One afternoon as I was having a quiet lunch, I was approached by a handsome thirtysomething year old who asked if he could sit with me.
When he sat, we ended up talking about a handful of different things and happened to dive into the topic of relationships. As we spoke, he shared his desire to have a wife and kids. As I listened, he shared that although he wanted a family of his own and had dabbled with dating and juggling different women in the “talking stage”, he expressed that women have always been a vice for him. “I date a lot of pretty girls, but I don’t feel like there’s been anything more than that with them,” he explained.
“Like are they dense or something?” I jokingly asked.
“They’re not blatantly stupid,” he replied. “They’re just pretty, and I’m looking for more.”
Interesting, I thought.
He talked to me about his past and what he was seeking in an ideal partner (someone who’s attractive and smart on the inside and out), and went on to share his unicorn-like status as a Black thirtysomething male: he’s single, has no kids, a great credit score, and feels that he’s finally settling into a more stable career – and mentioned other goals he has in mind for his future.
He even talked about a brief college romance with someone who sounded like she could have been the one who got away: a successful attorney he couldn’t appreciate at the time. Back then, he was taken with the attention he’d been receiving from other young women on campus, so the rising attorney passed him by.
“I fear that I won’t meet a woman who can grow with me,” he shared. “If I choose a career and then want to do something else, and I’m in a relationship, I have someone else I have to think about if I want to make changes.”
As he continued, he shared stories with me about a handful of different women he’d been involved with and how some of them seemed to really hate him. When I asked him why this might be, he explained that some of these women were upset about misplaced expectations, being friend zoned, and not feeling that he was truly committed to them. He went on to share that he’s nice to every woman he meets and that his kindness and “just chillin” with these women had left some of them thinking he was interested in them.
“Do you think maybe your kindness comes off a little flirty?” I asked.
“Also, you might keep missing the right woman who may exist among the many you’re trying to keep up with. My grandma once told my uncle (before he settled down) that he would never truly “see” who his wife was because he was too busy entertaining every woman who came his way.”
He paused and got quiet.
As he pondered, I went on. “Most, not all, but most, thirtysomething year old women aren’t out here trying to just chill or be another girlfriend. They’re looking to settle down.”
He nodded as I spoke.
“It sounds like you’ve been in a handful of situationships with these women, and you need to stop doing that. Do the work on yourself and heal.”
“Also, you should probably consider seeking a male mentor and linking up with someone who’s been married for at least 10 years or so who could offer some wise counsel. I think you need to be with someone who challenges you intellectually too,” I added.
Then he laughed.
As we talked a little more, we walked together, and I just listened. I wondered if he’d ever talked to any of the different girls he’d casually been seeing about everything he was sharing with me. He went on to share some more personal things that gave me a little insight about what could be going on with other men in their thirties trying to date and perhaps wanting to settle down too. I thought about their silent fears, private insecurities, and their massive dreams as well.
When we continued walking and approached a door, he got ahead of me to open it and said, “See, chivalry isn’t dead.”
I smiled and we parted ways.
I enjoyed our conversation. I even felt lucky because not many women get the chance to sit down with a guy who opens up like he did. Before writing this, I reconnected with him to ask if I could blog about our talk because I believe a lot of women could benefit from a male perspective. He said yes, and here we are.
I wonder how dating would shift if more guys felt safe enough to sit down with a woman who was open to listening to them and courageous enough to be honest and open about their challenges, goals, fears, and more.