The Worst Time in Your May-December Relationship to Bring Up the Topic of Marriage: Part 2

For the most part, Bran­don and my May-December rela­tion­ship con­sisted of both of us flirt­ing and won­der­ing about each other for six months before either of us made a move. It took all the courage I could muster to be the one to make the first move and it didn’t take long for Bran­don to jump on board and ask me out on a date. After a beau­ti­ful din­ner and a heavy make­out ses­sion, Bran­don openly expressed that he could see him­self mar­ry­ing me one day.

Not hear­ing any­thing but the word “marry,” I got scared and started to reeval­u­ate what exactly I was look­ing for from Bran­don. But when I opened up about my con­cerns of our May-December rela­tion­ship going a lit­tle too fast, Bran­don jumped ship and sug­gested that we just be friends, which is when I real­ized that what I really wanted was for Bran­don to be my boyfriend.

After going through a whole day with­out hear­ing a peep from him, I decided that this wasn’t the kind of guy that I wanted to miss out on. I decided to send a text mes­sage to Bran­don explain­ing what exactly I was feel­ing and that I did not want to just be friends, but that I wanted us to go slow. To my relief, Bran­don expressed the same idea and even con­fessed that he felt bad the entire day because he missed hear­ing from me. It was then that we both came to the con­clu­sion that we clearly felt the same way about one another and that any­thing after that was, in Brandon’s words, “God’s will.”

Now that we had our feel­ings for one another out on the table, Bran­don and I con­tin­ued what we had. It wasn’t until the next week that we real­ized Valentine’s Day landed exactly 10 days after our first date, which cre­ated yet one more obstacle—no one at work knew about our office romance. The stress of dat­ing one of the man­agers sud­denly started to rear its ugly head again and I had to think, how was I going to tell peo­ple? Or rather, who needed to know and who didn’t?

Out of respect and pro­fes­sion­al­ism, I imme­di­ately told my direct man­ager, Calvin, about what hap­pened and asked what he thought of it, or more impor­tantly, if he allowed it. To my sur­prise, Calvin was excited that his long­time co-manager had found some­one. Though I was a lit­tle young, he knew I was mature for my age and as long as my May-December rela­tion­ship did not inter­fere with my work ethic, then he was all for it. The rest of my office was happy to see me happy and even had an inkling about the attrac­tion between Bran­don and I.

How­ever, Brandon’s office wasn’t so thrilled, espe­cially Becky, one of Brandon’s employ­ees whom I had sus­pected had a thing for him. Luck­ily for the both of us, the com­pany was used to employ­ees dat­ing one another and there was not much they could do. So we were free to do what we wanted as long as home and work were sep­a­rated. Things were finally start­ing to work in our favor.

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About Lena

I’d always dreamed of the perfect fairytale prince in storybooks—ready with money and status to come save me from my chaotic, average life and treat me like his princess. Add a 26-year age difference and I found the closest thing to it. Not everything comes as easy as we expect it to, but that’s what makes it all the more fun. At 18 years old, I experienced that “Mr. Right Now” love with a guy my age named Jared. Two years later, I met Brandon, my older man. Jared was the typical playboy who romanced my naïve younger self and made me fall hard for him. That relationship caused me to view love in an entirely different way than I previously had, and I’m actually glad it did. By the time I met Brandon, I had become wiser and more prepared for the reality of relationships. Even though at 20 years old I didn’t show the tell-tale signs of a smart, mature woman, that was exactly what I had become. I started as a part-time secretary for a highly respectable office, while juggling a full-time load of college courses at the local university. It was my first official job where I had to wear heels, pencil skirts, and an occasional suit. I was no longer the high-school girl that found “true love” after graduation and had her heart broken immediately after. The new woman I was now was confident and smart, and when I saw Brandon walk through the lobby door, I knew he’d be a challenge, one I was ready to accept. Now at 22, and Brandon at 48, we’ve managed to keep a two -year relationship feeling like the very first day we met—all the excitement and butterflies are still very much present.