Free shipping on orders over $100

Dating an Older man? Watch out for This

I was having a major soul-searching moment. It was sparked by another failed dating attempt. So, I decided to change my life around -yet again. I canceled all plans and forced myself to sit in and read self- help books. I also called my spiritual friend Carmelita for help. She’s the most poised and calm human being on earth. I’ve never seen her get angry or stress about anything- not even a man. She’s always been goals. I was willing to do whatever she advised to getting me out this funk. But, little did I know, her advice would push me into more dating- except this time with older men. I’m not upset about this push; dating an older man was great in every area. Well, every area except one. 

Carmelita invited me to a church that Friday night for an adult-mingling event. Ehh… why not? From the moment I walked in, I finally realized why Carmelita stays so happy. This event was flooded with nice-looking older men. I whispered to Carmelita, “Are you sure this isn’t a salt and pepper stud convention?” She chuckled and said, “Just enjoy yourself.” My soul-searching-single journey went out the window that quick ya’ll (shrugs). It was time to get my Christian-mingle on. 

There was one older gentleman named Chester that found me at the beginning of the event and consumed all of my time there. I know, his name is sketch AF. But, his charisma was magical. I didn’t want our conversation to end. I’m not bold enough to ask for a nightcap after a church event. So, I asked to keep in touch. He requested my email (side note: older men love to send emails.) About two weeks later, I finallyreceived an email from him. It was nothing like I had imagined either. He sent me a book recommendation and invited me to dinner the following night. Wow, his book recommendation was on point. And, I didn’t have to take initiative and make plans. The restaurant he invited me to, was nothing I nor any guy I’ve ever dated could afford, too. Dating an older man was off to a great start. 

At dinner, the restaurant was open only for us. Baller, right? It turned out Chester was an investor of this restaurant. I learned just about everything I needed to know about him that night. He was an open book and willing to tell me everything – as long as I did the same. I valued the up-front and honest terms set by him. Usually, that’s something I have to beg for. I could sense that no childish games would be played… but, there was an unexpected game lurking. 

Chester was 54-years old, which was 28 years older than me at the time. His occupation was a real estate agent and investor in several businesses. Chester was a gym fanatic, father of 11-year-old twin girls and a chef in his little spare time. He was African- American with rich mocha skin that was wrinkle-free, 6 feet tall, and a very fit body. And, even though he was a businessman, suits were not his forte. He loved to wear Nike gear accessorized with a nice Rolex. 

On the very first date, I asked about his love life. I was certain he’d been married before. Surprisingly, Chester was never married. The mother of his children had been his fiancé at one point in time. However, he said while engaged she decided she no longer believed in marriage and their relationship ended unanimously. On the first date, I stopped prying in his past love life for one reason. I didn’t want him prying too much into mine. I wanted him to stick around. I couldn’t tell him I just had to key a car and lost my job due to a stupid ex a few weeks ago. 

The dates happened every weekend and soon multiplied to every other evening. I told my other friends about my dating of this older man around the third month. Of course, the group chat flooded with questions about sex. The rumor that older men are better in bed is absolutely true. Chester explored my body and satisfied areas that I never knew I had feeling in. He didn’t get tired either, I tapped out way before old man did. This sex was so good, I couldn’t see myself having sex with anyone else ever again. I wanted to be his lady.

Dating him was easy, fun and motivating. I yearned for this in my life. He always stressed a go-with-the-flow mentality. Therefore, he despised titles. I was too scared to ask to officially be his girlfriend. I didn’t want to ruin the “flow.” Besides, I did all of the girlfriend activities. I met his children, co-workers, and siblings several times. It had been six months and I was getting anxious for affirmation that we were locked in. 

By month six, Chester and I had not argued once. I can’t recall a time I ever had to raise my voice at him. Until the day I went to his daughters’ recital. It would be my first time meeting his mother and his daughters’ mother. Both of these women were very polite and respectful. I had no issue with them. Although, I was shocked to see that the twins had a stepdad. I was never informed of that detail. I thought their mom didn’t believe in marriage. After the recital ended, Chester introduced me to his daughters’ mother, stepdad, and his mother as his friend. My emotions went wild!  

What made it even worse, was as he said friend, I caught a look of disgust from the twin’s mother. It was as if she was saying, “He still hasn’t changed.” That’s when the first argument happened. I had to confront him about our status. How could I still be just a friend after all of this? We’ve kissed in front of your kids and I’m even listed as a family member on your gym membership. His response to my emotional uproar was: “I don’t do relationships and if that’s what you want maybe you have the wrong understanding about this arrangement.” Arrangement?Now I felt like an escort. 

It became clear. His ex-fiancé did believe in marriage – he was the one that didn’t. He didn’t have girlfriends because he never wanted to commit. I was beginning to fall in love with Chester. There was no way I could continue to be happy knowing I would never receive a commitment. This was a hard decision (I couldn’t fathom losing his sex) but, the cut off was real. I went straight Carrie Bradshaw to Biggs; blocked his calls, texts and even emails.

Here’s my theory about older men from my experience and experience from my friends. Older men are great for their maturity and stability – but they never want to commit to younger women. So, it ends up becoming this weird companionship that the younger girl will eventually get tired of. The older man doesn’t mind it though, he will move right along to the next young girl and test her patience as well. Do you agree? Have you ever had an older many ready to commit?   

Posted in

T. Rogers

T. Rogers is a reader by day and writer by night. With over 7 years of content writing, she continues to prevail in her world of sour patch kids, expensive shoes and awkward moments that spark her courage to tell the greatest stories never told.