Tempering Great Expectations

In corporate America, men are favored for being confident risk-takers. But in the world of dating, the opposite happens: men tend to be risk-averse—more focused on cutting losses and getting the biggest bang for their buck than growing their romantic investments.

This dating dynamic contrasts my cultural upbringing. Growing up a Filipino in a predominantly Catholic country, courtship ruled our social mores on dating. Men were suitors; women played hard-to-get (pakipot). Kissing on the first date was a taboo, let alone sex. Truth be told, the boys and girls of exclusive Catholic schools would be the first to tell you it’s an expectation, not a rule. Just like Manila’s traffic laws, but I digress.

You can say in a way that the average tech bro or man in finance in America treats dating as safe gambles whereas the men in the country I grew up in approach dating like it’s Sotheby’s. The former weighs the odds of love—sometimes interchanged with lust; the latter bids for love—sometimes confused with lust.

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I am neither here to criticize one over the other nor to make the weary jaded. Instead, this post aims to guide every single immigrant woman from a culture that’s similar to mine:

You can’t play the same rules of dating in America.

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In one of my women’s groups, a woman recently asked how soon was it acceptable to initiate a talk on exclusivity. The question alone raised my eyebrows. It’s always the man who asks, even if our anxiety unalives us.

The other women’s responses were even more disruptive: Three months is too soon. Date more guys (simultaneously). Up to you if you want to have sex—you don’t have to tell the other guy.

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If you’re American, you might ask, ‘What’s that group you’re in?’ Or if Filipino, you might ask, ‘Girl, under which rock have you been hiding?’ Okay, I’m too old for this BS. And yes, I’ve broken the rules in both fields myself.

Nice to meet you, where you been?

The reality is anyone who sells you a dating playbook in America is peddling lies. Just as any game is only as good as the quality of the players, dating is only as good as our matches. Even more so, the quality of the guys we attract is directly proportional to the amount of work we’re willing to put on ourselves—and this goes skin deep.

Expectations wise, it helps to be aware of the cultural nuances between American dating and the place where you’re coming from. Then if you really wish to guard your heart and find dating success, the best thing you can do is to treat dating as an investment in yourself. It’s the only way you can maximize your returns.

“I felt that I owed the deepest gratitude to the best of men.”

Spotting a True Chicagoan

Amid the second snow storm of this season.

There are three ways to tell apart a true Chicagoan:

1. They know that thin crust is the real Chicago pizza, not deep dish. (Okay, this might invite some violent reactions!)

2. They call the downtown Macy’s Marshall Fields.

3. They know what Giardinera is when you ask for it in a restaurant.

But to me, the best way to spot them is in the winter. Chicago ain’t called a windy city for nothing. Those who aren’t from here are quick to discourage transplants like me.

But true Chicagoans are tough. They’re forthright although they practice Midwestern niceties. They don’t downplay the cold; they treat it as a matter of fact. All you got to do is bundle up, they say.

This forthrightness was what emboldened me to pack my bags and leave everything I love in California—year-round great weather included.

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Weathering the Cold as a New Immigrant

Being born in the Middle Eastern desert and raised in the Southeast Asian tropics, I barely survived my first US winter. Just to let you know, we’re not even talking about Chicago winters yet. I was in Bakersfield then where summers were bakin’.

Nonetheless, two things helped me get by: my mom’s winter wardrobe and a great central heating system at my parents’ home where my daughter and I stayed first. Winter clothes can be quite expensive; figuring out styles that are apt and fashionable is another thing. For new immigrants, completing a winter ensemble may take some time.

All the above inspired me to start a traveling shop, Joyful Lifestyles, two years ago. It’s currently dormant as I refocus on my main business.

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Resilience through Resource

One of the books I read this fall was Ilene Smith’s Moving Beyond Trauma: The Roadmap to Healing from Your Past and LIving with Ease and Vitality. For those of us with dysregulated nervous systems because of past traumatic experiences, becoming aware of the resources that we have at our disposal helps activate our sense of safety.

Ilene categorized resources as external and internal. External resources are persons, places, or things that make us feel safe such as a confidante, beloved pet, hiking trail, or teddy bear. (For Chicagoans, this means investing in long puffer jackets and winter boots!)

As an immigrant, I feel fortunate to have my parents as my primary external resources. I did not have to worry about living conditions because they offered my daughter and me a home when I began with no income and credit history. The professional coaching connections I’ve made intentionally while quarantined in Manila during the pandemic also led me to opportunities to earn decently despite a lack of US-issued degree and experience. Lastly, the small business support from my hometown in Bakersfield, as well as some affinity groups opened many doors for me to which I am forever grateful.

Some immigrants may not have the same resources. This why I am taking the time to also write about internal resources. They are the intrinsic qualities that we naturally have and cultivate. For me, I know that I am smart, resilient, and resourceful. I have survived countless hardships and heartaches as a solo parent and an immigrant woman in midlife. I also know that I have a good heart and a sincere disposition toward the good, which helps me forgive myself for my own transgressions. Most of all, I am deeply spiritual—I believe in God who is much larger than my faith.

If you are figuring out your own resources, I’d be happy to be your resource. Feel free to contact me for appointments and inquiries. In the meantime, here’s a tip: Besides listing down what you have and what’s accessible, also make an effort to add and build to what you already have.

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Beauty as a Resource

There’s a special piece of art that had prepared me for what’s beginning to look like Chicago’s coldest and snowiest winter in years.

A kind gesture led to this breathtaking view!

Back in the summer I first visited Chicago, I wandered into the Fine Arts Building and came out changed in ways I shall disclose in later posts. N—, the elevator operator who treated his job like a sacred calling, led me to an unobstructed view of the Chicago Fountain and Lake Michigan, not commonly accessible to both guests and locals.

Am I sentient?

I also met Alyson Lyon, a local artist who understood my comparisons between Chicago and California, and musings about car culture and Jungian transformation. It didn’t take her long to show me one of her private art works—Division and Paulina, two intersecting streets in West Town where I later moved to an AirBNB by happenstance. She painted it on a dreary winter day while also writing about evoking hope through the senses as one leaves behind toxic energies.

This painting now sits at my home office. It has become a sort of lucky charm, expanding my threshold for autumn chills and helping me survive two (pre-)winter storms in a matter of six weeks. Most of all, I held on to the hope it promised in one of my grayest weeks here that only God, myself, and you know.

One day, my healing will be complete.

A ‘Grand Entrance’

After all the peaceful closures I had made in California, I hoped it would be an easy transition to Chicago.

So landing at Midway seemed a wise decision. I did not have to wade through O’hare’s tourist crowds and never-ending hallways with all 41 years of my life in two large suitcases, a handbag, and carry on. Travel light, I kept it to heart.

A typical sight on Lakeshore Drive

Luck was on my side—I got a free Uber Black upgrade with a driver who cheerfully loaded all my bags in his Tesla Model X. I savored the idyllic views of Lake Michicgan as we traversed Lakeshore Drive. Boats sailed while locals ran, biked, and walked with their babies and dogs amid a backdrop of turquoise and aquamarine.

I couldn’t believe this place would be my new home.

Weeks later, a client shared that they found the Chicago crowd the most electrifying!

But my peace was cut short the moment we attempted to enter Montrose: a police car blocked our only entry. Another woman tried to get through, but did not succeed. It’s then that I recalled seeing some Manila connections being in Chicago that weekend. It’s the Chicago Marathon! I couldn’t have chosen a better day to arrive—sarcastically speaking.

Of course, the roads surrounding my apartment were closed. The Uber driver dropped me off at the closest corner. From there, I had push my luggage to get around the neighborhood. They all suddenly felt heavy.

What good fortune I had deteriorated. Because I had to pick up my keys from another building, I needed to get past the crowds—but not without the baggage. The building was more than a mile away. (It’s 2.2 kms for my friends who live in the metric world.)

Give it to my neighborhood, the marathon was also political.

I first approached the corner cafe near my apartment; it did not have the space to secure my belongings. Meanwhile, the shop next door did not want to be accountable. I began feeling defeated, wondering if those responses had to do with my being the odd one out. Then I saw a barber shop ran by immigrants. They willingly took my luggage in, assuring me that they will keep an eye on them. I could take my time.

Thanks to these men who spoke broken English, I finally felt safe and ready to take the keys that would unlock a new chapter.

To be continued…