Last year, when CVS called Ian Goldstein and told him that he owed $23,000 for medicine he takes for Crohn’s disease, he spiraled in despair. After a fruitless call with the pharmacy, Mr. Goldstein, a comedian and writer who lives in Brooklyn, N.Y., went for a walk to clear his head and had to sit down.

“I went into a complete panic state,” Mr. Goldstein, 32, said. He had become used to wrangling with health care companies over billing mistakes and coverage ever since he was diagnosed with the condition as a teenager.

Still, the need for constant vigilance exhausts him. “There’s always some clerical error that blocks the whole thing up,” he said. Mr. Goldstein only managed to resolve the matter with CVS after months of calling the pharmacy three times a week.

This year, after he hit his insurance deductible, he decided to celebrate by throwing a party. On a sweltering Sunday in June, Mr. Goldstein and approximately 60 guests gathered at the Brooklyn Art Haus, a performance space in Williamsburg co-owned by a friend, for an evening of camaraderie and storytelling.

“Health care is such a problem, I just felt like celebrating that I’ll get to pay less money now,” he said.