Hypothetically, if you had a similar schedule, what would you be doing with your free time?
Sometimes lifestyles will just not be a fit — I went on a few dates with a stand-up comic who had huge stretches of time where he would be doing nothing, and then he’d be on the road for several weeks at a time.
Talk about whether or not going to dinner tonight fits within your budget, for example.
Once you’ve spent some time getting a better feel of how they view the small stuff, gradually increase the depth and scope of the conversation topics to things like big purchases, lifestyles, saving and retirement.
If he’s going to bars every night or playing video games, do either of those activities worry you?