Here's a tip that's worked well for me. Avoid asking "Would you like to hang out sometime?" The reason being that it is easy for the person to say "yes" but nev

Here's a tip that's worked well for me. Avoid asking "Would you like to hang out sometime?" The reason being that it is easy for the person to say "yes" but never act on it. Instead, make it easy to convert their "yes" into an actual activity by arranging the activity before asking them. There are two ways to do this: 1) "Hey, I'm planning on seeing Jurassic Park 3D on Friday, would you like to join me?" 2) "Are you planning on doing anything fun this weekend?" (if they respond with some activity that you're interested in) "Oh, that sounds cool, would it be cool if I tagged along?" Obviously you can replace seeing a movie in option (1) with any interesting activity. The key in both of these cases is that you make sure you have concrete plans to actually do the activity. If they agree, offer to call them to meet up at a convenient time/location.