Welcome back to 100 Dates in Houston, a dating blog series chronicling my journey as a thirty-something woman on a quest to go on100 dates in Houston, Texas to find the love of my life. In this post, I share my experience stepping outside of “my box”. If you’re new here, start with my intro post, explaining the details of this challenge. Enjoy!
Hey, hey, my loves! I know– it’s been a while since my last update. Please bear with me. So much is happening in life!
For starters, I turned forty! I threw myself a little Hawaiian-themed pool party to celebrate the occasion. Take a look!
It still amazes me how I’ve been able to move to a new city without the built-in support of family or a job. And yet, in just over a year, I’ve managed to build a solid support system of people who care about me. Ain’t God faithful!
In addition to running my therapy practice, I’ve also started a new job to help fund projects for my home. I work from sun up to sun down, ya’ll. 😭
Perhaps what surprises me the most is that despite working twelve-hour days, somehow I still find time to date, work out, and see friends. We make time for what we want, right? Although I’m taking a break from the apps, I’ve had dates lined up for the past few weekends. I even had a little weekend trip to New Orleans for beignets and gumbo with Blasian Bae – more on that some other time. 🙃
Although I’m crazy busy (and often exhausted), I’m happy because I’m working on my goals and making my own way. I think that’s the secret twenty-five-year-old me needed to know. She would be proud. Forty looks good on me!
So, let’s jump back into these 100 dates, shall we? Have you missed me?
The winning strategy wins again
Remember the Facebook group post that almost compromised my second date with The Italian?
In case you forgot, here it is again:
See that winning formula? I asked a question relevant to the group, selected one of my cutest photos, and threw in a little flirtation to let the group know I was single. Within minutes, the messages began to pour into my DM’s. Two of those messages would become dates 25 and 26.
Date #25
Following my Afro-beats post, I received a message from a familiar face. I’ll refer to date 25 as “Sky Guy” because he loves anything aviation-related.
The message he sent me that day hadn’t been his first. Months before, Sky Guy responded to a post I’d made in the same group. While he expressed interest in taking me out, he was concerned about being a part of my 100-dates experiment and worried that people may be able to identify him publicly. His message was lengthy, thorough, and well thought out – but honestly, a bit intense for a first message.
I don’t always respond to DM’s from strangers when I’m not interested, but something about his message compelled me to reply. Even through the invisible barrier of technology, this man seemed genuine and thoughtful. I didn’t want to leave him hanging.
I declined a date with Sky Guy back then because of his trepidation about my approach to dating. And then there was the fact that he appeared quite a bit older than me – ya’ll know I like ‘em young and spry! I want my partner to be comfortable and confident knowing I write about my life experiences. This blog is my baby – it comes with the package.
The follow-up game
A few months later, in February, Sky Guy circled back to my DMs. This time, he only said hello and wished me a Happy Valentine’s Day. I found it sweet that he’d reached out just to say he’d been thinking of me.
Finally, just a short while following my date with the Italian, Sky Guy made his way to my DM’s for a third time.
“Our paths are crossing again in the ____ group. I still like you. I would like to do coffee with you and see if we might have a boo future.”
“Boo future?” I had never heard it put quite that way.
Although I don’t subscribe to the “make ’em chase you” approach to dating, I do appreciate it when a man is serious, intentional, and genuinely interested in me. It’s my dream to one day be one of those women who can confidently boast and say “My husband don’t play about me.” So, nonchalance simply won’t do.
Sky Guy seemed serious. I could also tell from his group activity that he was grounded, intelligent, and respectful. What could be the harm in one coffee date?
“Hi ________. Why not? You’ve been so sweet so far. Any chance you’re free tomorrow afternoon?”
brass tacks
Within two hours, Sky Guy replied with a list of four different coffee houses to choose from. Options and effort! Ok, sir! I see you!
After viewing his list, I settled on Brass Tacks. Their menu was the most robust and varied. We agreed to meet at 3 pm.
The next day, my date arrived early at the coffee shop. He sent me a message informing me of my parking options and offered me his spot when I arrived — automatic extra points for being a gentleman!
When I arrived about ten minutes late, my date greeted me outside. He held the door as I walked into the coffee shop, abuzz with people. The vibe of Brass Tacks, with its exposed brick and live plants throughout, was eclectic and vibrant — another perfect coffee date option.
After we ordered our drinks, I asked my date how he felt about sitting outside. I know native Houstonians get sicka me – always asking for an outdoor patio, even though the outside thermostat is set on Hell. Luckily, Sky Guy was from the east coast. He kindly obliged my request.
I distinctly remember how as we set out to find a seat, all the tables and chairs were wet from a rainstorm earlier that day. Rather than shifting gears back inside, my date went to find napkins. He made sure to stop me from sitting down before he could wipe the rain droplets off my chair and then signaled me to take my seat once it had been thoroughly dried. Attentive and considerate, I thought to myself.
During our coffee date, Sky Guy shared about his family, his dating history, and how he spends his time. He was an accomplished man, in love with his career, and exceptionally intelligent. He revealed that although in his 50s, he was abstinent until marriage. Apparently, I had found a unicorn – the rare male virgin!
Are you shocked I had gone that far up in age range? Well, so was I. But remember, I’m on a journey. While I know my destination, I’m open to taking new and unfamiliar paths along the way. No telling where they may lead me!
The verdict
As our date progressed, I laughed at Sky Guy’s quirky jokes and shifted in my seat during a few moments of awkward silence. He possessed an authenticity – an innocence almost – that warmed my heart.
Sky guy had done all the things and I enjoyed our conversation. If the number one goal for a coffee date is to determine whether or not you like the person enough to go out a second time, then Sky Guy passed with flying colors. We would see each other again.
So, what’s your prediction about my chances with Sky Guy? Drop a comment below and let me know what you thought about our date. As always, if you’re enjoying this content or want to send me a birthday blessing, feel free to tap the “Buy me a coffee” button or share this post with a friend.
Until Next Time!
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!
I’m liking Sky Guy so far too! He is checking off so many good boxes! But I’m gonna put a pin there with him being a 50 year old virgin! Either he is indeed an incredibly disciplined man who has truly embodied a high regard for sexual intimacy and it’s sacredness OR there is sexual repression and/or trauma there that’s gonna reveal itself sooner or later. I hope he turns out to be a UNICORN indeed! C’mon Sky Guy I’m rooting for you!