So I read some of your advice, and it's actually good! (Most of my guy friends aren't very good at it.) So I thought I would ask this question that's been bothering me for SO long: So i'm a sophomore in HS and i like this junior who rides my bus. He's friends with most of the guys I know and I think he's really cute and would like to know him better. Problem is that if I talk to him out of the blue, he'd know I like him because no teenager will come up to you randomly and greet you unless they like you, and I want to make it subtle. When we're waiting for the bus after school, most of the time he's surrounded by friends, but somehow he always looks at me and i look back and we hold for a few seconds and then look away... and inside the bus when I come in, he always looks at me until I sit. When he comes in and notices me, he sits in the row in front of or behind me, but always on the opposite side of me. I want to sit with him, because inside the bus he's sitting alone (most of the time), but I wouldn't know what to say to him. Also I don't want him to think I'm too pushy or annoying. I was thinking that maybe I could ask if I can sit with him and then compliment his shirt or something, but idk. Anyway, thanks for your help! Xoxoxo -& sorry this is so long :b
Oh my, this is an easy one. Here are some things you could do that would indicate to this boy that you like him: You could hit him in the head with a golf club. You could stare directly in his eyes and hand him a dead bird. You could punch him and punch him until he was no longer alive, and his last thought would be "Wait a minute, I think this girl likes me! Glurk I am dead."
You said it yourself: if you're approaching him, he'll already have jumped to the conclusion that you like him regardless of what you say next. Well, okay, not completely regardless; if you had forced me to approach some random girl while I was a sophomore, I would probably just have barfed up a bunch of tacos, even if I had not eaten any tacos, and then run away in terror. But you're not me, and so I'm pretty sure you're overthinking this. Here are some guidelines to making an approach like this anyway (though I don't think you need them).
1.) The subtle approach
I agree with what you said—he'll know you like him, because no teenager would just approach out of the blue—but, I mean... you do like him. This is that game that both genders like to play—you don't want to seem too eager, so you act aloof and uninterested, then he pursues you, and you win the grand prize, which is the exact same relationship you would have if you'd just said, "Hello, I like you." Of course, if you keep playing this game, you're likely to keep winning the consolation prize, which is absolutely nothing. Guys are much more willing to say yes to girls than vice versa, even girls they're only moderately attracted to; sooner or later he's going to walk past a traffic cone with a wig on it, and he'll think "Welp, that's good enough for me," and then all your intricate machinations will be for nothing. But I digress.
If you absolutely must make this approach without tipping your hand, I guess you could just manufacture a scenario where you seem to have to sit by him. You could look around with one hand shielding your brow, like an explorer, then sigh heavily as you realize there are no open seats. Then you could look all disgusted at the prospect of sitting next to this terrible oaf, plop yourself down on the seat next to him, and sit there in total silence. "I HOPE THIS GUY DOESN'T GIVE ME IDIOT CANCER," you could pointedly text someone. Or you could just sit down and smile, which is much less wacky but far more likely to work (in which case skip to #3).
2.) Say something normal
I wouldn't fixate too much on the exact thing you should say. Imagine if you say "I like your shirt," and he's all "Oh, I hate this shirt," and you reflexively say "Me too!" and then look away and stuff your entire fist in your mouth. There's no perfect cover that's going to conceal why you're approaching him anyway, so concentrate more on how you say it. Keep your cool, don't come on too strong, and just treat this like a normal conversation, the goal of which is to exchange ordinary words between his face and your face. Choose something to be genuinely curious about ("does that guy like or hate his classes?"), and that will keep you from getting flustered, which will keep you from blurting out something like "I like your Sarah, my name... I'm... shirt."
3.) Be prepared for him to say something idiotic.
There's about a 50% chance that he'll reply to your "Hello!" with "Blargh!" or something equally smooth. Look, you're better at this than guys generally are. If you just come and sit down next to him, he's as likely to say "Hey, what's your name?" as he is to say "PTHTBHTT," followed by "Oh no, now you are covered in Mountain Dew, oh gosh." But all of this is a good sign, because he's even more likely to act like a moron if he likes you back. If anything, the challenge for both of you isn't what, specifically, to say; it's saying it like this is a totally normal and not-at-all-terrifying conversation.