For most VWP users on arrival, the CBP doesn't commonly ask an employment question. CBP asks it often enough but not of everyone; it's not even asked of most IME. And when it's a family with young children in tow, the question of employment seems to become even less likely from what I've seen at US POEs.

It's the VWP-using traveler by himself/herself who is more likely to be asked such questions than a VWP-using couple presenting themselves together or as a family with other dependents in tow.

Taking an unemployed boyfriend/girlfriend for vacation to the US is commonly not a problem; and if the unemployment status is a product of a health issue and the person has health insurance coverage/related repatriation coverage for the duration of the US visit, then it's unlikely to be a problem in and of itself. People taking a sick, unemployed relative or other loved one for vacation to Florida/California/Disney for a possible once in a life trip is anything but unheard of at US POEs.