Here’s a challenge: how do you make a crowd of parents out with their college-aged kids laugh at a stand-up show?

Who’s going to crack up at a raunchy sex joke when their parents are sitting next to them? What about political humor among disagreeing families or social satire when the generation being satirized is just a few feet away?

This was the challenge three stand-up comedians faced at Friday’s Comedy Showcase in Spingold Theater Center, a Fall Fest event. A comedy show whose audience feels too uncomfortable to laugh isn’t much of a comedy show at all, but the way each stand-up tackled the problem seemed instructive of how to bridge this comedic cultural gap.

First up was Luke Thayer. An Illinois native, his act took aim at targets so ingrained in American comedy that anyone could chuckle but not burst into a belly-laugh. His jokes arced around tropes like “men and women act differently” and “old people don’t get social media.” Thayer never made himself the butt of the joke, carefully positioning himself in the “straight man” persona for each story and observation. While he earned some kudos from the younger half of the crowd for a set on others’ racist responses to his interracial marriage, the crowd’s biggest laughs came from an improvised moment: Thayer was a third of the way into his set before realizing the microphone was off the entire time. “So that’s why you guys weren’t laughing!” he chided. “Why didn’t someone tell me?”

Next to the stage was Kiran Deol, who captured the crowd with her natural stage presence and charm. Deol’s act would have killed with an audience of just students, but if Thayer’s hewed too clean, hers leaned too dirty.

Deol employed her Indian-American heritage in several great bits. These included a post-colonial takedown of the UPS slogan (“What can brown do for you?”) and recounting an awkward birthday celebration at an Indian Pizza Hut. But jokes about the bizarre analogies we use to describe women’s pubic hair fell flat on a crowd that did not want to think about sex with their families right nearby.

It was the last act of the night which finally cracked the nut of getting kids and their parents to laugh together. The headliner Myq Kaplan earned huge laughs and applause through a winning three-part formula: keep it smart, keep it dry, keep it fast.

Kaplan carried a home-field advantage. He is a Brandeis alumnus and opened his set with a slew of jokes about — what else? — high tuition costs. This lowered the audience’s guard and let them feel a kinship with Kaplan. The main reason he succeeded was his constant barrage of witty and intelligent jokes, the kind that force the audience into thinking and unpacking the last punch-line just in time for another to land.

Kaplan’s comedy is like a Russian doll-set unstacking then re-stacking itself. He started on a story about an intimidating man in Arkansas, until he mentioned the man told him “L’chaim.” This line directed him onto a set about his Judaism — a big hit with the Brandeis crowd — which pushed him into wordplay about being “straight-ish, white-ish and Jewish.” Then he wound his way back to Jews, then back to the man in Arkansas, all the while peppering his jokes with callback humor to earlier topics so we didn’t get lost in his maze of comedy.

Kaplan acknowledged his deliberately scatterbrained style with the line “one time I was heckled by a lady who just said ‘focus!’” He also spoke at a mile-a-minute rate, forcing the audience to pay that much more attention, which complimented his slightly smug stage persona.

Many of Kaplan’s jokes showed his interest in jokes themselves. He pointed out that more people seem to hate Nickelback than have actually heard a Nickelback song, describing the whole thing as “a reverse ‘Pagliacci the clown.’” Kaplan swung effortlessly between dozens of comedic topics and styles — everything from satirizing gun fanatics to calling an Italian wedding a “marinarriage.” His clever writing, dry persona and rapid-fire delivery ultimately won over the nearly-impossible-to-please crowd at Fall Fest.