I love this idea, Hillarie. Not only would this be a great conversation-opener, it could result in a finished product (the short essay or padlet) which the student may value for a number of other reasons. It's also offering a way for the student to invite a conversation while being as revealing or reserved as they want/need to be.
I'm thinking that it *could* be a lot of work... If students are not terribly familiar with padlet or technology (searching for images, pasting links etc.) they may find it somewhat intimidating. However, this activity would be very configurable & you could easily reduce the technical requirements if your group felt uneasy.
When were you thinking about trying this?