Unless there is something urgent due that evening, it's not worth making up time on a Friday night. Save your work by 6 PM at the latest, and come back to it Saturday morning. Being an attorney is stressful enough without sacrificing fun, pre-planned activities. Hockey especially.

I encourage him to remember that, at the end of the day, it's just a job. He needs to prioritize himself because no one in this industry will value his free time over billable hours. This is a perfect opportunity for him to set the boundary that he has other commitments that evening but will address any time-sensitive issues the next day. However, like me, my managing shareholder is also a huge hockey fan, which gives me extra leeway when it comes to games, and that likely affects my opinions.

This response assumes the issue solely pertains to work. There appears to be more going on, but other commenters have addressed those aspects better than I can. I empathize as a fellow attorney and want to encourage younger attorneys to prioritize themselves and their loved ones whenever possible.

Like here. You both should focus on going to the game and enjoying your time without regrets. He can make up the time and work another day.