Article: 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.

What is a summary?
Ask yourself: Find the right place and time to ask him out. Have a date in mind. Have an exit strategy.