Flash Friday: What’s the 40:20 on Dating in the Workplace?

Welcome to the first Flash Friday. On the first Friday of every month Molly Ford of Smart, Pretty and Awkward and I will answer a question from both the 20-something and 40-something perspective. The question today:

What is your advice on relationships in the workplace?

FLASH FORWARD: Molly’s 20-Something Advice:

For many 20-somethings, your twenties are focused on two main things: finding a job and finding a mate. Most activities are divided between work and dating, but sometimes these circles do cross.


If you find yourself interested in someone at work and believe your affections are returned, the first thing to do is to consult the company Human Resources manual to understand the dating disclosure policies. These politics usually vary depending on how closely you work with the person and if there is a subordinate relationship involved. Checking out the dating politics via the HR manual can be done discreetly as every employee should be able to access the manual without causing suspicion that you’re breaking rules.


Eva, a 20-something reporter, echoes, “Legality first. Before you start day dreaming about the future with your office crush, figure out if you are even allowed to date via your office policy.”


If office dating is allowed, you are free to enjoy the new relationship from a legal perspective, but not necessarily from a career standpoint. It can be awkward if the person you’re dating is also the person that reviews or has the power to promote you.


Isabelle, a 20-something student, says, “Even if dating is allowed, never date your boss. Never. If you want to date a co-worker, think about how your relationship will change if one of you gets promoted.”


Rebecca, a 20-something account coordinator, wonders, “Are flirting emails via the work server okay?” Besides this question, ask yourself: Do you want to get lunch together alone everyday? Do you want to tell your co-workers directly, or let them figure it out on their own? How often will stop by your partner’s desk? If you have dinner plans, will you leave the office together at the end of the day? Answer these questions with your partner so you are both on the same page.


This discussion, and the decisions that come out of it, are paramount. Ben, a 20-something finance professional answers, “Having had a few office romances, the first thing I can say is: you need to set guidelines. And actually stick to them.”


If office romances are not allowed, or are not allowed without disclosure, you are at a place where you need to decide how to proceed. It’s a personal choice to decide whether to disobey the HR manual, and also when or how you and your sweetie want to disclosure the relationship to HR. Every situation is different, but risking losing your job over what might only a fling is poor planning.


Eva, the 20-something reporter, sums up by saying, “If you are going to make the leap and date someone from your office, make sure you are both serious and on the same page about the relationship and where it is headed.”


FLASHBACK: Christina’s 40-Something Advice

Workplace romances were as common 20 years ago as they are today. And with only 1 in 100 American companies having policies against dating, don’t expect it to go away. How did 40-somethings handle it?


Some women ended up marrying their office crush. Their advice, “When the relationship gets serious, one of you should get going”. In this case, discussing an exit strategy is key…and that can be tough. You have to be honest about career goals and who’s more likely to succeed at the company. Should you decide to both stay, keep the sweet nothings at home. Almost all 40-somethings agree:  “There’s nothing worse than seeing a couple getting all lovey dovey at work.”


On the other hand, a lot of 40 something women came through office relationships feeling the risk was greater than the reward. Sara, who worked with a lot of people her age, found it was easy to get involved. But nothing was more cringe-worthy than having her manager comment on her relationship. She felt it affected her long after the relationship ended:

“Too often personal issues get dragged in front of senior managers or co-workers. I can say from experience, it often turns into something you wish you hadn’t done. Just be the mysterious, smart, funny girl who leaves work at work. Grab drinks with a girlfriend after hours. You’ll be glad you did! You never know when you’ll want a reference – make sure it’s glowing!”

Rita, a human resource director, agrees it does get talked about. While it’s not something her company prohibits, it’s something they need to be aware of:

For HR, it’s a liability. We don’t disallow it but we have to protect ourselves against sexual harassment suits”.

She sees it come into play even when the couple does their best to keep it separate:

“I’ve seen it cause conflicts. When something upsets you, even at 3:00 AM outside work, it’s hard to keep separate. I’d say don’t date at work, at least not recreationally.

Deborah, a 40-something marketing director in companies ranging from start-up to sports management, admits to dipping in the company well a few too many times. She counsels, ‘do what I say not what I did.’

“Having had four workplace relationships – it’s never good. If the relationship ends, and more than likely it will, there’s often an awkwardness that can be detrimental to one’s progress, particularly if you have to work closely with that person.”

However, she has some suggestions for bending the rules.

“Make sure the person doesn’t work in your department, you don’t report to them in any way or vice versa. Establish ground rules up front about how public you will go. You can’t discount the excitement you feel when you secretly date someone at work, but it can negatively affect you in the long run if you can’t act normal around them. Try to act as professional as possible whether or not people know.”

Caroline, a Sr. Designer Director urges you to consider whether a casual hook-up is worth it.

If you are looking to build a strong career based on solid reputation and good work ethics, “hooking up” is an absolute no-no.  Beware the office party. Normally reserved people have a few drinks and the next thing you know, Sara from design and Jim from accounting are having way too much fun dancing. It’s the stuff office gossip is made of. Don’t be Sara!

I would add that if for some reason you do get a little too rambunctious at the office party, don’t make it worse by talking about how embarrassed you are. Hold your head high, apologize to the appropriate party if needed and then move on.

Happy Flash Friday!



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