It’s the season of the long hike, the slow beach stroll, the idle time when you can finally just talk and think for at least a little while. Even if you don’t get to go on vacation over these next two weeks, many workplaces will be quieter than usual, allowing, perhaps, for an early escape and a longer evening meal.

No time like the present, then, to put a few big, searching money questions on the table.

What follows are the seven best queries that I could find that tend to stop people cold and get them to open up about whatever money they have and the emotions that wrap themselves around their personal finances.

You won’t find much about investments below, as it’s easy enough nowadays to put your retirement money in a target-date fund that automates everything or sign up for a cheap bit of software to spread your savings over a collection of index funds.

Instead, the focus here is on family, feelings and the often unknowable future that we have to plan for nevertheless. Scoop out some ice cream or pour an adult beverage and take them in order.