A few weeks ago, when I heard Conan O’Brien was in Havana to shoot an episode of Conan, my heart sank. I’ve always liked him but I’m allergic to the tourist gaze. My many trips to Cuba have taught me how damaging it is. The Cuban regime, like all dictatorships, depends heavily on propaganda and learning it would take center stage on a late night show filled me with dread. Conan promised that his goal in Cuba was to make people laugh, that he wouldn’t touch the complicated politics of the situation. Ay Conan, if it were only that easy.

Because I don’t have cable, I couldn’t watch last night’s broadcast but instead saw the show online this morning, segment by segment. Conan was very kind, self effacing and goofy. He toured the Havana Club rum museum, took a dance class, a Spanish lesson, went grocery shopping, and did a bit at an open air club. He made a ridiculously bad cigar and ate at a famous paladar. He walked along el Malecón and marveled at a view of the city from a rooftop bar. My favorite moments came when he was improvising. He drunkenly turned “Guantanamera” into a Hansel and Gretel love story and attacked his rumba lesson with a gleeful ferocity that would be scary if it weren’t so sweet. Everybody seemed sincerely charmed and seeing my people happy made me happy. But as I clicked through the clips I started to get very uncomfortable.

“His goal in Cuba was to make people laugh, that he wouldn’t touch the complicated politics of the situation. Ay Conan, if it were only that easy.”

You can’t go to Cuba and be apolitical. Traveling there is a political act alone. The brands he joked about at the grocery store were all companies that were appropriated by the Cuban government. That cigar factory he visited was taken from a Cuban family of cigar makers. Cubans cannot afford to eat at paladares because the average Cuban only makes $20 a month, creating an unofficial tourist apartheid where foreigners enjoy Cuba while Cubans endure the regime. The “ruins” that took Conan’s breath away are dilapidated buildings that thousands of people have to live in because they are not free to move out of them without government permission.

Did I expect Conan to go deep? No. That would be unfair of me. He wasn’t there to interview Tania Brugera, a performance artist under house arrest for wanting to place an open mic at the Plaza de la Revolucion for Cuban citizens to express their opinion freely. He wasn’t going to visit artist and performer El Sexto in one of Cuba’s most brutal jails. Also arrested for an intended but not executed performance art piece. He was there to connect with the people. But he was only connecting with the people that work in tourism — which any Cuban will tell you are a small and distinct sector of the population. Even acknowledging that would have been nice, but instead Conan lamented that in a few years there will probably be American stores in colonial Havana. That’s when he lost me.

“I felt I had watched a very friendly stranger go to a party on the third floor of my family’s house, while my family was being held captive in the basement, desperate to escape.”

Why shouldn’t there be a Foot Locker or a Gap in Havana? If Paris can handle multiple Nike stores — I’m pretty sure Havana can too. The idea that commerce would ruin the “ruins” disregards the desperate need for things to change in Cuba. Why shouldn’t Cubans benefit from capitalism the same way Conan does without losing what makes them special? After all, every show clip I clicked on came with an embedded commercial. If Conan really loved the Cuban people as much as he seemed to, why wouldn’t he want the same opportunities for them that have given him such a wonderful platform?

I don’t doubt that Conan’s intentions were sincere. Cubans are awesome. We know how to have fun and have always had a natural kinship with Americans. But by the end of the show I felt I had watched a very friendly stranger go to a party on the third floor of my family’s house, while my family was being held captive in the basement, desperate to escape. I would have loved to have seen him connect with all the floors in that house and not just the ones approved by watchful, very political eyes.