On the gift-giving spectrum of "easy-peasy" to "deep thinking", my husband leans heavily to the "deep thinking" side of the scale. Basically, this means that walking into a retail store is virtually impossible (unless it's Kiosk) when I need to get him a present.
This past Hanukkah, I had this amazing illustrated family portrait made by the uber-talented (old college friend of mine) Alessandra Olanow. I emailed her a bunch of photos of the four of us, and she interpreted them (with a few back and forth questions) into singular portraits. I absolutely love the way it came out!
(In case you are wondering, "watermelon" is something Michael and I used to say to each other in our early dating days. I wanted the drawing to feel like a gift from me to him, so I had Alessandra add the talk bubble.) Here is Alessandra's portfolio site in case you want to see more of her work.