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 share the challenges of dating at forty. Enjoy!
Now that my Nawlins rendezvous is over, let’s head back to Houston! It’s time to fill y’all in on the rest of my “roller coaster summer.” New Orleans was just the start – it’s been an eventful season, to say the least. There were lots of dates, lots of fun, and unfortunately – lots of downs. I’m inclined to say there were more downs than anything else, but in actuality, my romantic life was nothing short of a roller coaster ride. One minute, I was hopeful and excited; the next, disappointed and sad.
If I’m honest, I might have preferred no dating life over the roller coaster of a summer I had. In a matter of two months, I experienced limerence, ghosting, and even zombie-ing – you know, when men disappear and then reappear back from the dead. Honestly, I would have much preferred if they had all just left me to my peace and never spoken to me at all.
In The Bible, King Solomon says, “It’s better to sleep on the corner of a roof than to live with a quarrelsome wife.” BARZ, Solomon! Some people and their foolishness will make you wish for solitude.
Cougar Vibes
Without a doubt, my roller-coaster summer has impacted my outlook on dating. And then I turned forty, which has imposed its own mental gymnastics to work through.
Now, don’t get me wrong. I’m not lamenting my twenties. I don’t wish to go back to the days of ramen noodles and nonexistent boundaries. I love forty-year-old me! I’m more clear about who I am and more compassionate with my humanity. I know what I want and trust myself so much more! I’m stronger, more resilient, and self-sufficient. But there’s also another side to forty . . .
It may seem ridiculous, but as a never-married single woman who desires marriage, forty feels acutely different than thirty-nine. There’s an awareness that I’m middle-aged – which means I’m older than nearly half the planet. Yet, I don’t see a middle-aged woman when I look in the mirror. And, even stranger, most of the men I’m meeting are now younger than me. Apparently, I’ve entered cougar territory — and I feel a way about it. 😒
The youngest of them all was a beautiful Afro-Latino man. We passed one another at The Galleria Mall, met eyes, and he later approached me as I wandered around Zara. After a few days of texting, I sensed he was a youngin’ and inquired about his age. That baby said twenty-six years old!
Abeg?
Now, I like ’em younger – but not that young.
I promptly released him back into the dating pool.
The Same Ole’ Forty
Aging can be a funny thing for a woman. In many ways, she becomes the best version of herself. She’s likely wiser, wealthier, and more settled into her womanhood. She knows who she is more than she ever has. But as she’s evolving and growing, the world whispers a different message to her. It quietly shouts, “Youth reigns supreme!” And it’s always loudest when said woman desires marriage and family.
Tick-tock, tick-tock goes the biological clock. Although I’ve never been consumed with the idea of motherhood, I still would like the option. As I date, I become increasingly aware that my window is closing.
Time waits for no one. While I don’t feel I’ve aged drastically from my twenties, I still have to agree with my guy Lyfe Jennings. “Thirty is not the new twenty. It’s the same ole thirty” — and forty’s the same ole forty . . .
This is NOT Never Never Land.
And my conversations with men are only adding to the issue.
Jazz Fest Guy
At the end of the summer, I met a man at Miller Outdoor Theater during a jazz festival. He was a bright-skinned Black man, slim with curly hair–and a decent, though slightly pushed-back hairline. I enjoyed his witty banter and how he approached me, offering bug spray because I was heading to the park at dusk but wearing a sundress. During our short exchange walking into the park, I learned he appreciated the arts and was a beginner salsa dancer–all good things!
A few days into texting, I asked about his dating goals. He told me that at thirty-seven years of age, he was looking to “go with the flow.” That was the first yellow flag. When I playfully told him I was looking for someone to “take me out the game,” he inquired about my age. I told him “forty”. Jazz Fest Guy followed up, asking if I wanted kids, and added, “Sorry to be blunt, but it’s because of the age.” His words stung — not the “do you want kids” part, but the unnecessary follow-up commentary.
Do we really need to qualify asking a woman if she wants kids while on a date? 🙄 The knee-gro knew he was about to say something insensitive but did it anyway. One thing they will never lack is audacity. 😒
The next day, Jazz Fest Guy told me he didn’t think he would be the one to take me out the game, but was open to having fun if I was.
Now, before we judge him for being unserious, let’s remember not every man is meant to be a husband. Some are just meant to provide laughter, fun, or simply an excuse to dress up. Had Jazz Fest Guy taken more care in how he communicated his thoughts, I may have been open to exploring a new friendship, but the “blunt” nature of his delivery had rubbed me the wrong way. I would not be having fun with him.
It could be the men are becoming younger. It could also be their questions are becoming bolder. Or perhaps it’s simply the weight of our society and its obsession with youth. Whatever the reason, turning forty seems to have thrown a bit of a loop into my journey to one hundred dates. 🥴
Dead End Dating
So, there was Jazz Fest Guy and then the gorgeous Afro-Colombian baby. I shared a date with neither. But a few other men, all younger than me, came into orbit that summer as I navigated turning forty. Here’s the story of Date #33.
Mr. Confidence
We will call date #33 “Mr. Confidence” because he led with confidence – although I’m not quite sure how confident he actually was. We matched on Hinge just before my trip to New Orleans. I liked that he had a very grown-up hobby, golf, listed on his profile. He was a man of faith and had been photographed addressing a crowd. Was he a preacher? 👀 Lawd, let’s hope not. 🙏🏾 As Auntie Chelle (Obama) has shared, the seat of the First Lady is no easy throne to fill. Whether she’s First Lady of the United States or First Lady of Brookside Bibleway Baptist Church in Birmingham, Alabama, a woman must be mentally tough and prayed up to fulfill such a role.
Mr. Confidence’s face was familiar. As I chatted with him, I sat back, trying to recall where I’d seen him before. And then it came to me. We’d matched on Bumble earlier in the year, but somehow, one or both of us had dropped the ball.
This time, I would make sure that didn’t happen. Shortly after transitioning off the app, I proposed a meetup.
“Are you about that action, (Mr. Confidence) 👀?”
“I’m about…action. Period, Kaity:”
“So, how about this? I typically don’t text for long before I like to do a quick meetup. How do you feel about a quick coffee date tomorrow or Monday to see how we vibe in person?”
Mr. Confidence was receptive to my request. We scheduled a time to meet up at Brass Tacks coffee shop.
When I arrived at the coffee shop, Mr. Confidence greeted me. He was a sawed-off little man of about five feet, six inches, wearing glasses and a pink polo shirt. Now, don’t get me wrong — he was handsome. His head was full of soft, three-C coils, trimmed into a Brooklyn cut with a tapered (and full) hairline. His skin was a healthy golden brown.
In the light of day, Mr. Confidence was easy on the eyes. Height has never been a deal breaker for me— I’d just make sure I only purchased kitten heels from that moment forward. 🙃
Mr. Confidence and I sat outside the coffee shop under a tree for about two hours, discussing everything under the sun. He loved his work and served faithfully in his church. He humored the psychology nerd in me as we explored human behavior and relationships, theories, and current events.
Dating Superpowers
Along my journey to 100 dates, I’ve discovered an interesting detail about myself. I have a dating superpower! Everyone does, really. It’s just a matter of staying in the game long enough to recognize it. I’m going to call my superpower “curious connection.”
I’m a naturally curious person. Whether it’s about people or facts, I love learning. I suppose it’s what makes me a good therapist. Curiosity prompts me to ask questions that convey interest in my subject. And most people have an all-time favorite topic: themselves! Having a genuine curiosity about a man and his way of thinking will not only eliminate the possibility of boredom, but it can be a turn-on for a smart man. Sprinkle in a bit of vulnerability in sharing about yourself and viola! You’ve got a connection!
Every woman should learn her dating superpower simply because it helps build dating confidence. If you don’t know yours, continue to date and look for your strengths and patterns. What compliments do you frequently receive beyond your appearance? What dating skill are you confident in?
I’ve learned through going on a ton of first dates that I can connect with nearly anyone on a first date. Very few (if any) men have ghosted me based on a first date—maybe shortly after, but never after the first! 🙃
Mr. Confidence was no different. We talked and talked that afternoon. I enjoyed the connection for the most part. Sure, he was a bit pretentious and sometimes sounded as if he was interviewing for a job rather than on a date. He ran down his resume and professional achievements. Though he demonstrated an air of confidence, there were pockets of conversation during which Mr. Confidence felt disingenuous – hollow even.
As we chatted, he gloated that he would never bring a woman he was dating to his church because too many people would be in his business. I mean—I guess. So much for praising the Lord together. 😑 He seemed to be preoccupied with other people’s opinions.
I wonder how he would feel about this blog. 🤔
The Flags are Flaggin’
None of these factors were enough for me to drop Mr. Confidence at the time. I would file them away as I continued to feel out his character. However, he eventually shared a story that would ultimately dig his grave. As I think about it, after sharing that story, Mr. Confidence never really stood a chance. Only it would take time for my conscious brain to catch up with my subconscious feelings.
As he shared his growth in the past year, my date mentioned how he’s learned he needs to be more compassionate. According to him, he reserves patience for students and young people, But in most matters, adults should know better.
Mr. Confidence went on to share he had recently lost an aunt due to health complications associated with being overweight. That man looked me dead in my face and told me that, unlike the rest of his family, he didn’t feel very badly about her death because – in his words – she “did it to herself.”
Well, dayum! Them red flags is flaggin’, ain’t they!
If Mr. Confidence could take that attitude with his own flesh and blood, there’s no telling how he would handle me. I’m as sensitive as they come and require a compassionate man. A man who doesn’t have access to empathy would be a horrible match.
Despite my secret judgment, we finished our date pleasantly. Mr. Confidence walked me to my car and hugged me goodbye. He mentioned seeing me again. At the moment, I was open to the possibility and hadn’t fully processed my feelings about him.
However, in the following days, as I sat with myself, my interest in Mr. Confidence began to wane. In addition to his revelation about his aunt, something about his vibe just rubbed me the wrong way.
He would drop hints about doing big things in his personal life but refused to answer my follow-up questions. Why drop hints if you don’t want to share? That’s weird. Instead, Mr. Confidence opted for responses that teetered the lines of flirtation and arrogance.
“I’m like cognac, Kaity. You gotta sip me slow.”
I mean— I guess.
As the week drew on, my response times to Mr. Confidence’s messages grew longer and longer. He inquired about a next date, and I remained open – though admittedly skeptical. One more date would either cement my feelings or turn things around.
Ghosts and Goblins
However, Mr. Confidence never came through with those plans.
One day, while passing time texting about how I’d recently purchased a ladder for my home, Mr. Confidence asked, “What on earth are you building?”
“Lol. Not building anything,” I replied. “I bought a townhouse this year. There’s texture on all my ceilings that I want to remove.”
Perhaps he was turned off by the idea of my being covered in drywall dust. Or maybe Mr. Confidence could feel my energy shift as I took longer to reply to him. Maybe he’d learned about my journey to 100 Dates. 🤔
Whatever it was, I never heard from him again –and I was perfectly fine with it. I’ve lived long enough to know not to force a square peg into a round hole.
That’s one ghost for the summer of 2024. Stick around to see how many more there will be!
Back to the dating train we go!! 🚂
So, was it me? Am I the problem because I should know better? What do you think about dating younger men? Fun or foolish? Let’s hear it in the comments!
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 don’t see anything wrong with dating younger, in fact, I encourage it! Most of the men I have dated have been younger, in fact. I actually think that the more you get into your 40s, especially if you live a certain lifestyle, you will attract more younger men and rightfully so! However, I assume that most men who are actually looking to “settle down” are going to be older than 35, so I no longer date men who are younger than 37. This keeps me within a 10 year window. I think you need a larger sample size of experiences before you write off younger men entirely. Think about judging men moreso on where they are in life (professionally, emotionally, mentally) than their age.
Give younger men a try because maturity and EQ aren’t based on age. Plus they keep us cougars young ✨️
I also enjoy how you accept you are a sensitive woman and avoid men who can’t nuture your style.