Two weeks back, my best friend's dad was in town. He was kind enough to take myself and several of my close friends out to dinner. We joked and made small talk as we put in our drinks and appetizers. Eventually my best friend's dad––"Father Rob" as he is affectionally called by us boys––posed a question to the table. "Okay, so how is everyone really doing?"

It was silent for a moment as the entire table felt very vulnerable––as if we were asked to strip naked and make a lap around the restaurant––but then someone spoke up. "I've been struggling to be honest––tomorrow is the ten year anniversary of my best friend's passing."

I had no idea. Neither did anyone else at the table.

Over the next two to three hours, we each gave our answer to Father Rob's question. By the end of the night, I was overcome with the realization that sometimes the people who we are closest with are the people we know the least.

I love the question, "How are you really doing?" Because it elicits a deeper response than just simply, "I'm doing well." Furthermore, it's a five-word mantra that can remind us to go deeper with our parents, our siblings and our friends.

Because unless we ask, we can never truly know how someone is really doing.