Welcome back to 100 Dates in Houston, a dating blog series chronicling my journey to go on 100 dates in Houston, Texas, to find the love of my life. If you’re new here, start with my intro post, explaining the details of this challenge. Today, I conclude my exploration of dating with political differences. This post calls for a bit of a trigger warning as it details an account of transphobia.

Hey friends! It’s time to jump back into part two of my story with MAGAman.  In case you missed part one, here’s a link!

After I challenged him about his position on Nigerian immigrants, MAGAman transitioned the conversation to planning for our date. I knew how I felt about Donald Trump, but I had never considered dating a Trump supporter.  In that moment, I decided to go along for the ride and see what I might learn. 

MAGAman gave me three suggestions for our dinner date. I settled on Chama Guacha, a Brazilian-style steakhouse– the ones where the waiters bring cuts all sorts of meat to the table nonstop until you turn your card over in surrender. 

Chama Guacha

Ya’ll would be proud of me. I arrived at the steakhouse on time – a few minutes before my date.  

Dinner went smoothly for the most part. We talked about our families, work, and favorite pastimes. MAGAman seemed eager to please and asked what my impression of him had been thus far. I tracked that he was polite and easy-going, so I gave him my honest feedback. He admitted that both words were accurate descriptors of him. 

Now, friends, “respectful” is one thing, but “polite” isn’t exactly how I want to describe my spouse. I want him with a lil’ bit of warrior in him. The kind that only surfaces when it comes to his family, loved ones, and purpose. In the words of Jordan Peterson, “it’s better to have a warrior in a garden, than a gardener in a war.” 🤷🏾‍♀️

I asked how his ex-wife might describe him. To his credit, MAGAman was honest.

“She would say I’m too passive.”

But MAGAman’s confession of passivity only confirmed what I had already suspected. He had peppered clues of it throughout the details of his stories about his marriage. I made a mental note.

Willful Ignorance

As we were chatting, an Asian woman approached the table behind us. Her voice was deep, and her facial features were angular. It’s possible she was a transwoman. 

MAGAman took one look at the woman and shook his head in disapproval.

“You know, when I see them,” he whispered, “I think about my daughter and how they want to share bathrooms. I think about her going to the bathroom and one of them being in there and molesting her.” 

“What does one have to do with the other? What you’re talking about is pedophilia. That has nothing to do with being transgender.”

MAGAman tried to defend his position, but he knew his arguments were baseless.   

Rather than storming out of the date, I continued to pick MAGAman’s brain. The therapist in me wanted to understand his thought process to see if I could make sense of any of it.

Long story short, I couldn’t . . .  

We discussed gender issues and abortion laws. Of course, MAGAman agreed with the Supreme Court decision to overturn Rowe Vs. Wade – because women often decide to have abortions without consulting the fathers. He had no comments about absentee fathers or women losing their lives during childbirth. 

The debater in me came out to play for a bit. I asked, “So let’s say a man is totally irresponsible and has baby after baby, year after year, without caring for any of the children. How would you feel about the government putting a law in place for said man to have a vasectomy —you know, for public health reasons? These babies will likely be supported by public dollars and have to grow up fatherless.” 

“No, I would be against that.”

“Why?” I asked with feigned cluelessness.

“Because no one should tell him what to do with his bod—.” MAGAman stopped mid-word. “Ok. Ok. You got me. I see your point.” 

He saw my point, and I saw his limitations. MAGAman was willfully ignorant in matters of gender equality and sexuality. In 2025, with all the information out there, there was no excuse in my mind. 

Weighing the Scales

Despite all that, I went out with MAGAman a second time. I know. I know. 😬 I’m honestly judging myself. 

But here was my issue. MAGAman was so emotionally available. He communicated well. There were no questions about where he stood on me. He was upfront about his past and clear about his future. And his words lined up with his actions. These aren’t easy characteristics to come by.

I weighed the scales and figured one more date would give me clarity.  I wanted to believe that his sound relationship skills might make up for our contrasting values.

But in reality, they could not. 

It all crystallized after date 38 at Activate Games in Katy. I’d suggested the location, thinking that I might be able to explore his fun side, rather than debating politics all night. After ninety minutes of puzzle solving and laser hopping, I was ready to call it a night. 

The Post Date 8

I went home and reviewed the post date eight, an exercise developed by Coach Logan Ury from Later Daters on Netflix.  Rather than sorting through facts and stats after a date, Logan suggests we should ask ourselves eight intuitive questions.

Did he make me laugh? No.

Was I curious about anything? Not really

Did I feel captivated, bored, or something in between? Bored mostly.

Politics aside, the connection just wasn’t there.

Finally, a conversation with my friend, Coach Joyice, helped seal the deal.  I shared the story about the Asian woman at the steakhouse.  As a social worker, I explained I would have been embarrassed to have a spouse carry and express such ignorant views in rooms that I frequent. 

In her wisdom, Joyice broke marital selection in a way I had never considered.

“Your partner/spouse represents your choice, and you need your choice to reflect who you are accurately. ”

I had all the data I needed. There was no way MAGAman could accurately reflect me — especially the feminist and humanist sides of me. 

Sure, he treated me well and seemed ready for a real partnership. I even found him physically attractive. But I didn’t enjoy exploring his mind and was turned off by his way of thinking.  To me, it killed any spark of curiosity or interest. 

And then there was the relationship research. It states that couples with major political differences can survive under just a few conditions.  They must have shared relationship goals, visions, and values that tie them together. In other words, only a strong foundation with real purpose can hold a Trump-Harris household together. MAGAman and I had none of that. 

The verdict

MAGAman could not be my guy. In addition to our political differences, there were other heavy issues I couldn’t overlook during the time we dated. But I had done what I set out to do. I’d remained open and worked through my maximizer ways. I’d given it a good effort.

But who was I kidding? A Trump supporter and pro-Black pseudo feminist? Nah – I knew better.  I have a new deal-breaker to add to the list!

What came up for you when you read this post? Did you already know the verdict before I shared it? As always, if you find value in my little dating memoir, don’t hesitate to tap the “buy me a coffee” button!