A Jewish Matchmaker’s Guide to Mixing Business with Pleasure

There is something ultra-enticing about an office romance. Those long gazes across the conference table, the innocent brush-by of shoulders over the printer, that sharp pang when you realize you actually like this person…. and when you realize the feeling is mutual…pure bliss! Isn’t this how great love affairs begin? Well, maybe – and maybe not.

Ask almost anyone about workplace romances and they will warn you against them. What could be more painful than breaking up with someone that you will see on an almost daily basis? And what if he/she starts dating someone else in the office? Ouch! But…then again…what if this one turns out to be different? What if the two of you are perfect for each other? What if you are both serious and no one is playing games?

Hence, the dilemma, and unless you have a herculean willpower it’s probably wasted reflection, because honestly, what is more difficult to resist than physical and mental attraction to another person?

So with the understanding that this flirtation is probably going to lead to more, let’s map out some guidelines for making it happen with the least painful of consequences with the focus being on keeping your job, your dignity, and your sanity intact.

Stay in professional mode. In other words, when you’re at the office, don’t act as though you are dating. Address each other professionally and maintain a professional body distance. This is not the place for PDAs, and acting lascivious in the workplace will do nothing to enhance your professional reputation. Instead, let your professionalism shine by keeping your personal life, personal.

Inform the higher-ups. If this relationship really takes off, you need to inform your supervisor – especially if the two of you work in the same department or for the same person. Make it clear that you are committed to your job and that you will not let the relationship interfere. There is no reason to keep it a secret from your co-workers either. People are going to find out, and being open about it will keep the gossip to a minimum. If you follow tip #1, the buzz about the two of you will quickly die down as co-workers see that you are not letting your heart influence your work ethic.

Meet for lunch sparingly. Although the extra time together in the middle of the day is exhilarating, resentment in the workplace can easily build-up if the two of you create an “us against the world” vibe. Let other people in. Do your best to keep your lunch routine the same as it was before the two of you started dating, and keep your lunch trysts to no more than once per week.

Don’t bring your relationship to the office. Do NOT bring your disagreements, hurt feelings, jealousies, etc to work. Agree from the beginning that you will put aside ALL differences when you are in the office. Don’t glare at each other and don’t give each other the silent treatment, Act professionally no matter what issues you may be working through. Hash it out when you get home, but spare your co-workers the negative vibes.

Don’t date if it’s against company policy. Again, a herculean effort may be required here but if one of you loses his/her job, the resentment could be insurmountable- not to mention financial and other stressors. If you are willing to lose your job for this person, do it at the beginning. Let one of you resign from the company and find another place to work, so you can date freely. Sound intense? Not as intense as being fired from a job you love over a fling.

Have a contingency plan. If you date a co-worker, there is a good chance that the relationship will eventually end. Have a contingency plan for how to handle that possibility. If working together after a break-up will be misery for you, make the choice not to date right now. Wait it out. Don’t feed the flames by saying “never”, but give it a few months before you pounce. At the very least, get to know this person better as a friend, and if there is something real and lasting, it will only get stronger and more resilient, and therefore, better able to weather the possible storms of a workplace romance.

Sign up for my Monday Marriage Tips!