The context of the following conversation is Jesse selected the item they thought would be best, but they ended up picking the worst possible item somehow.:
Jesse says I went shopping with mom..
The friend responds That is not good..
Jesse responds I picked out the perfect item..
The friend responds What could go wrong?.
Jesse responds Mom liked a different item and you can guess the results - we bought the worst possible item, her choice..
The friend responds Next time, I suggest you go shopping alone..