Artists: When creating a gift for someone, do you make something that you love, or something that you think they'll love?

This Christmas two of my family members have asked for paintings. I did one painting for my sister already, but I wracked my brain for weeks trying to figure out what to paint for her. I was fixated on painting something that said something about her, something that catered to her likes, something that I thought she would like.
The problem is that the final painting looks awful, to me. It struck me as stiff and predictable, flat, even. It reminds me of something you could pick up for $5 on a poster. I hate it, she loves it. (She showed up at my house while it was drying on the table, so it was an accident that she saw it.) She loves it so much that after several minutes of examining it, she was considering a massive tattoo of it on her back.

Now, I am back to brainstorming what to paint for the other person who wants a painting, and I’m stuck. I don’t want to paint something again that I feel is not mine, but I also want to make her something that she will want to hang in her living room (which is what she wants to do.)

So, artists of Fluther, what do you do? What would you do? Would you paint whatever you feel inspired to push out of your brush, or would you try to consider the recipient of the gift?

Help. :\