The One Thing That Almost Ruined My Perfect First Date with a Wealthy, Mature Man: Part 2

Sugar Baby Chelsea Handler Leave Her Rich Older Man for a Woman

In the mid­dle of din­ner, Bran­don asked me a ques­tion that totally caught me off guard. He looked me straight in the eye and asked, “So Lena, do you ever want to have kids?”

It was the kind of ques­tion that every nosey old lady would ask upon find­ing out my age. I was always anti-kid. I was never going to sad­dle myself with a par­a­sitic human being for 18 (or even more) years of my life. Sure, kids were cute, but only when they were some­one else’s prob­lem, and def­i­nitely before they reached their attitude-filled teenage years. I wasn’t an only child by any means; I had three younger sib­lings. And it was through the respon­si­bil­ity that my mom gave to me with my youngest sis­ter that I knew exactly what I would go through if I were to ever have a child. So when Bran­don, the man who was peer­ing at me with a quizzi­cal look on his face, asked me the dreaded ques­tion­about whether I ever wanted to have kids, I had to won­der: was he look­ing for a sparkly new baby machine or some­one who was in their right mind to not want any?

At this point in my life, I can hon­estly say no. I’m not really a kid per­son,” I said. And with that being said, it seemed that Bran­don was a lit­tle relieved. So he wasn’t look­ing for any more kids—thank god! He already did have a son, and I’m sure that was all he really wanted. To my sur­prise, Bran­don then men­tioned that he had a younger daugh­ter who was still in ele­men­tary school. I already had to think about the fact that he had a son, and now he also had a younger daugh­ter still need­ing his devoted atten­tion. But Bran­don put me at ease when he revealed that he only saw her two days out of the week. I wasn’t as per­turbed by the idea of being with a man with two kids, but then again, I did not see a rea­son for our fling to become any­thing else.

The rest of the din­ner con­sisted of ques­tions and answers from both Bran­don and I. We were find­ing things out about one another. Bran­don wasn’t as secre­tive and mys­te­ri­ous as I thought he would be. He was an upper-level man­ager and so his choice to keep his life pri­vate was under­stand­able, but I didn’t need to pry answers out of him. Then it got me think­ing, I was really here sit­ting down with the man­ager of a high-end office. Bran­don wasn’t nec­es­sar­ily my direct man­ager, but he was a man­ager for the same com­pany that owned the office I was a part-time sec­re­tary for. He was, in other terms, my indi­rect man­ager and the office romance scan­dal was some­thing I wanted to keep brush­ing off. What would the rumors and gos­sip say about me? “There goes the skank try­ing to climb the cor­po­rate lad­der, one middle-aged man at a time.”

I shook my head, try­ing not to dwell on it too much. For all I knew, Bran­don was just look­ing for a good time deal and that was that. But see­ing how he lis­tened to every sin­gle thing about me and how he looked at me like I was the only woman in the room, I had my doubts.

The rest of the night went per­fectly. Once we were done with our din­ner and dessert, we made our way over to one of the fire pits near the duck pond. The fire only slightly warmed up my bare arms. Bran­don noticed and offered to put his arms around me. I was instantly nice and cozy and that was when Bran­don leaned in and asked if he could kiss me. It was, with­out a doubt, the per­fect first date with an older man.

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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.