This is my attempt of dating in cuba without paying:
As soon as I got off the plane, it hit me—I was back in the Dominican Republic. That feeling stuck with me until I stepped outside the airport and laid eyes on the cars. They were so old, like I had stumbled into a time machine. I hopped into a taxi and headed to my AirBNB, replaying what I’d heard about how tough it was to hook up with Cuban women. They said it was nearly impossible unless you were willing to pay.
By now, most of my readers know I don’t pay for sex. I might cover the cost of a taxi or dinner, but not for sex. My mission in Cuba was clear: spend a week there, get laid, and have the girl like me enough that money never even comes up. That was the plan, at least. Maybe the rumors about Cuban women only wanting money were exaggerated. Only time would tell.
The first challenge? I was staying in Vedado, Havana’s second most touristy spot, right after Havana Vieja. But I had a whole week, so no need to rush. I spent the first few days just exploring. I must’ve walked 20 miles in those first few days. Havana is stunning, a true architectural beauty—Latin America’s time machine. Kids played in the streets, and teenagers hung out along the boardwalk, El Malecon. I hadn’t seen so many people outside like that since my childhood. Video games and the internet haven’t taken over here just yet.
A few days in, I still hadn’t made a single move. I should have, because I caught a few signals of interest during my walks. But, it seemed like I got fewer in Cuba than in Colombia or the Dominican Republic, the two places I visited before Cuba. Maybe it was because of all the tourists flooding Havana.
Daygame in cuba
But then I decided, enough was enough. Cuba’s a tourist spot, but it’s got this magical vibe. By the third day, I made up my mind—it was time to try to get laid. I tried a few approaches of daygame, but the girls got all nervous when I talked to them. They’d glance around, checking if neighbors or friends were watching. It felt like there was this stigma against foreigners among regular Cuban girls.
During one of my attempts, I met a Cuban guy in his 40s. He loved talking about his two girlfriends and his adventures chasing women. He confirmed what I’d heard: “Cubanas siempre piden dinero—Cuban girls always ask for money.” He said it like it was a fact, like it was the most obvious thing in the world. My mission might be harder than I thought.
Clubbing in cuba
So after some failed daytime attempts, I hit the clubs that night. I was alone, but I’d gone out alone before. Life would’ve been so much easier if online dating worked in Cuba. I’m pretty sure Tinder’s banned there. The hour of internet I could buy each day from a hotel lobby would’ve been enough to set up some dates. And honestly, I’ve gotten ridiculously good at online dating. Efficient, even.
This is why I love to travel. It forces you out of your comfort zone, whether you like it or not. For me, every time I get pushed out of that zone, I end up happier in the end. It’s what life’s all about—challenging yourself. I can’t keep ordering girls like pizza in the Philippines forever.
I got to the club early and managed to snag a table without buying a bottle. I was in Cuba, so of course, I drank rum and mojitos. On my second drink, as the club started to fill up, a gay guy struck up a conversation with me. Over the years, I’ve learned that gay guys make the best wingmen. Where a female friend might warn a girl not to be a slut, a gay friend will say something like, “If you don’t fuck him, I will.”
Mexican girls in cuba?
So, when I spotted some cute girls in his group, I dove into the conversation. Two minutes later, he introduced me to the cutest girl in the group—a Mexican girl in Havana for work. We started talking, and she mentioned they were heading to the beach the next day. She invited me along, which was perfect because I had no one to do stuff like that with.
I spent the rest of the night with them. The Mexican girl was cute, and I really wanted someone to go to the beach with. There was another girl at the club who caught my eye, but I didn’t want to mess up my chances with the Mexican girl. Then, the Mexican girl found me, telling me her gay friend got kicked out of the club for mooning some people. I guess that’s one downside of having a gay friend.
Finding a fit cuban
I saw my chance. I told her I’d meet them outside and went to find the girl who caught my eye. She was a Cuban girl, an athlete. I got her number and headed outside.
I tried to get the Mexican girl to come back to my AirBNB that night, but since we were leaving early for the beach, it complicated things. One of the girls in the group was a local Cuban, and we ended up crashing at her ghetto apartment on the outskirts of town.
Having just spent months in Colombia, I couldn’t help but think how risky it was to go into a ghetto with people I barely knew. But from what I’d seen, Cuba was different. People walked around with their cell phones out, and Cuban guys had no problem talking to strangers. In my experience, it takes a very safe community for things like that to happen. Despite what you hear about Cuba in the U.S., I was in the safest country in Latin America.
I was too drunk that night to sleep with her, but I woke up next to the Mexican girl on a mattress that looked as old as the cars in the streets. She was only wearing sexy pink and purple panties. It wasn’t hard to get them off, and I had my first notch of the trip.
But then I wondered—does a Mexican girl even count? She was just another tourist, like me. She counted as a notch, sure, but she didn’t bring me any closer to my mission of sleeping with a Cuban girl without paying for it.
The AirBNB host had a cell phone for guests to use, which was a lifesaver since communication in Cuba can be tricky. I messaged the Cuban athlete girl from the night before and went to sleep.
The next day, she responded, and we made plans to meet later at the park. She was a cutie, and thank God I spoke Spanish because she didn’t know a word of English. She had a big ass and legs like a racehorse. She was a sprinter, aiming to make the Cuban Olympic team.
I used the heat as an excuse to get her back to my place. “Tengo aire en mi casa, no estoy acostumbrado al calor—I have air conditioning at my place, I’m not used to the heat.” It was a white lie. I’d just come from the hottest city in Colombia, Santa Marta. But it worked like a charm.
An hour later, I was inside her, my second notch in Cuba. It was a relief, and the sex was great. Afterward, I waited. This was the moment—Cuban women are famous for asking for money. This was when it would happen.
I turned on the charm, made her laugh, and hoped I wouldn’t hear those words. We talked for another hour until she said she had to leave. I walked her back to where we’d met, always expecting some excuse about needing money. But it never came. As she walked away, a huge smile spread across my face. Mission accomplished.
How hard are cuban women?
After a week in Cuba, I wouldn’t call myself an expert, but I’d say Cuban women are similar to Mexican women. They’re not the hottest in Latin America, more like average. They’re not the easiest or the hardest, just average. If you go to Cuba, try to get laid, but don’t make it your main reason for going. Go for the culture, the Cuban cigars, the salsa, the mojitos, and the rum. Go to catch a glimpse of how the world lived 50 years ago. To see the amazing architecture and beaches with water so blue you’ll think your eyes are playing tricks on you.
