The accidental-on-purpose bump in is a tricky dating skill. You want to put yourself in his path to create an opportunity for conversation, but you don’t want him to know that you set it up ahead of time. The best way to handle your desire to bump into a guy is to be at some of the same places already. When you pursue your genuine interests, you’re most likely to meet potential partners anyway. Figure out what you and your crush have in common, and then make an effort to pursue that interest more actively in the hopes that you’ll be in the same place at the same time.
Ask about his interests. Try to figure out something you have in common. The best way to meet potential dates is to find others who share your hobbies. If he says he’s a big cyclist, ask him where he rides and with whom so you can get an idea of how (and where) he spends his time. If you have never spoken to your crush, you could ask a mutual friend to bring you to an event where he is likely to show up.
Start attending his local hangouts with your friends. Do this only if you’re genuinely interested in the same things: for example, if he goes out to listen to a lot of bluegrass music, and you like bluegrass, too. The more frequently you get out and go to events where he’s likely to make an appearance, the more likely you are to accidentally run into him. And if he doesn’t show up, at least you’ll still be having fun!
Befriend his friends. When you start hanging out in the same social circles, you're likely to see a lot more of each other. Not to mention, if you're able to form genuine friendships with the people who like him, he'll probably find you as trustworthy and interesting as the people he already knows. Even if you start seeing him around and find out that the sparks just don't fly, you're creating opportunities to meet more people and widening your options for potential dates.
Talk to him. Once you spot him across the room at a concert or find yourselves on the same cycling route, you have an instant conversation starter: your mutual enjoyment of the activity at hand. Stand while talking because it removes all barriers between you and the other person, making you seem more open to conversation.