This can be unlocked once you unlock the pier area. You'll need to go there, then go back to the Leisure Suite and tell Dick that the pier is a good place for pictures to be taken. He'll say he can't go until his ex leaves.
Take your leftover Barbarian Brew from the beginning of the game and combine it with the bread that you can get by talking to the dudes at the Salon du Lézard (hipster bar).
Then go to the pier again. Use the beer-bread combo on the pigeon to the left of Becky and Lance.
This will trigger a cutscene and this achievement.