I rarely paint for people who are not family or paying customers. I think it is awkward. Art is so personal and everyone has their own preferred style. My family has no problem telling me exactly what they like and it’s usually not in line with my own preferred style of art work so I appreciate the honesty. Paying customers will also tell you exactly what they want. Gifting artwork to someone who is not expecting it is a risk. If they don’t like it, they likely feel forced to hang it up anyways and that’s got to suck. I also doubt anyone would openly admit to me if they didn’t like it (other than my family or paying customers). So friends, if you’ve never received a painting from me, this is why!
Not too long ago, I broke my own rule and actually painted a gift painting for someone who I didn’t know all too well for his birthday. It was one of those awkward situations were I’d be on a few dates with this guy, and then it happens to be his birthday. So naturally, I can’t do nothing for it, but then I also don’t want to go overboard since it had only been a few weeks. He’d seen a few of my paintings and particularly liked these two, City Love and After Midnight.