Who Picks Up the Check?: Talking to Expat Entrepreneur Jesse

who picks up the check in mexico

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In our second interview asking who picks up the check in the lives of singles pursuing financial independence, we talk to Jesse, an expat entrepreneur. Jesse owns his own spa in Ensenada, Mexico. We talk about the difficulties of being FIRE in a small town and dating across cultures. This interview has been edited for clarity and length.

Tell us about your first memories about money. 

When I was 11, my parents divorced. My dad lived nearby. My mom ran the family finances and did all the grocery shopping. She was a big coupon clipper.

I used to play soccer. As a freshman in high school, that was the first time I got real leather shoes. You can get $14 plastic ones from Kmart.

My grandfather was a big saver and investor in the stock market. He liked to read the Wall Street Journal even though he grew up in rural Kentucky and only had a 5th grade education. He was always interested in saving and investing at an early age.

For Christmas we would get gifts, but also twenty individual 1$ bills wadded up in newspaper.  My grandma still gives me a $25 check for my birthday.

What has dating been like for you?

Evangelical and sexually repressed until I was 21. I was studying religion and philosophy at a state school (Wheaton College). I started dating a Catholic girl and I could see that she wanted to stay in Wisconsin and I wanted to go to DC and the relationship ended. Dating for me is about sharing life with someone and making commitments around who you can be emotionally and sexually intimate with.

In DC and San Diego and Guatemala, I was in serial monogomous, and co dependent relationships.  They were normal and just how I thought life was.  When I finished my graduate work in San Diego in economics, and moved to Central America for work, it was after the financial crisis, so there weren’t any jobs. I got used to living in Central America on barely enough to cover my backpacker expenses.

After I graduated with my graduate program, I went to work in Guatemala for two years managing research for one of my professors in San Diego. For 3-4 years I didn’t have a lot of work. I published the paper I was working on and I moved down to Baja to save on rent and to travel. Then I got testicular cancer that was removed. [At the time], there wasn’t any kind of safety net. I had to think about whether I had enough money to take care of emergencies. It wasn’t really until last year that I could see regular income from starting my massage therapy business. I like doing this but I don’t want to be doing this in 10-30 years. I wanted to have options.

[I was basically living in] a retirement community on the ocean. When I got cancer I didn’t want to hang out with retired Americans anymore so I moved to Ensenada and completely integrated into the culture.

In Ensenada, I dated as much as I could. Read as much as I could to understand the social dynamics and manipulation of dating. I’ve pretty much come back full circle but it’s too much hassle to date multiple people. Before, it wasn’t discussed but now people are very clear if we’re dating and if we’re monogamous.

What were your early experiences as an adult with money?

When I lived in DC, I had an ok salary doing consulting. But my feeling when I left was that if I stayed there, I’d have to be making quite a bit more to have enough – to have kids or to get older. It made me miserable to be in an office. I was a nervous wreck. I really needed to have a lifestyle that supported me. And I could only do that when I could control my expenses.

I have my own spa with 3-4 therapists that work under me, working with a lot of tourists.  A lot of people work off the cruise scene. I charge more than average but I also have the ability to speak to tourists.

I was interested in stock investing from my grandfather and in university was president of our finance club during the internet stock boom.  Eventually after studying economics, I took the coursework for CFP and worked with a financial planner as his assistant.  In the end, I am too emotional to do individual stocks (indexing now), and I was not ready to settle down and develop the relationships necessary for financial planning career.  Life sucked for me emotionally at that time, so I had to change.

Where did you learn about dating?

Trial and error. I’ve dated people of many cultures in DC. They were still the same mindset of the working professional.

I was in a relationship with this amazing woman mid-30s veterinarian, but near the end, one of our stopping points was finances. Through a series of conversations I was able to understand exactly what she was looking for – a lifelong partnership where she pays for your clothes and her car but her partner pays for everything else. I did everything to clarify and when I got to clarity I couldn’t’ commit to a serious long-term relationship that would do that.

Two months into it she expected me to pay for the vacation. She wanted me to buy her $100 earrings. 3 days later she breaks up with me because she thought it was awful that I would not pay for the whole thing.

What’s the biggest difference between dating abroad and dating in the U.S.?

In San Diego, my friends are into cuddle parties, which are all about human contact and communication. It’s about [giving and receiving] permission [via] verbal communication about how someone touches you. The same kind of communication skills are taken to the bedroom so people can talk about sexual health or relationship commitments. I got used to being very clear about my expectations and communicating about these things with words.

In Ensenada, people don’t talk about anything – it’s all nonverbal, implied. The women here are not direct at all. It never feels good to be rejected, but you don’t get rejected here – you just get ignored. Or there’s a pretext. I could ask you out for a coffee date tomorrow and you’d stop answering texts two hours before or make up a BS excuse for not doing it. That’s the biggest difference.

In Latin American culture, family is huge. People work Mon-Saturday 2pm. They get Saturday afternoon off and Sunday is hanging out with family. So I pretty much have Saturday night to date someone. Or you spend the time with extended family. With a fairly big family there are frequent birthday party, baptisms, social obligations you have to go do.

I dated a girl who was second generation Mexican in San Diego and I had to manage relationships with her parents, sisters, grandfather. I understand it now but it makes it much more complicated emotionally.

What was your worst date?

When I moved to Ensenada I liked to go to salsa dancing. I invited a woman to go to a flamenco dancing festival. Her parents came. I was at a table with her friends. She went to sit with her parents. She made it clear that I was not allowed to be at the table with her parents. And then she asked to get her bag out of my car and she left with her parents.

Do you think you’ll marry in your new country?

[The main difference of dating in this country] is that this cultural idea of working for the rest of your life is very present. You need a job to be productive and be an upstanding person in society. I’m not opposed to the idea of a long term amazing relationship at all. More and more I see a lot of marriages and people aren’t living happy lives. As I become happier single, that idea of marriage seems less and less attractive. I would like to be the kind of person that supports someone else in whatever they want to do. If they want to be with me, that’s awesome. If not, that’s fine too. Over the decades, your goals change. To feel like it has to be with the same person feels limiting. It doesn’t seem like a reasonable expectation.

But love happens and you just want to be around the same person for as much as you can as long as you can.

Who picks up the check in Mexico?

Pretty much the man picks up the check. I just pick it up. I got into a lot of trouble fighting the culture but these are the rules.

People meet through friends and networks of people. So by the first date you’ve talked 5-6 times and had coffee. The way I do it, I pick things I really want to do so I still have a good time even if the date doesn’t go well.

Recent first dates have been hiking, independent movie theatre/dinner place, steakhouse I wanted to go to, coffee dates for easy exits, beach walking with the dog.

What’s your best piece of advice for dating and money?

Learn to be happy without either. If you’re not needy without anyone else to have someone to watch TV with or cuddle with. Even in my business, when I’m feeling abundant, not needy for another client, I attract higher quality clients and better work. That comes back to personal development whether it comes to spiritual or psychology. The other great thing about here is that I have time to spend time alone, sort through life.

Time is money. FI is the freedom to pursue my own happiness. Getting into a relationship can mean big restrictions on time and money. It’s also control. The relevance of expat dating is that anytime dating involves more restrictions on time and money and options in life that’s exacerbated in cross-cultural situations in outlook of life, demographics in urban/rural.

Anyways I’m going to enjoy the Pacific Ocean, some tacos and an easy life. I like my life. For me, it’s nice to have options.

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