Progressive Corp.’s advertising team met several weeks ago to plan a coming commercial that shows the insurance giant’s pitchwoman, Flo, fleeing a bowling alley to help someone whose car was mangled by a falling basketball hoop.

A debate broke out on the video call over a sensitive issue: Should the characters in the spot be wearing masks?

It is the sort of discussion advertisers are having in 2020. Marketing is about telling consumers a story. For the better part of the year, companies have struggled to determine what story to tell and tone to strike—and whether spending on ads now is even a good idea—amid an unprecedented global health crisis.

Madison Avenue has always been mindful of the nation’s mood, airing patriotic ads during wartime and nostalgic spots with vintage jingles during recessions to remind consumers they have come through bad times before. Being in sync with the national psyche has been especially hard this year, given the unpredictability of the Covid-19 pandemic, anxiety over the coming presidential election and upheaval over racial justice and police brutality.

“It’s a perfect storm of disasters that advertisers have to navigate,” said ad-industry veteran Jeff Goodby, co-founder of Goodby, Silverstein & Partners. “It’s different from anything that has ever come before.”

Some viewers expect to see cues about current events on the screen, such as actors practicing social distancing, while others want to escape from reality, Mr. Goodby said. Brands must figure out when it is right to comfort viewers and when to hard-sell them.

Some companies stuck to inspirational spots during the early days of the pandemic.

General Motors Co.

ran a spot showing a man helping load bundles of hay into a pickup and another man turning on the lights at a Chevy dealership.

Apple Inc.

relied on a montage of