As it goes with the rest of your body, you can literally train your smile to become better. One of the go-to exercises to make this happen is by stretching your mouth. Done repeatedly over time, this will make your mouth more limber and ready for expression. First off, stretch the corners of your mouth to the sides. Keep your lips together while you do this, and hold for 10 seconds per rep. After your 10 second hold, open your mouth to expose the fronts of your teeth. Hold for another 10 seconds. Open your mouth further to the point where about half of your teeth are showing. Hold for another 10 seconds. You can repeat the steps in reverse to close the smile back down gradually. A full rep of this exercise will take about a minute, and can be repeated as many times as you like. Everyone should know that a smile is more than teeth and a mouth; it's got to do with the whole face. Smile lines are a natural result of age. Luckily, they can be reduced with this simple exercise. Pucker up your lips as though you were about to kiss someone. Next, holding that position, try to smile as much as you can. Hold it until you can feel an ache around your mouth. This will mean that the muscles are responding to your exercise. It's recommended you only do this exercise once per day, in order to prevent straining the muscles of your face. You cheeks cannot be underestimated when it comes to forming a smile. Cheeks influence the control you have over your smile. To start, smile as widely as you can while keeping your lips closed. Holding this close-lipped, ear-to-ear grin, try to wiggle your nose around for at least 5 seconds. Repeat this easy exercise 10 times in a row. All told, it shouldn't take more than a minute to do all of it. Because these mouth exercises are fairly easy to do, there's no reason why you shouldn't be able to work them into a morning routine. Given that the faces you'll make will be fairly silly, it's probably something you'll want to do while you're still in bed or in the shower. Nonetheless, for the best effects, you should try to remember to follow through with these exercises at least once per day. Remember to look at your smile regularly as well. You won't be able to see any difference if you're not taking some time to look at the very thing you're trying to improve upon. If you mean to train your body to do something, it stands to reason you should do a lot of it. Making a frequent habit of smiling will help improve your smile in a lot of ways. For starters, the muscles you use to smile will be put to use. More importantly however, if you make a regular habit of smiling, it will come more naturally to you. Even if you have to fake it until you make it at the start, you'll eventually find yourself smiling a lot more than you first thought possible. If you're just smiling by yourself, try giving yourself the widest smile possible to maximize the effects of the exercise.
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One-sentence summary -- Stretch your smile. Erase smile lines with a pursed smile. Exercise your cheek muscles. Commit to a regular exercise routine. Smile often.

What's the worst thing that can happen? The worst thing that can happen would be that he will respectfully say "no" if he is a decent person. Keep this in mind and then prepare yourself to ask him out. Remember this will help you endure the pain in case this happens. Make the opportunity to ask him in a casual, low-pressure setting. It might be in the hallway, at the water fountain, on a sports field after practice, or wherever else you usually see him. Pick an isolated place, as well as a time when he is likely to be relaxed. Here are some things to keep in mind when you choose the right time and place: Get a little privacy. You do not have to be completely alone, but you will both probably be more comfortable if you can do the actual asking in a semi-private space. People may not respond honestly when their friends are hanging around and they feel pressured, so some privacy can help you get a real answer. Do not make a big deal about pouncing on the first available second of alone time. If you're both together in a group, lower your voice to half volume and say, "Hey, could I talk to you alone for a second?" and walk a few paces away. Do not give off creepy vibes. Things like silently standing in front of his locker every morning, calling him then hanging up over and over, or constantly asking other people about him may come off as creepy--and something a stalker may do. Give your crush some space. Do not follow him around in real life or on-line. A little recon is fine, but following his every move gets into an unhealthy obsession. Pick a time and place that makes sense. Asking him out after drama rehearsal may be perfect, a 1:30 a.m. text may not be. If it's your first time asking this guy out, you'll be a lot more confident if you invite him to a specific activity. It spares you the stress of coming up with something to do while you're on the actual date, and won't leave you saying "Uhhh... I don't know" when he asks what the plan is. Here are some ideas to get you started: Don't think too hard about negative thoughts like 'he will laugh at me', 'he will reject me', 'he will friend-zone me' etc. Remember that guys feel and think the same way when they approach a girl which is the main reason why so many guys exist in the so-called 'friend-zone'. The truth is you will find out only after asking, muster up some courage, ask him out. You can do it! You may be surprised to find how they would react as most guys are quite easy to talk to as compared to girls. Plan a classic date. There are some tried-and-true activities to do together for dates: Dinner: at a restaurant, or at home with takeout, or something you made. Activity: seeing a movie, going to a concert or show, visiting a museum, comic book convention, a hike, a baseball game or another interest you two have in common. Pick something that specifically appeals to your target date. Sometimes you may not sure if you share common interests, or you are not sure if you like something he likes. Find out what he enjoys, and give it a try. Very often this is a great way to show you are really interested in finding out more about what he likes, and willing to try something new for his sake! Though you should focus on the best case scenario (a resounding yes!) instead of the worst, you do need to be aware that there's a teeny-tiny chance that the guy won't say yes. Maybe he likes someone else, or maybe he was startled and only thought of you as a friend -- either way, you'll get through it. But if you want to make the most of the situation and not lose your cool, you should come up with a Plan B in case things don't go as planned. Come up with a reason to leave in advance. Whether it's saying that you have to study for a test, get to your next class, or that you're late to meet up with a friend, it'll sound better if you've prepared it. Come up with something else to ask in case you can tell he's not feeling it. If you approach him and he's clearly not in the mood to get asked out, think of something else you can ask him so it doesn't look weird that you came up to him -- ask for the math homework or if he knows when the home baseball team is playing that day.
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One-sentence summary --
Ask yourself: Find the right place and time to ask him out. Have a date in mind. Have an exit strategy.