, the horizontal chest stripe, and those teeny tiny glasses. For the funeral or viewing or whatever this thing is, he wears a grey checkered shirt. Man, do we even ever see Tobs cry?
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S4E8: Time Stands Still, Part 2
Aired: 2004
Poor Toby. I hate that we the audience never really get to explore inside Toby’s mind, ya know? Like we are hardly ever in his room. We never get to unpack his trauma. We never get to know his deepest feelings. He’s treated like a prop, even now, being so close to one of the most important storylines of the show. Justice for Tobs! He’s got his spiky hair, his rectangle glasses, and his sling from being beat up for being friends with Rick. Ugh! Also, why tf did Toby never like, get revenge on Spinner and Jay? At the very least like, I wish karma could have struck. Well, did it? I mean Spinner went through some terrible shit. But Toby still has more terribleness awaiting him so keeping karma score will be a task. Anyway, he wears red and an overshirt and, just.. poor Toby.
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S4E6: Islands in the Stream
Aired: 2004
Toby is definitely giving off vibes of wisdom in this episode. Toby is confident in who he is, yet he knows his place. It’s a stark contrast to starry-eyed Rick who thinks anything is freaking possible for some unknown reason. Toby’s self-awareness is actually probably part of what gets him way more kisses in the kissing contest. Toby dresses comfortably – kind of nerdy but also kind of normal. It’s a very balanced style. Polos, baggy jeans, glasses, etc. But the spiked hair makes him seem just a little less nerdy. As if to suggest “I’m a nerd by choice but I don’t have to be”.
Side note, this little kiss-collecting competition reminds me of one my friend and I had in grade 7. We started taking a poll – I think we either asked everyone “which one of us is prettier” or “which one of us do you like better”. Sadly my friend was widely disliked so I won by a landslide, and she was shocked and surprised by it. I am historically friends with extra annoying or very disliked people. I don’t know what that’s about, but it’s worked out fine.
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S4E4: Mercy Street
Aired: 2004
We conclude Mercy Street with poor, forgotten, cast-aside Toby. Nah actually he does play a small part here, helping JT with his penis. Also, in Season 4, Toby has debuted a new hairstyle – we didn’t get to see it well in the last post so here’s a better look – SPIKED HAIR! Good lord can we bring this back!? Actually, both of Toby’s hairstyles have been great imo. Toby hair appreciation moment!
First, Toby is of course swimming in a t-shirt. No shame of course but come on… does anyone actually WANT to wear a t-shirt over their bathing suit? He also has these sunglasses that look like the slick Oakleys we all coveted at the time. I myself had some Foakleys I bought off a dude on the street in Washington DC. Whatever it takes, right? Next, Toby is wearing skate shoes to gym, which is… a choice. Next he is JT’s penis assistant in this red tee, baggy pants, and the skate shoes. I just used to CRAVE those flat soles and thick tongues, man. I loved skate shoes. I unfortunately wore them an undeserving amount considering how little I skateboarded.
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S4E1: Ghost in the Machine
Aired: 2004
Toby is here walking with Emma and Lib, wearing baggy pants and a polo with a horizontal chest stripe.
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S3E19: It’s Raining Men
Aired: 2004
Toby is just being JT’s sidekick as always, wearing maroon shirt with shoulder stripes, and just, well, being there.