An example of a good organic compliment would be, "Yeah, I really could not get that Political Science assignment last night. If you act this way around other people, when you let him see a few of your vulnerabilities when the two of you are alone, he won't be able to resist. If the thing he enjoys is generally considered weird, unusual, or girls don't normally care about it, you will get some serious bonus points. This is not to say that women should wait for men to talk before feeling like they can talk. Skinny jeans are a safe bet right now, especially if you've got great legs (although skinny jeans make pretty much everyone look like they've got great legs).
If you have a dress code at your school, like wearing polo shirts or wearing certain pants, don't compliment him on it. If you don't know him well enough to know what to compliment, you can always fall back on this.
Confidence, tempered with a few moments of vulnerable self-consciousness, is the sexiest thing for some guys. Be someone that other people want to be around because then he'll want to be around you too. He doesn't want to hear you smack talking other girls or talking about how ugly some guy is.
You want to wear clothes that show him what you've got, while still leaving something to the imagination. You can pair that with a satiny sleeveless top, for example, for a look that tells him you're everything he wants.

Don't make it outright flirty, though, if you haven't established that kind of relationship. Don't be confident like you can't do anything wrong and everything you say is pure gold, that's just annoying.
He wants to feel like he's free to be himself, pursue the things he wants to do, and have some good alone time. Just make it seem like you have other things to do and that not all of your time can be devoted to him. If you have darker skin wear bright, saturated colors in light tones (a white dress on black skin looks amazing, for example).
Wear clothes that accentuate your best features and cling or hang loose in all the right places. Wear clothes that look worthy of a date, not something that you'd wear on a sick-day at home. Your guy wants you to be naturally beautiful, so don't make it look like you have to put on half a MAC store every day. Make sure your teeth are brushed, you've got on some neutral deodorant, and then put on some nice perfume. We all want to feel like we're useful to other people, and if he feels like he's your hero, he'll want to be there for you all the time.
However, if he sees you helping other people, giving honest compliments, and otherwise being a good person, he'll know you're someone he wants to be around.
Find things that you can share in common or try to find enjoyment in his favorite thing to do.

Guys are especially prone to needing alone time and you need to respect him by respecting that need. Wear clothes that would make your grandmother raise her eyebrow but still let you out of the house. Use a little eyeliner, mascara only if you really need it, and just enough eye shadow to give your eyes some shape if they're lacking it. This will show him that you are totally interested in him and leave him longing for a little more physical contact.
Be a little dorky, openly enjoy the things you enjoy, and let your wonderful personality shine through. If he's a decent guy, he'll eventually do the same with you, at which point you can talk about your stuff.
If he feels like conversations with you can't be sustained, he's not going to want to spend time around you. Just make sure that your hair looks like you put in a little effort and not like you plan on spending the whole day at the library or lazing in bed.
Just make sure that, whatever you say, you actually mean it because people can almost always tell the difference. Find the happy coincidences in life, the upsides of tough situations, and the funny moments when you feel like you're about to cry.

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