Hopeless Romantic

A letter to my son

Hello friends! This is Peregrino, a newsletter about the journey. You’re about to read essay #29 of “40 Before 40,” a memoir I intend to finish before I enter midlife.

Today’s essay is actually a letter that I thought of writing when

Diana Cantu

told me to be the dad I needed when I was a kid. Our oldest son Oliver has started showing interest in girls, so it felt like the right time to craft this and keep it in the chamber for when the time is right.

The previous 28 essays of this series can be found here. If you’re new here, welcome! It’s good to have you. And if you are not subscribed yet, I’ll make it really easy for you.

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Photo by Leonardo Sanches on Unsplash

My dearest Oliver,

You may look like your mother, but you have my personality. And even though you are just seven right now, I can tell that, just like your daddy, you are a hopeless romantic. There’s nothing wrong with being one. However, I want to give you something that will be helpful in the future. I have been able to learn from other people’s mistakes, so I thought, why not document every single failed romantic attempt of mine? This way, I can point out what went wrong so that you can avoid those mistakes. So when you make mistakes, they’ll be yours only. Buckle up, kid; we’re about to ride on the love rollercoaster.

Too Young

I was in the fifth grade when I first saw her, the prettiest girl in the class. I was infatuated with her, and I couldn’t hide it. One faithful day, something overcame me; I decided it had been long enough, and I needed to know if she would be my girlfriend. I wrote the question on a piece of paper, folded it into a small rectangle, and gave it to her. It was a Friday, and the school day was almost over. After she read my note, she asked if she could think about it over the weekend. I said that was okay. Agony.

Monday took forever to arrive, and I hadn’t thought about the scenario where her answer would be no. I tried to act normal that morning and waited until recess to ask her if she had thought about it. When I followed up with her, she said she had a big headache during the weekend and couldn’t think well. I thought it was unfortunate that she was feeling under the weather that weekend.

My son, that was a polite no. If a girl doesn’t give you a straight answer, she’s most likely not interested. Most importantly, we were in fifth grade and should have been focused on our studies and building friendships with our fellow students, not being romantically involved with them. 

I went to a different school for the sixth grade, so I didn’t know of her for a while. I ran into her when I was in college. It turns out she was dating this goofball I went to middle school with. It made me feel better since, in my head, I placed myself above the goofball in the pecking order. I wished her well and have never seen her since.

Too Soon

In middle school, I developed a crush on a girl I was friends with. We would chat in the classroom and on the school bus regularly. I thought giving her a rose on Valentine's Day would be a good idea. This did not go well. Her response was to walk away while she started crying. Two of her friends went to talk to her while I tried to hide my bright pink face from everyone in the schoolyard.

I don’t know what she may have been going through, but my gesture triggered a reaction I was not expecting. This reinforces my previous point that you should focus on healthy friendships over romantic relationships. You’re probably understanding this better than I did then.

Too Much

I wish I could tell you that High School was easier. It wasn’t. I tried the grand Valentine’s Day gesture two more times. Why? Because I didn’t learn my lesson. One of the girls I gave her a Valentine’s Day present asked me: “Why are you giving me this?” I replied, “Because I like you.” Silence. That, my son, is called unrequited love.

Do you remember that feeling when you talk about that girl from catechism that you think is pretty? Okay, those kinds of feelings will increase with time. It is natural and a part of life. However, sometimes, we must come down from the clouds and put our feet on the ground.

Around this time of my life, I wish your grandfather would’ve explained the concept of vocation to me. You see, I have known for a while that I wanted to be a father. However, I never asked God if that’s what He wanted of me. It will be a great adventure no matter what He calls you to. Now, you can seek His will and yours; if you choose to do your will, you may go through some bumps on the road.

Tom Hansen

I will spare you my college years because there was nothing virtuous about them other than I was able to keep my scholarship and graduate. I got a job, bought a car, and finally made money. I could ask girls out on dates and maybe find the one.

You know your mom and I met on a blind date that Auntie Elissa set up. That’s an example of a good friend looking out for their friend and wanting them to find love. Auntie Elissa saw me helping at Church, Mass, and the Adoration Chapel, got to know me, and then told your mom about me. I was ready to be in a committed relationship.

While living in Monterrey, I occasionally hung out with some theater friends. A girl, who was a dancer, asked me if I would go on a date with a friend of hers. I agreed to go on a date with her friend. I got her phone number and sent her a text message asking her out for coffee. Don’t ask a girl out via text message. Either ask her in person or call her.

When I met her at the coffee shop, I was surprised that she didn’t look like she was a dancer as well. I assumed all of the dancer girl’s friends were dancers. This was not the case. Pro tip: Ask clarifying questions. I immediately knew I didn’t want to build a family with the woman before me. There was no instant physical attraction, but I thought maybe she had a lovely personality.

We went into the coffee shop. I ordered first and paid. Rude. Unacceptable. I was a horrible human being. I wish I could go back in time and let her order first. Then, I would add to the order, whip out my card, and pay for whatever she wanted to eat and drink that night. Always pick up the check on your first date. And on subsequent dates, for that matter. Always let them order first.

“How do you know my friend, the dancer?” I inquired. “Oh, I don’t know her. My friend so-and-so and her are friends. So-and-so gave your dancer friend my number.” A classic friend-of-a-friend move. Notice how I don’t remember the name of my dancer friend; this should tell you that my relationship with her was pretty superficial. This date was kind of a shot in the dark for both parties.

Did she have a lovely personality? In a way. I remember she said she was a pre-k teacher, which is cute. However, when I asked her what her favorite music genre was, she said she didn’t really listen to music—red flag. The conversation didn’t flow very well, and after I finished my coffee and pastry, I said I needed to be somewhere and walked her to her car. I don’t remember if I said I would call her and then didn’t; let’s just say for the purpose of this anti-example that I did. Don’t do that. A “nice to meet you” or “Thank you for hanging out with me” are polite, honest ways of saying goodbye.

In 2009, a movie starring Zooey, “The One That Got Away,” Deschanel, and Joseph Gordon-Levit called “(500) Days of Summer” came out. I was twenty-six at the time. I was a regular Tom Hansen dating all sorts of Summers. Just like Tom’s younger sister, your Tia Lily delivered masterfully the same line a few times: "Just because she likes the same bizzaro crap you do doesn't mean she's your soulmate." And that is the best lesson from that movie.

Well, and the ending. Spoiler Alert: Tom gets his life together, gets over Summer, and meets a girl named Autumn.

The One

I waited twenty-eight years for your mom. I wasn’t ready to meet her two years before that; she probably would not have liked that guy. So, I advise you to work on becoming the best man you can be. Be strong, virtuous, and joyful. But overall, be a man after the heart of God.

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Before you go

I have some questions for you.

1. Are you also a hopeless romantic?

2. Do you trust your friends to set you on blind dates?

3. Is chivalry dead?

4. Are dating apps the worst?

5. Isn’t (500) Days of Summer a great movie? That soundtrack, though.