100 Dates in Houston: Roller Coaster Dating

Aug 22, 2023 | Blog | 0 comments

My love life lately has felt like something straight off of an episode of The Bachelorette — complete with all of the twists, turns, and emotional meltdowns. After my sudden crash and burn with the Beard, date #6 almost didn’t happen. I felt sad, heavy, confused, and discouraged. It felt pointless to go out with another man, knowing that a date could fall flat so quickly – and seemingly without notice. Why bother getting my hopes up? Suddenly, dating in “volume” had begun to feel like a chore – and at that moment, I wanted no part of any of it.  

Clearly, I’d overestimated my ability to navigate rotational dating when I scheduled The Beard on Saturday night, followed by time with Mr. Hairline on Sunday night. I thought, Why don’t the dating coaches tell you to allow time between dates to bounce back from disappointments? Maybe it’s me? Maybe I’m the problem. I shouldn’t have been feeling so much so soon. Maybe I’m doing this all wrong. I’ve put in all this work and I’m still messing up. 

Old habits die hard

My mind stormed with negative thoughts. In a matter of hours, old narratives and negative core beliefs I’ve spent years correcting rose to the surface. Suddenly, I was back to being that girl that was ridiculously hard on herself and looked inward for everything wrong in life.  

That’s the thing about setbacks. When we encounter roadblocks to our goals, we become vulnerable. Pain will trigger our old habits and narratives. If we aren’t careful, it’s really easy to give up during these moments and that’s exactly what I wanted to do.

If I chose not to throw in the towel, I would have less than 24 hours to get my head together, show up, and be present with another man. Listen, I won’t be doing that again. From now on, I’ll give myself at least two to three business days between dates just in case a reset is needed! 😮‍💨

Looking back, amid my struggle, I gave The Beard way too much power over my outlook on my love life. Caught up in the fire of chemistry, I had forgotten that my primary purpose that evening was to assess compatibility and alignment — The Beard and I simply weren’t aligned. Instead, the lover in me was expecting to have a riveting time and perhaps ignite a whirlwind romance that would lead to settling down with the love of my life. 🤷🏾‍♀️

Don’t blame me; blame Hollywood and hormones. 

Hey, what can I say? At the end of the day, I’m still a woman. I’ve learned the value of self-compassion and permit myself to get caught up every once in a while. It’s par for the course of being human. It also makes life spicy and fun. If we can’t expect to have a little fun while dating, what’s the point? 🤷🏾‍♀️  

Having emotions vs being emotional

Despite the fact that my feelings told me to retreat and maybe even give up, I had committed to spending time with Hairline the week before. Because I’m learning not to react impulsively to my emotions, I resolved to follow through on that commitment. It was the difference between having emotions and being emotional.  

Working with Joyice (my coach and friend from The Curious Case of Mr. Beard) has really helped me manage my big emotions. She calls the concept of waiting to respond to your emotions Feel and Chill.  According to her, most of us do one of two things when we feel big emotions: react or suppress.

First, we may react and do whatever the emotion is telling us to do at the moment. For example, we block a man or send a long, angry text because he’s triggered frustration by taking too long to respond to a phone call. If we’re not reacting, we’re suppressing the feeling and acting as if it doesn’t exist. When the man doesn’t respond to a call, we don’t react and send an angry text; however, we also don’t address the problem at all. We feel frustrated, yet do nothing. We may even try to talk ourselves out of the emotion. 

Neither reactivity nor suppression is healthy. Emotions need to be felt because they give us valuable information. However, due to trauma, misunderstanding, and people people-ing, emotions can also be off-base and fleeting. They need to be properly understood before determining the best course of action to take.

With Feel and Chill in mind, as well as being a woman who values keeping my word, I decided I would push past my difficult feelings for the day and show up for my plans with Hairline. If apathy and disappointment continued for some time, I might take a break from dating for a bit. But for the time being, I will remain in the game. 

Redemption

On the day of our date, Hairline texted me around noon to inquire about an itinerary since we had not firmed up what we would be doing.  Earlier in the week, we had discussed watersports on the lake near my place; however, the rain had other plans. Weighed down by the disappointment of the previous date, I didn’t have much to give in the way of planning. So I put the ball in Hairline’s court and asked if he would prefer to do a rain check or find an indoor activity. He opted to do some research and booked reservations at Hearsay on The Waterway in the Woodlands. Perfect! My drive would only be five minutes away from my house.  

Hairline arrived early this time, and despite my five-minute drive, I was about ten minutes late 🤦🏾‍♀️. He graciously greeted me and we made our way to the balcony seating overlooking the waterway. Always a sucker for outdoor seating and pretty backdrops, I was pleased. 

Our conversation that night was easy. We reminisced on our experiences as former Gamecocks. Hairline and I had both attended the University of South Carolina but didn’t frequent the same circles and never had a formal introduction. I found it amusing that he had been pretty good friends with my college sweetheart and ex-boyfriend (three times removed). The man is now married and that was ages ago, so we figured it didn’t matter much.

Mr. Hairline told me stories about dorm room encounters with the palm-sized water bugs often spotted on campus at USC. He shared about the sheer terror of witnessing a snake – likely just the little garter kind – slither through his air conditioner and into his room one night. *New fear unlocked*. I belted with laughter. It felt nice to enjoy an easy conversation.

Of course, the lover-girl in me came out to play for a bit and decided to ask Hairline about sex. Perhaps he was celibate – or maybe he was a sex addict! I had no idea and wanted to create an opportunity to learn about how he navigates sexuality. I also wanted to have a little fun!  

As a woman, there’s an art to discussing sexuality without being vulgar or, as my grandma would say, “fast”. There’s no need to be suggestive or crass. It can be downright seductive to discuss sex in a way that is curious and matter-of-fact. It conveys “I’m comfortable in my sexuality, but that doesn’t mean you can have it!”  

That night, I watched Hairline squirm a bit as we explored the topic. It was kinda cute to see a grown man a bit uncomfortable discussing adult topics. I concluded that he was a gentleman that wasn’t driven by sex as a primary concern in dating. Another box checked! ✅✅

We left Hearsay on the Waterway and opted to extend the date with a night-time stroll.  Although I had already taken this stroll with Malcolm X a few weeks before, I welcomed the opportunity to experience the beautiful Woodlands Waterway once again – this time, with Mr. Hairline.

It was a totally different experience the second time around. During our stroll, Hairline told me more about his family, his feelings about children, and even some of his fears about relationships. As he went into more detail, I heard some similarities in our stories and appreciated his vulnerability.  

About halfway through our walk, surrounded by trees wrapped in twinkling white lights, Hairline put his arm around my shoulder. I enjoyed his closeness and responded by resting my arm on his waist. We wandered along the path next to the waterside holding one another, laughing and chatting away.

So there I was – taking in beautiful scenery, next to a beautiful man. Mind you, this was the same me who had wanted to cancel the date – the same me who felt discouraged and confused just a few hours before. Not gonna lie — I get on own my nerves sometimes. This is why I’ve worked to not act impulsively on my feelings. An evening that started feeling like a chore, ended feeling like a pleasure!

That night, Hairline was a gentleman. He was present, engaged, and pleasant to be around. I concluded date #6 feeling refreshed and curious about our potential for the future. Again, this was no Carrie-and-Big-fireworks-at-first-sight romance, but that’s not what I’m looking for during this phase of dating. I was glad that I had kept my plans for that evening and wanted to see this match again.

Feeling sure can take you on a roller coaster!

I hope you stick around on this little roller coaster ride! Be sure you’re subscribed and check back next time to find out what happens on date #7. Feel free to tap the “buy me a coffee” button so I can invest in this project and bring you even better content!

Until Next Time,

Be Blessed!

Kaity

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P.S.  Did you know that I wrote a journal? The Confidence Project Journal was created 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!

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