This Is What Happens After You Give Your Hot Older Boss Your Cell Phone Number: Part 2

Age-Gap Celebrity Couple Peter Berg and Whitney Cummings

I’m kid­ding, Lena! I don’t want to scare you away. I’m just try­ing to be funny,” said Bran­don. I gave a small chuckle as Bran­don con­tin­ued to reas­sure me that he wasn’t some horn­dog. But I found it funny that he felt embarrassed.

As we laughed and changed the sub­ject, we found out that we actu­ally had a lot in com­mon, like our musi­cal tastes. Some­times it was just like speak­ing to some­one my own age. In fact, our big age dif­fer­ence was never appar­ent in our con­ver­sa­tions unless he referred back to his child­hood mem­o­ries or I regaled him with some of my own. One thing that did stand out to me how­ever was the nature of our con­ver­sa­tions. Not once did my ex Jared, who was my own age, ever seem inter­ested in what I had to say—Brandon was the com­plete opposite!

Bran­don was impressed with my deter­mi­na­tion to fin­ish school while work­ing part-time to sup­port myself. I was a breath of fresh air for him, a com­plete con­trast to the other women he had dated.

Every sin­gle morn­ing from there on in I woke up to a text mes­sage that read, “Good morn­ing, beau­ti­ful,” fol­lowed by a smi­ley face. Sure, it was cheesy, but Bran­don was any­thing but dis­hon­est and his opin­ion of me being beau­ti­ful was noth­ing but the truth for him.

It took Bran­don two whole weeks of talk­ing over the phone and text mes­sages to work up the courage to ask me out on our first date. And that’s when real­ity set in. Was I pre­pared to go out in pub­lic with a man who was old enough to be my father? Was I ready to deal with the stares from strangers? Would I be judged? I was about to find out…

The day of our first date came and I was all nerves. I was bom­barded with worries—were we going to be looked at? Was our age dif­fer­ence appar­ent? It was hard to tell, because I had con­fused Bran­don for being in his 30s when I first met him six months ear­lier. Being 20 myself, I was hop­ing I looked sev­eral years older than I really was. It wasn’t as if I didn’t know this was going to be a prob­lem with me; I knew our age dif­fer­ence would be an obsta­cle, but I guess I just never thought that we would really be going out on a date one day.

Through­out my infat­u­a­tion with Bran­don, I ques­tioned whether or not my crush on this older man was just a pro­jected sub­con­scious daddy issue, as peo­ple like to assume when they see a younger woman with an older man—a poor naïve, easily-influenced girl work­ing through some deep-seated father issues.

As it so hap­pens, I was brought up with a father who spoiled me rot­ten and always told me to fol­low my dreams. I was also given another father-figure with my step­dad, who always knew when to bring my head back down to earth when it reached the clouds. In no way what­so­ever had I ever been deprived of fatherly love. So what I really wasn’t look­ing for­ward to was the talk, “Lena must have a lot of daddy issues.” And till this day, it is still some­thing that I deal with. But luck­ily for me, I put any neg­a­tive thoughts away that night the minute Bran­don opened his car door for me.

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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.