I Married My Boss

How it all Began

Was it love at first sight? No. We barely spoke to each other at all for the first few weeks. He was actually one of the people who initially interviewed me and was the one who encouraged the others to hire me. I like to think that he saw past my nervousness that day—I had actually gotten in a minor fender bender a few minutes before my interview.

A few weeks later, I reluctantly started my new sales job at an IT company comprised mainly of twentysomethings. Lord knows how I managed to get a job at a software company as I consider myself to be a “techno peasant.” The first few weeks were torture—learning this company’s complex software was as dry as stale bread. About a month into my job I got my lucky break.

The marketing manager abruptly quit making Josh the new manager, and I one of the lucky ones to get transferred onto his marketing team. I finally got to put my 4 years of university to good use. Josh was friendly, outgoing and eager to help build his new team. He was the type of person who got away with murder; his quirky sense of humour and off-beat comments somehow made him more charming and well-liked by co-workers.

Josh and I sat 10 feet apart from each other but it wasn’t until I was transferred onto his team that I got to know him. Working with him was fun as we were close in age and always cracking jokes and pulling dumb pranks on each other. Josh once left a beef taco in my desk; I didn’t notice until a week later when there were flies swarming around my head.

But seeing as Josh had a live-in girlfriend and I was with my boyfriend of 7 years, we played it cool. However, Josh, always honest, made it clear to co-workers that his relationship was sputtering out. While there was nothing wrong with my then-boyfriend, I always felt something was missing in our relationship.

One day Josh noticed a CD on my desk of a band we both liked. We soon found ourselves having long conversations about music and life in general. Sometimes we would even stay late after work talking. Soon our co-workers (and even Josh’s boss) began noticing and making comments that we should be together. Workplace relationships were acceptable at our company, yet of course still cause for office gossip. We both firmly denied this as we were both in relationships and I would not even consider dating a co-worker, let alone my boss.

Soon I started going for lunch with Josh and his buddies from work, but I just convinced myself that it was all innocent. One day he finally confessed that his girlfriend of 2 years had finally moved out and he was officially single. I felt horrible…well actually, I felt guilty—guilty for sensing a glimmer of hope for us. Not long after, I broke up with my boyfriend. My close girlfriends knew I had doubts for years about our relationship; Josh just happened to be the catalyst for change in my life.

Slowly we started watching football and hockey games after work. Then we enjoyed concerts and movies together. It was a whirlwind romance full of conflicting feelings. We had so many issues to confront very early on in our relationship: we worried about cultural differences—he is of Italian descent while I am Asian; we were apprehensive about dating someone we worked so closely with; and we both secretly wondered if we were “rebounds.”

For once in my straight-laced, strict upbringing, I decided to tell my brain to shut-up and listen to my heart. For every reason I thought that Josh and I should be together, there were probably 3 strong reasons why we should have stayed apart. If you want to see if you and your significant other can live together, try sitting next to each other 5 days a week and still hanging out after work and on weekends. The one great thing about our relationship is that we still wanted to spend time together, even after the daily grind.

Lessons Learned

I learned more about relationships during our 14 months of dating than my entire dating experience combined. Here are a few gems.

Be Open

People often have a “type” of person they are looking for or are attracted to. Or perhaps they have a set timeframe in which they are open to having a relationship (i.e. “I’m going to find a boyfriend once I’m done college.”). While this is perfectly fine, we may be closing ourselves to great relationships with people we encounter now.

If someone had told me 3 years ago that one day I would end up marrying my boss, I would have laughed in their face! But I ended up with a great guy in an unexpected situation because I allowed a relationship to develop.

Be Professional

If you ever find yourself dating a co-worker or boss, try to remain professional at work. Josh and I got away with a lot of things that would be unacceptable in other workplaces because of our company’s casual and laid back environment. Try to leave your personal issues at home—whenever we had an argument, we found the best policy is just to leave each other alone at work. The worst thing is to get in a fight in front of colleagues.

You should also be prepared for your workplace dynamics to change, especially if you are dating your boss.  Once everyone knew we were dating, Josh was no longer allowed to approve my time and conduct my performance reviews, and rightly so. Co-workers may also complain about favoritism. Remember, work is work—try not to take professionally criticism personally. In my situation, Josh was probably harder on me than anyone else on our team.

Watch the PDA

Public displays of affection (PDA) should be severely restricted or eliminated, especially at work. When we first started dating, Josh once gave me a quick peck on the lips in my cubicle. We felt a pair of eyes watching us and turned around. Sure enough, peeking over the cubicle wall was a guy I occasionally talked to with eyes as big as saucers. I tried to bribe him into silence with a free chocolate bar, however he quickly blabbed to everyone in the office that he just saw us kiss. I guess he was not a chocolate fan.

If your relationship is a secret, even going out on the weekends can feel like a clandestine operation. If you live in the city, there are so many prying eyes that it’s almost impossible to go out on a date without being seen. I know of one couple (the guy was a principal at a large accounting firm, the girl was his receptionist) who regularly drove to another town to simply watch a movie together. Although it was a burden in the beginning to hide our relationship, it was also thrilling at the same time.

When NOT to Date

Josh and I are one of the lucky ones because we were able to openly date at work and still maintain a professional relationship with each other as well as with our co-workers. However dating your boss or co-worker is often not an optimal choice. The following are a few red flags for a “no-dating” situation with your boss or co-worker.

• The person is dating or is married. That’s just too much baggage to handle and you may be forever known as the home-wrecker.
• Your workplace does not allow personal relationships, or you may be at risk of getting fired. If you absolutely must date that person, consider quitting or getting transferred to another department before putting your job at risk.
• You’re not prepared to be the subject of some juicy office gossip. Offices are like high school all over again—lots of drama and more gossiping than ever. No matter how professional you may be, people will still talk about you. So be prepared to either face the music, not date, or quit.

Quiz: Is the Situation Right to Date your Boss?

If you answer “Yes” to 7 or more of the following statements, a favorable situation may be brewing between you and your boss. Good luck!

• You regularly talk to your boss about your “type” of man/woman.
• You often go for lunch or coffee breaks together.
• You feel comfortable talking to your boss about both personal and professional matters.
• You have caught your boss looking at you and then quickly looking away.
• Your boss treats you with respect and often compliments your work.
• Your boss is single.
• You both have suggested hanging out after work.
• You have many common interests.
• Your boss is trustworthy.
• You believe your boss will maintain professional relations even if your relationship does not work out.