NHL 14

While playing through the Be A Pro seasons, you will get invited out with teammates at least 5 times each seaso. It usually occurs when you team has 3 or more days off in a row and it doesn't matter how you respond to being invited out, you still get the achievement.

You'll get this shortly after making it into the NHL in any way by playing LIVE THE LIFE (aka Career, Be a Pro). So when you start off just make sure you pick the answers that sucks up to management and your teammates and you'll get this in no time. Just simulate if you wish until an OFF-ICE event comes up and afterwards it will pop.