Red Vs. Blue: My Experience Dating a Trump Supporter

Apr 3, 2025 | Culture, Dating | 2 comments

Date #35 was my final of 2024.  I began losing steam after being ghosted and zombied for my last three dates.  I had mixed feelings about turning forty and was starting what would become the worst job of my entire life. It all resulted in a four-month dating hiatus. 

It hadn’t been intentional.  With my practice and full-time job, I worked thirteen-hour days. I was exhausted all the time and missed the freedom of business ownership.  There was little time for fun or play. 

Dating CANNOT be the only source of excitement or happiness in a woman’s life. It’s a setup for failure and adds too much pressure to an already challenging game. Dating requires time, space, and positive energy to make the best connections. At the time, I had none of that.  My boss stressed me out on the daily – I had no desire to allow someone’s son to do the same. 

So I benched myself for almost four months. No apps. No mix and mingle events – just focusing on my goals. I made a plan to leave the job in January.  Then, I would return to my real life (and 100 dates).

Summer transitioned to fall, and the blazing Houston summer temperatures cooled.  September, October, and November passed – no dates.

And then – at a holiday party in December – I met the man who would bring me back in the game.

Here’s our story.

Date #36

After our meeting at the holiday party, Date 36 texted me the next day.

“Just wanna say thanks for giving me the audience last night. It was nice talking with you. I would like to have a chat with you again.”

Giving him the audience? I thought to myself.  Who talks like that? Not most American men.  

If you’re assuming Date 36 was foreign, you would be correct – Nigerian to be exact.

Our first phone call lasted over an hour. He was easy-going and a good communicator. He openly shared he was a divorcee and in his forties. 

His age was a shock to me. Date 36 had all his hair, was in good shape, and looked well hydrated. No shade, but many men in their forties cannot check all of those boxes.  Alot of them look like they’ve been through it. 🤷🏾‍♀️  It’s becoming a problem for me on the apps. I don’t mind matching with men my age and higher, but do they all have to look like paw-paw?

And I’m not alone in these sentiments. I recently came across a reel describing what I’ve noticed these past few years.

Someone, please tell me what is happening with the men?

Ok. Back to Date 36.

Early in our conversation, he shared that he was a father to three children.  😬 I’m not gon’ hold you –  three children is a lot for me. In the past, it would have been a deal-breaker.  It’s not that I don’t like children – I enjoy them.  The issue is that these men typically fall into two categories. Category A has little time and flexibility to date in the way I like because they are busy being good fathers.  Category B fathers have no issues with time and flexibility because they never see their children – yuck.  

But just before meeting Date 36, I had decided to take a different approach to men with children. Rather than putting them all in a box, I would judge each by his actions.  Perhaps there was a way a man could be both an active father and available to me in a way that felt right. I would remain open and see where it took me.

HOW TO NOT DIE ALONE

My newfound openness was prompted by new dating research I came across after watching the Netflix series “Later Daters” and googling the show’s dating coach, Logan Ury. In her book, How to Not Die Alone, Logan states three dating tendencies can render people single: maximizing, hesitating, and romanticizing. Always eager to learn, I visited Logan’s website, took her Dating Tendencies Test, and discovered I may be a “maximizer.” Maximizers have unrealistic expectations of their partners and obsess over making the best possible decision. Feel free to take the test yourself and share your results in the comments.

Logan suggests maximizers consider that there are many possible people with whom they can build a great relationship and that there is no perfect person. To me, this translated into being more open and flexible. 

relationship guys

Date 36 and I chatted for a few weeks while I visited home for the holidays. He was no relationship rookie. His marriage had lasted over a decade. As we talked, I gathered that he was what I’ve termed a “relationship guy”. 

Relationship guys are men who do commitment well. They don’t run from it, but towards it. They enjoy being in relationships and are emotionally available. Relationship guys communicate well and desire a partner for companionship. As such, most are already locked down by their thirties. 

I liked that Date 36 seemed to be a relationship guy. I liked that he was clear in his actions and communicated well.  Three kids were a lot, but I wanted to experiment with being more open. 

THE GRAND REVEAL

And then he dropped a bomb on me. 

The night before our first date, as we talked and made plans, Date 36 revealed that he was a Trump supporter and had voted for him in the last election.

RECORD SCRATCH

Sir what?  

Not to step on toes, but friends, I struggle to wrap my mind around Black MAGA supporters.  I know they exist. I even know a few personally. And try as I might, no matter how many hours of debate and intellectual discourse we log, they will never make sense to me. They all seem to possess a cognitive dissonance I can never see past. 

A Country Divided

Yet at the same time, I have an unpopular opinion regarding US politics. In the past nine years, we’ve become far too divided as a country. 

In my hippie granola social work professional circle, if someone so much as hints at supporting a Trump initiative, they are nearly eaten alive. The same goes for my super pro Black personal circle. Without listening for perspective, we are judging, shaming, and even hating one another. Family members are no longer speaking, and thirty-year friendships have been obliterated – all due to political differences. It’s a recipe for civil war. 

I refuse to give Donald Trump that type of power over my life. 

Unlike many, I believe a friendship can survive political differences. It doesn’t happen often, and it might sound like a delusion, but I stand on it. With respect, love, and shared purpose, a Lib and a Trumper can coexist within a close relationship. 

Last year, I shared this perspective and my personal experience with Trump supporters on Real Talk Friend Therapy, a podcast about friendship. Check out my episode

So if friendship is possible, what about romantic relationships?

I didn’t know this man was a MAGA supporter when I met him.  If I had, I probably wouldn’t have exchanged numbers with him. But I’m glad I did. I was able to explore an interesting question in partner selection. Can two people on opposite ends of the political spectrum make it work?🤔

Why trump?

During our phone call the night of his big reveal, MAGAman (I’ve been waiting to drop his pseudonym on y’all) explained his support for Donald Trump. Although an immigrant himself (naturalized by his ex), MAGAman supported Trump’s immigration policy. He believed immigrants needed to do things ‘the right way” as he had. He talked and I winced as he referred to immigrants as “these people”.

Then, I checked for his cognitive dissonance. 

“So, you’re Nigerian. You know some Nigerians come here through marriage and various legal means, while others fight for their lives to come here by any means necessary. You know the extreme poverty many are trying to escape in your home country. And with that knowledge, you believe all those Nigerians should return to Nigeria?”

“I believe that people should abide by the law,” MAGAman dodged the question. His cognitive dissonance reared its head. 

“I need a yes or no answer, sir,” I challenged him. 

MAGAman struggled. I could hear his uneasiness through the phone. Eventually, he gave in.

“Yes, they should return and go through the legal process.”

He had stood his ground and cleared his dissonance. But, in my mind, he had also betrayed his people. I didn’t react. Nor did I argue with him. It wasn’t my job to convince MAGAman of anything. 

He went on to explain additional reasons for his support of Donald Trump.  As he talked, I listened. MAGAman wasn’t an extremist like other minority Trump supporters I’ve encountered.  He didn’t agree with all of the tactics and shenanigans of the administration, but he still felt it was the best option for our country.  

I still didn’t like any of it. 

But I had already committed to the date. Did I want to be so dramatic and close-minded as to call everything off right then and there? Being a Trump supporter had not been one of my dealbreakers at the time – I had never even considered it.  Naively, I never thought I would have to. But there I was, entertaining a Black immigrant man who wanted to Make America Great Again.  

As we talked, I wondered if solid relationship skills could outweigh political differences. His opinion on how to fix the economy would not directly impact how MAGAman might treat me as a partner, would it? What was most important to me was that a man valued me, treated me well, and shared my relationship goals. Did political affiliation have to be an issue?

We would soon see.

Check back next week to see how date #36 unfolded!

Kaity Rodriguez logo

P.S.  Did you know that I wrote a journal? I created The Confidence Project Journal for self-reflective women who love journaling and luxury experiences. The luxury VIP package includes 52 journal prompts, a signature gold pen, a gold metal bookmark, a confidence playlist, and souvenir packaging.  Click here to purchase your copy!

2 Comments

  1. Tami

    I took Logan’s test before, but I can’t quite remember the results but knowing me I’m probably the hesitator ! LOL
    Ever since Trump’s first term I could and will never date someone who supports him. Trump is an outlier! He is NOT politics as usual AT ALL and is way BEYOND conservative vs. liberal! I have yet to hear anyone who supports him, make it make sense. And the few who know better, usually only support him for their own selfish motives and greed. The fact he is an immigrant and referring to other immigrants as “these people” would be the dealbreaker for me. Trump supporter love him because of how he will handle that one issue they hate most, dismissing all the other harmful things he’ll do, I honestly don’t see how anyone who supports him would align in my values or even treat me well.. I’ll wait with anticipation to see if your experience with MAGAMAN disproves my theory that Trump supporters couldn’t possibly make good partners, unless you are a right wing , Christian conservative , traditional family values, stand by your man, submissive woman.

    Reply
  2. CJ

    Congrats on the open-mindedness!… most Nigerian men, whether in the States or back at home, would rather a Trump presidency than Biden or Harris.

    I do not believe a vote for President should determine compatibility… imagine being married for 20 years and then disagreeing; should there be a divorce?

    I’m also glad you’re back in the entrepreneur world and writing about your experiences

    Reply

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