What to Expect From Your Much Older Boss After He Flirts with You at the Company Christmas Party

After the long awaited hol­i­day party, my rela­tion­ship with my older crush seemed to change. Much to my heart’s con­tent, Bran­don had made it a point to look for me that night at the com­pany party. And with that, my best friend Melinda made me real­ize that I was really play­ing with fire. My flirt­ing with the man­ager of a respectable office was becom­ing more seri­ous. My emo­tions were all mixed up. I was start­ing to get scared that I didn’t know what I was doing try­ing to play around with a man who was 26 years my senior. And if he really wanted a com­mit­ted rela­tion­ship, was I really up for it?

This was becom­ing more than just an exchange between a wolfish man­ager and a flirty sec­re­tary. It was becom­ing the poten­tial rela­tion­ship between a sin­gle, older man and a much younger woman who believed she could take it all on. I was start­ing to become a lit­tle hes­i­tant about the whole sit­u­a­tion and doubts started to set in. It wasn’t as if Bran­don had asked me out, he just was more forth­com­ing with his attrac­tion for me than I was read­ily admit­ting. At that moment, I had to make a decision—would I con­tinue my mis­sion to seduce this man, or would I tone it down and set­tle with look­ing for some­one my age?

Weeks passed and I rang in the New Year with Melinda and our fam­i­lies. That was when my sin­gle­ness seemed to glare at me. Sure, Melinda was sin­gle just as I was, but I wanted to kiss that spe­cial some­one at the end of the count­down and Brandon’s face would pop up any time my thoughts went in that direction.

I expected things to be a lit­tle dif­fer­ent between myself and Bran­don, and it was, but not in the way I thought. Once again, I was get­ting the cold shoul­der by Brandon—the same thing had hap­pened after I admit­ted to him that I read erotic fiction.This man could not have been any more con­fus­ing. I was sit­ting at my desk doing my typ­i­cal paper­work and Bran­don walked in.“Good morn­ing, Lena,” Bran­don said as he looked over in my direc­tion, as if he was hes­i­tat­ing to say some­thing else.

Good morn­ing!” I replied in a cheery tone. I was happy to see him and ready for what else he had to say. After the hol­i­day party, I hadn’t seen Bran­don for almost three weeks and that was a pretty long time. But instead of pro­long­ing our con­ver­sa­tion, he gave me a quick nod and a polite smile.

Good. Is Calvin in?” And with that, he went on his busi­ness to see my manager.

I didn’t know how to take it. Was he seri­ously going to act like there was noth­ing between us? Pissed off and a lit­tle humil­i­ated, I sent an angry text to Melinda: “I’m done. I need to get over this guy. Who am I kid­ding? He’s older than my dad! He can’t even act like he knows me and pre­tends to not know that there’s some­thing between us. He’s just a typ­i­cal flirt. I don’t need that!”

Lit­tle did I know what was really going on with Bran­don and that he actu­ally had a plan of his own.

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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.