Be sure it's legal and safe. If you're under the age of consent, do not date someone over the age, even if you believe you are mature. It will become difficult to manage and put boundaries down. If the age gap is more than a few years, be very cautious about it because it can lead to abusive relationships and emotional manipulation, since you will be at very different points in your lives. For a rough idea of how old you should be at least a minimum of half his age and add 7. This is used by many people to figure out ages, for example, a 25-year-old should be dating at minimum someone at least 19-20 years old.
Talk to him. This is the best place to start. If he doesn't know who you are, how can he like you? It can be difficult talking to someone you don't know for the first time, so, just try to become friends with his friends, or start talking to him on Facebook. You could also nudge him when walking past, but make it look like an accident, then apologize and start to converse; however, if he doesn't take the bait, or doesn't seem interested, better luck next time.
Get to know him. Ask him open-ended, interesting questions that yield interesting answers. Boys love talking about themselves, as do we girls. But if you want to get him, you're going to have to sacrifice talking about yourself so much, unless he asks about you. Ask him if he plays any sport, what music he listens to, and his favorite movie. Anything. But the most important thing to remember when having a conversation with any boy, is not to bombard him with an inordinate number of questions, or else he will think you are obsessed with him. Instead, just let the conversation flow.
Hang around him outside of school. Ask him if he wants to go get some ice cream etc. Or if you are to shy/uncomfortable confronting him, ask over text. It's best to do this by indirectly asking. For example, instead of saying, "Hey do you want to hang out at Baskin' Robin?", say something like, "this triple scoop mocha fudge sundae is delicious! It's a shame I don't have someone to share it with so that they could experience its amazing life changing flavor as well". Or you could always use something more subtle, as a hint that you want to hang out. Once you two are together, show him how fun you can be, and don't forget to smile a lot. It makes you seem happier, and guys love happy girls.
Dress in clothes that enhance your appearance. Don't wear clothes that make you feel less confident or hinder your decency. In other words, don't wear clothes that are too revealing, clothes that are too baggy or faded (unless intended), or clothes that are dirty/stained. Instead, wear clothes that you feel comfortable and presentable in. Although you should always keep these in mind, it's important to remember that guys are visual creatures, and crave even the littlest bit of skin. However, to retain the classy, mature look that is key in attracting an older gentleman, you must show skin sparingly. So choose your best body part, whether that be legs, arms, cleavage, etc., and use that as the focal point of your outfit.
Use makeup subtly. Makeup is an irksome subject when it comes to those of the opposite gender because whether they like the all-natural look or cake face really depends on what guy you are talking to. So it all comes down to this: What matches the style you are going for, without being too cake-faced and still being sophisticated and mature enough to woo that older guy of yours? Foundation/tinted moisturizer, blush/bronzer, a little bit of eyeliner or eyeshadow, mascara, and lip gloss works for the experienced makeup wearers, or for a more natural look, you could use blush/bronzer, mascara, and lipgloss, but don't use any unnatural colors that cause you to look similar to a clown.
Be confident. Guys don't like a girl who is insecure about herself and gossips. It gives her an air of meanness. By keeping your head held high, and not caring about what others think about you, makes you seem more mature, and he is more likely to like you because you wouldn't care what people would say about you dating someone older than yourself. If you are confident, it will also be easier to flirt when it comes to time and you seem more mature. A warm smile and eye contact also demonstrate your confidence.
Be yourself. Be genuine and comfortable. Don't act suddenly different and like everything that he likes when you talk to him. Aside from the fact that the conversations become boring due to the fact that all you're doing is agreeing with him, he can see through it. The majority of guys dislike fake girls and automatically are turned off. Be one of the genuine girls in the world; it really makes a difference in you relationship, considering the fact that he will be more comfortable being himself around you too.
Tell him how you feel. Not over IM/Facebook/MSN etc. Do it face-to-face, if you feel comfortable. Tell him that you really like him, and you needed to get it off your chest, or whatever you feel the need to say. Don't tell him you're totally in love with him and obsessed and want to marry him; this will scare him away and he is likely to think that you're creepy. If he doesn't feel the same just smile and say okay! Move on, any guy that doesn't want you is missing out on a lot! There is plenty of other fish in the sea; you just have to find the right one for you!
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