I’d go on and on about how utterly awesome your posts are but right now I’d like to seek your much-coveted wisdom on the workings of the male human mind.
So there’s this guy I like (surprise, surprise!) who for anonymity’s sake I’ll call Jake Gyllenhaal or JG for short. JG is my friend’s older brother whom I’ve developed a crush on some months ago. Here’s my dilemma: I’m not sure if he likes me too or if he’s being nice to me because I’m his little sister’s friend. A part of me also believes that perhaps he has “sister-zoned” me or that he thinks he can only be an older-brotherly type of friend to me, given that I’m his sister’s age. Lately however, he’s been doing certain things that are kind of messing with my head. Like one time my friends saw him staring at me and just yesterday I caught him staring at me so many times that I’m pretty sure it wasn’t mere coincidence he was looking my way. I seriously do not know what that was all about. Sometimes, he would send me stuff about this TV show he and I are fans of (e.g. pictures, sneak previews, etc.) and one time he even promised to give me a copy of this series starring an actor he knows I admire (something I honestly don’t remember asking him for). Another time, during an online group chat with a volunteer group we’re both a part of, he goes, “Look [my name]! I found this funny picture of [actor from TV show we like]!”
But even though JG and I would occasionally talk and joke around a bit (He almost always initiates the conversation, by the way), most of the time he’d act like he doesn’t even see me (Then again, I’d also act like I don’t see him because I’m an awkward goblin around people I like). We’ve never flirted with each other and there’s been zero physical contact between him and me (even shoulder/ arm touching). Does he like me the way I like him? Or does he like me as a pseudo-little sister because of my relationship with his real little sister? Or is he just an extremely nice guy whose niceness means absolutely nothing romance-wise? But then what’s with all the staring? Please help me, Jono!
You guys know by now that I tend to think almost anything indicates that a guy likes you. I'll tell you that if a guy smiles at you, it's because he likes you. If he sits next to you in class, he likes you. If you are in a room, and a boy is also there, he likes you. If you are in a room and a boy is not there, it's because he's nervous, because he likes you. In this case, I'll grant that a lot of what JG has done could be construed as simple friendliness (nerding out over TV shows, joking around with you), but then we get to the part where you catch him repeatedly staring at you.
Now, I may not be a big-city lawyer [hooks thumbs under suspenders], but where I come from—being male—this is a pretty reliable sign of interest. Once or twice is coincidence, but you don't keep gawking at someone you think of as a little sister. In fact, if I accidentally do that across-the-room-eye-contact thing with someone I'm not interested in, I actually go out of my way not to do it again, so as not to give her the wrong impression. On the other hand, I am a huge dork who overthinks these things, so I'm not saying that other guys necessarily consider eye contact this meaningful. But on the third, vestigial hand, there's the fact that he always initiates your conversations. You generally don't keep contacting someone you're not interested in unless you are trying to sell her extended cable service.
None of this is 100% definitive, because high school boys are a riddle wrapped in an enigma that has forgotten to take a shower. Maybe he's just a friendly guy; maybe he has a habit of staring at random girls because he is a crazy person. The only thing that makes me unsure about his intentions is that you said he'd act like he doesn't even see you; a guy who likes you isn't going to literally walk past you like you're invisible, though he won't necessarily drop everything to fawn all over you either (in fact, when a guy is all "Wow, you are sooo amazing, and I am as stupid as a butt," this is usually a bad sign).
But the thing that matters most here is consistency. If he used to ignore you, and now he's constantly going "DUHH?" and gawking slack-jawed at you from across the room, it's possible that his interests have simply changed. I'm sure you've experienced this yourself. You meet someone, and your only impression is "Well, that sure is a human being." You remember him as a vaguely male-shaped body with a question mark for a head. But then you hang out with him more, and get to know him better, and before you know it, you're having dreams about marrying him on a tropical island, and then you look down and you are in your underpants and you forgot to study for a big test. My point is that romantic interest sometimes just develops out of nowhere, and if his current behavior consistently implies interest, then his past behavior doesn't matter too much.
As for what to do about this, there's a good chance Jake Gyllenhaal doesn't know what to do about you due to Maggie Gyllenhaal. Surely you realize it would feel weird for him to be attracted to his little sister's friend. I always advise being more overt about your interest in a guy, but that's even more relevant here, because I think he honestly doesn't know if it's morally okay to like you. I'm not saying you have to be like "YO JAKE, HOW ABOUT THIS ACTION," and stick your tongue in his face, but you do need to give him some indication that you wouldn't feel creeped out by his interest. One way of doing this is to stick your tongue in his face, of course, but you could also do it by being the one to contact him more often, occasionally saying flirty things and generally seeming interested in him (as opposed to just your mutual hobbies). And you should be sure Maggie G is okay with this too; you don't want to risk a friendship over potential boy romance, because we're not very good at it anyway. Make sure she's on board, and if she is, start giving this guy some signs that he's allowed to like you without someone alerting the cops.