I’m impressed that you are interested in dealing with this head on. Being able to appropriately express feelings is an important social skill. It lets other people in on how you are responding to a situation so that they can then know how to respond to you. You do have feelings. You just need to develop more comfort in showing them. My guess is that you grew up in a family that was in some way inhibited or where showing feelings wasn’t permitted. We have to help you learn now what you should have learned as a kid.
In Alcoholics Anonymous, they have a saying: “Fake it ’til you make it.” The idea is that if you act sober, you will eventually become sober. It can be equally helpful in learning how to be a more emotional guy. If you act like you are comfortable expressing your emotional side, pretty soon you will be.
Here’s what I suggest to people with a similar issue when I see them in my office: Think of a person you know who you think does a good job with showing emotion. Sit like the person. (Yes. I know this can feel silly but it really does work. Bear with me.) Now stand like him. Walk around the room, pretending to be him.
Now think of some situations that might require sharing some expression of feeling. What would that person do? How would he change his body? His face? What would he say? (Can’t think of a real person? Think instead about a character in a movie who you would like to imitate.)
Try out many different kinds of feelings. Do this exercise as “homework” every day for a few weeks. When an opportunity comes up that you think requires some sharing of feeling, act as if you are that person. Do this faithfully for a few months and your body and mind will begin to do it automatically.
I wish you well.