One way to ensure you capture a lot of emotions in your photography is to take a lot of pictures. A Beautiful Mess suggests giving your subject time to warm up in front of the camera and moving around in different ways to allow you to catch a bunch of different views of the subject. Another tip is to get to know your subject so he feels comfortable with you and more connected.
Ways to get to know your subject include telling jokes, asking questions about his life, flirting and just being silly. A subject may display different emotions depending on how he responds to your actions, allowing you to capture his best qualities.
Keep your camera clicking during transitions and in-between moments. Some of the best emotions are caught when people are not aware that you are still shooting. More natural poses are displayed this way, which adds variety to your shoot.
Emotion is often caught naturally when the subject does not know you have your camera ready. When you notice a look on your subject's face, even outside the shoot proper, get your camera out and click.
B & H Foto & Electronics suggests thinking outside of the box, which means taking pictures from angles that you've probably never thought of before. Do not be afraid to focus on a random object, leave heads out of the frame or take a picture from below.