What type of tablet? If it's a small one, I'd recommend you starting out on Paint Tool SAI. It's the tool I currently use, and it's smoothing feature helps tons.
Trying out different drawing styles with Paint Tool SAI, here's a Fluttershy :3 Time spent: 15-20 minutes
Edit: Got bored and made a high quality version
Time Spent: around 25 minutes
Don't try and force it on him. Just ignore him about it. I have a friend like this and he made fun of me for about a month, then gave up. Don't fall into his embarrassing remarks or he'll just tease you more.