Skip to main content

I had a secret office affair that ended badly

  • Story Highlights
  • Writer met an older man while interning at a magazine and they later e-mailed
  • After he broke up with his girlfriend, they began an affair
  • She got a job at his magazine and their secret affair got awkward
  • After she told him she loved him, he said he was seriously dating someone else
By Jessica Wakeman
Decrease font Decrease font
Enlarge font Enlarge font

(The Frisky) -- We met when I delivered his mail, a task performed by all the interns. But I liked to think I was different: I was an eager little NYU journalism student, desperate for attention, and I chatted with all the editors as I passed their cubicles.

Falling in love among the cubicles at your place of business can go wrong for all sorts of reasons.

Falling in love among the cubicles at your place of business can go wrong for all sorts of reasons.

Many magazine editors on the top of the masthead are a bit standoffish and see interns, especially ones who want to talk while they're busy, as an annoyance. But the Older Man was actually inquisitive and kind; we'd chitchat a little bit, a welcome reprieve from the other editors who could be cold and snappish.

The Older Man and I kept in touch when I moved on to other internships, mostly, I think, because I wanted to use him as a reference. My life was pretty normal for a 21-year-old: I fell in love with a boy my own age, graduated from college, and moved back in with my parents in Connecticut when I took a reporter position at a newspaper.

Over time, "how's it going?" e-mails gave way to exchanging IM screen names and more regular chatting, usually in a mentorship capacity. He seemed to quite enjoy the tales of a cub reporter! And of course, it thrilled me that this big magazine editor thought I was cool enough to IM with.

I was even more thrilled when Older Guy and his girlfriend wanted to have brunch with me and my boyfriend, and when they showed up together at my 22nd birthday party. He read and helped me craft many of the freelance articles I pitched and wrote during that time.

Then one summer, his long-term girlfriend broke up with him. He was despondent and heartbroken and seemingly needed a friend to lean on. I didn't know what was happening at the time, but that's when the real trouble started for me. The Frisky: Dos and don'ts of an office romance

Honestly, I can't say our attraction to each other was a sexual thing. The Older Man is not particularly good-looking, and I'm a little cute, I guess, but really, our personalities just clicked. We were two sad people who met each other at a vulnerable time in our respective lives.

Older Man had thought he'd marry his ex-girlfriend and have her children; he hadn't expected to be 37 years old and single. (As he put it to me once, he thought most unmarried people at that age were the "leftovers.")

I'd moved back in with my parents to the suburbs after college -- a miserable experience for everyone involved. So hanging out more and more frequently with a man 15 years my senior didn't ring any serious alarm bells. On the contrary, the Older Man became the No. 1 joy in my life during that time. The Frisky: How not to date a coworker

For a few months the Older Man and I hung out platonically. We saw movies, plays and a taping of "The Colbert Report." I went on job interviews all the time (he, of course, was one of my references) and we usually met up at Starbucks for a bit, or for dinner, before I caught my Metro North train back to Connecticut.

But then one night after we dined together after a job interview, it hit me that I had an enormous crush on him. I can still remember exactly where I was standing on a particular New York avenue when I realized this. The Frisky: Dating advice for dudes

Then, after we idled away one Saturday away together, it suddenly felt, to me, like we were dating. Operative words here: "to me." But what was I supposed to think? That day, the Older Man and I saw a play together. We walked across the Brooklyn Bridge for pizza and ice cream. We walked all the way back to his apartment in Manhattan and watched movies.

Sitting on his couch after the movies, we kissed. Kissing led to the bedroom and the bedroom led to sleeping together. If it was a "date," it was a perfect date. I can still remember him telling me, with the utmost earnestness, "You are very, very beautiful, by any measure." I felt absolutely over the moon. The Frisky: Obsessing won't make love arrive faster

Then, the magazine he worked for offered me a job at their Web site -- and I took it. The Older Man had nothing to do with my being offered the job -- I promise you that. He told me he said nothing to convince them to hire me and I believed him. I had been an intern at the mag, remember, and I'd kept in touch with people there, so when there was an opening at this other wing, I hustled into an interview.

To my great delight, I got offered the job, which finally meant I could leave my dinky $21,000-a-year newspaper reporter job and move out of my parents' place and back to New York City.

However, working in the same building just underscored for the Older Man how a relationship with a much younger woman was not sustainable. I'd sleep over at his apartment and we'd fool around and then we'd both be at the office as if we were two strangers.

He'd be in a meeting with the editor-in-chief and I'd be a copy machine monkey -- it was very awkward. And the fact that he didn't acknowledge me at work began to make me feel like crap. It took me longer than him to figure this out, but, little by little, I saw the ways in which our relationship was inappropriate -- not just because of our age difference and the fact that we now worked together, but because he didn't treat me like the lover/girlfriend that I considered myself to be. The Frisky: Avoid becoming that annoying coupled-up person

But you know where this story is headed. And it got worse before it got better, of course.

It ended, abruptly, when I told him on the phone that I was in love with him. Sure, I'd shown for months now that I was in love, but I had never verbalized it before. But he had the worst of all possible responses: He wasn't in love with me, he said, and, in fact, he had gone on a few dates with a woman his own age and was falling in love with her.

That news -- a surprise to me -- punched me in the gut with the worst rejection sadness my life. He did care about me as a friend, he said, and he cared about supporting my career, but that was it. In fact, we had to end all of this, tout suite. The Frisky: 10 Celebs who've dated their bosses

The inside of my head was absolute lunacy for several days, but I had to drag my myself to work in the weeks that followed, easily avoiding him. Sometimes when I was alone at the office, I cried, and wanted to run and find him, but I knew it would be unprofessional.

So I did the only thing I could do. I left for another job within a few months -- thanks to Older Man who was still on my resume (oops!) and charitably provided me an excellent reference. Maybe he thought he was getting rid of me? Well, it worked. The Frisky: Hilarious celebrity pre-fame gigs

Over time, he married and had at least one kid, but I've only learned this through Facebook. No, we don't talk anymore, which is probably for the best.

I do miss his friendship, though: I wish he were still my mentor and my friend, I wish I were in his kid's life, I wish I could introduce him to my boyfriend, who is the best friend and lover that I have always deserved and that I'm going to marry.

But despite all those wishes, with 20/20 hindsight and a lot more maturity, I can see what he did to me was wrong. He should not have rebounded after his long-term relationship collapsed with someone who looked up to him and whom he had a bit of power over, period.

Beginning to date that other woman when we were sleeping together and then telling me about it when I finally verbalized that I was in love with him was just cruel. He knew he was a treasured best friend to me, and he could clearly see that I loved him. Clearly, the Older Man could have handled it better!

Nevertheless, as his former friend, I realize why the flawed person that he is just didn't do that. Maybe he couldn't do that.

TM & 2009 TMV, Inc. | All Rights Reserved

  • E-mail
  • Save
  • Print