6 Tips to Pull Off a May-December Romance at Work


Believe it or not, a lot of younger women meet the older man of their dreams at the office. After all, you’re spending a lot of time together and there’s a good chance that you have common interests if you’re both working at the same place. But if you’re not careful, getting involved in a May-December romance at work can get tricky, especially if he’s a higher up in the company, like a president, manager, or even just your supervisor.

If you’ve got your sights set on a handsome, mature man at work, you don’t necessarily have to write off the idea of a May-December romance with him—at least not right away—just because you’re colleagues. There’s a certain way to go about it in order to ensure that you salvage your career and get the guy. Here’s what you need to know to pull it off:

• Make sure it’s worth it. Is this May-December romance something you really want, or are you just in it for the thrill of the chase? With office romances, there’s always the risk of it ending badly for your career, so make sure that it’s something you really want before taking the risk.

• Make sure it’s mutual. This might seem like common sense, but it couldn’t hurt to stress. Before pursuing any sort of May-December romance with a co-worker, make sure that it’s something they’re interested in, too—some people just aren’t comfortable mixing work with pleasure. Test the waters by asking them to join you for something that isn’t work-related, like lunch or a party on the weekend. If they don’t take you up on the offer to spend time together outside of work, they’re probably not interested.


• Check your company policy. Every company is different—some workplaces might just frown upon office romances, but others officially ban co-workers from getting involved with each other.  Before pursuing a May-December romance with someone you work with, find out what the rules are. If there are no formal rules in place about co-worker relationships, try asking around to find out how acceptable it is within the company’s culture. Don’t just come right out and say you’re interested in pursuing a May-December romance with one of your co-workers, but ask if any employees have ever started dating within the office. You’ll be able to gage pretty quickly if it’s something that’s appropriate or not. This also goes back to the first point; make sure it’s worth it.

• Be prepared for awkward moments. And know how you’re going to handle them. Imagine having to work on a project with someone you’re secretly sleeping with, or having to cross paths with them every morning if the May-December romance doesn’t work out. Have a plan in place for dealing with these kinds of situations.

• Keep your private and professional lives separate. The whole office doesn’t need to know that you’re a couple after business hours. Be discreet about your May-December romance and avoid public displays of affection at work or at work-related events.


• Mind your social media networks. If you’re trying to keep your May-December romance private, don’t post cozy pictures or share racy comments about your relationship. Even if you aren’t connected to anyone else from work, publicly posting stuff like that can easily be found and used against you.

What do you think: Do you have any other tips for getting involved in a May-December romance with someone from work?


Rosato, D., “How to Keep an Office Romance from Destroying Your Career,” TIME web site, July 14, 2014; http://goo.gl/E73Iqv.


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