My BF has been giving me a hard time about walking slowly when we go out at night. I explained that I don't want to fall out of my platform pumps and twist or break an ankle. He belittled my argument, so I said I'll bet you couldn't walk any faster than I in these shoes. Instead of conceding the point like a gentleman he said "I'll be I could." My answer was "you are on buster." So here is the bet and where I need suggestions. I agreed to wear the same shoes he wears to insure that I couldn't win the bet by coming up with something silly. His size 9 foot will fit in a large size (10-111) woman's shoe.
Here is my plan. I am buying two tickets to Chicago for the weekend where we can stay with my sister. Web each take only two pairs of shoes: ballet flats with no arch support and heels. Every time he takes the heels off and the flats go on he looses a point unless I do the same. If he looses 3 points I win. We are going to walk go to musems and go dancing. He must start and end the weekend in heels. No deduct for going barefoot through airport security: I can't wait to see him toss his heels in the bin.
Here are the questions: what flat to choose and what heels. I have an Idea that the flats should be pink and very, very feminine so that his wearing them will be humiliating. The heels I am not sure about. Walkable, but the kind that remind you that you arre standing on the ball of your foot after you have been in them a while. Below are some suggestions. The heel would look cute peeking out from his jeans.

If you have any suggestions post them. I welcome ideas on how to bring him to heel.