"Are you the one proposing?"

A waiter almost ruined romance

Nov 16, 2023

Hello friends! This is Peregrino, a newsletter about the journey. You’re about to read essay #30 of “40 Before 40,” a memoir I intend to finish before I enter midlife.

Today’s essay is the story of how I proposed to

Diana Cantu

about ten years ago. Since it’s already established that I’m a hopeless romantic, I figured this story would follow nicely.

The previous 29 essays of this series can be found here. If you’re new, welcome! It’s good to have you. And if you are not subscribed yet, I’ll make it really easy for you.

In November 2013, Diana and I had been dating long-distance for nine months. I knew she was the one, and I had bought an engagement ring. All I needed to do was plan how to propose. I knew I wanted her to meet my parents in person before I asked her to marry me, but this was a soft requirement. Still, the opportunity presented itself in the form of my cousin’s wedding.

We flew to Monterrey on November 22nd: Diana from Sacramento via Guadalajara and I from Phoenix via Dallas. Diana was nervous to meet my family, so I prepared a slideshow with pictures of everybody and a short bio of each to reduce the shock. She asked how she would know where to meet me once she landed in Monterrey. I kept telling her to go wherever the Mariachi music was playing—implying that I would hire a Mariachi band to receive her at the airport. She didn’t like that joke as much as I did.

Did I mention that I was anxious about losing the engagement ring while traveling? I had taken the ring out of its box and placed it securely in my jeans’ coin pocket. I didn’t want to risk leaving my backpack somewhere or getting the box with the ring stolen. Or worse, Diana rummaging through my bag and finding it by mistake. My best performance was acting normal when I met her at the airport in Monterrey and pretended I didn’t have an engagement ring on me.

Weddings in Monterrey are big. How big, you ask? In this particular one, the guest count was about five hundred people. The reception hall used to be the biggest kiln of an old steel factory. A twelve-member band was playing, and they would change their outfit depending on the music of the decade they were playing. An open bar, a three-course meal, a snack bar, and chilaquiles were served right before the party ended.

Diana asked me what kind of dress she should wear to the wedding. “I don’t know, the kind of dress you would wear to a wedding,” said I, like an idiot. “Okay, would a cocktail dress be okay? It’s black.” Diana pressed. “Yeah, that should be fine.” Idiot. I should’ve known better or asked my mom or sisters before I answered with the certainty of someone who knows.

We should’ve been clued in when my mom asked Diana, “Would you like me to set up an appointment for hair and makeup for you?” Apparently, I had been living in the US long enough to forget how much women invest in their looks for these kinds of events. Every single woman was wearing long dresses, and their hair was done in a way that looked like they would need to wash their hair several times to remove all the products that made it possible for their manes to be shaped the way they were.

And then there was my girlfriend, the gringa with the cocktail dress, who did her hair and makeup. She still looked amazing, don’t get me wrong. Other women wouldn’t be able to handle a faux pas with half the grace my then-girlfriend did. Eventually, Diana was able to forgive me. Still, let this serve as a cautionary tale for men worldwide: Don’t act like you know everything; be humble, admit when you don’t know something, and ask questions.

Once the wedding was over, and everyone was ranting and raving about “Dianita,” as everyone was calling Diana by then—it is common in Mexico to use a diminutive -ita, -ito, to show affection—the next thing on the agenda was a little excursion I had planned on the 26th.

I had booked a tour of Casa Madero’s vineyard, the oldest winery in the whole Americas. It’s a couple of hours away from Monterrey, perfect for a day trip. The only problem was that the weather had been awful on Sunday and Monday, and there was zero visibility on the highway leading there because of the fog. I was a ball of stress thinking that we would need to cancel.

The plan was to get a tour of the vineyard in a horse-drawn carriage, then have some wine and charcuterie, and finally, I would pop the question. Thankfully, the day we were supposed to go was a beautiful day. Blue skies all the way there with some scattered clouds.

The whole vineyard and winery look from a movie. Imagine an old hacienda with its chapel right as you enter the campus—to the left, a massive building where they produce the wine. To the right the entrance to the hacienda building with gardens, rooms, fountains, and gazebos, all painted white. We found the main office, checked in, and headed to where our tour guide was waiting.

A rugged older man drove us around the vineyard. The vines were pruned and barren since La Vendimia happened a few months prior. La Vendimia is Spanish for the harvest festival. Still, we were the only ones there; we were in a carriage, sharing a blanket and taking all the sights in. We stopped at one end of the vineyard to take pictures, and after our tour guide finished his cigarette, we headed back.

Upon our return, a table and two chairs on a vine-covered patio were supposed to be waiting for us. Instead, there was nothing. I started panicking inside. We headed back to the front office, but no one was there. It was around lunchtime, so it made sense that they were not around. We started walking around the hacienda, taking pictures and killing time while someone came back.

We were by a fountain on a small patio with different rooms facing it. Suddenly, a gentleman wearing black pants, a white chef-looking shirt, and white gloves started walking towards me. “Are you the one proposing?” he shouted in Spanish. I froze. I thought for sure Diana had heard the man. I grabbed him by the arm and walked a few steps away from Diana. “Please lower your voice,” I said with the deepest tone I could reach. He explained that they upgraded us to one of the dining rooms because it was very cold to be outside that day.

Diana swears she didn’t hear the man asking me if I was proposing, but I was sure my cover was blown. The room was fantastic; it had a fireplace, a rustic dining set with a chandelier, and old paintings hanging on the walls. The only problem was our waiter stood in the room the whole time. He poured wine into our cups when needed and tended to the fire while we were there. I didn’t want to be too obvious and ask him to leave the room so I could ask Diana to marry me. I had to improvise.

After we had finished a bottle of wine and were full of charcuterie, we got a tour of the hacienda. We saw several rooms in different buildings, and toward the end, they took us to their meeting room, which used to be a small chapel. An almost life-size painting of St. Rita of Cassia hung on the wall. Diana has a devotion to her, so seeing her friend there was a pleasant surprise. It felt like a wink from God.

The tour was over, and we said goodbye to our guide, and then I saw it. As I mentioned, Casa Madero has its own church in the middle of the campus. We went inside to check this mission-style baroque church. As we walked toward the altar, I saw a statue of the Sacred Heart of Jesus. Guess who has a great devotion to it? Diana. I knew it had to happen this way. We were by ourselves, holding hands, when I got down on one knee, reached for the ring in my coin pocket, and asked Diana to be my wife. Luckily, she said yes.

Diana called every one of the girls who would be part of our wedding party right after that. We bought a bottle of wine that blends Shiraz and Cabernet, our favorite varietals, and we still haven’t opened it. We’re saving it for our tenth wedding anniversary next year. I hope it tastes good. What tasted great was dinner that night. I took Diana to my favorite Argentinian restaurant in Monterrey, and we had great food and more wine.

It's been a decade since Diana and I started planning our life together. Those two had no clue what they were getting into. They were well rested and could pick up and go wherever they wanted. No one told me I was going to witness the birth of my four children from a front-row view or that I would catch vomit on my hands and T-shirt so it wouldn't hit the floor. Yet, here we are. It has been a wild ride, and I can't wait to see what other adventures we’ll get into.