How to Handle an Awkward Ex

Whether it's a former lover, former family member, former colleague or boss - here's how to handle the unexpected run-in with an ex.

Richie Frieman
5-minute read
Episode #314

When it comes to accidental run-ins with former family members, the key is to not dig for answers.  For example, if I run into the son of an ex parent, the last thing I'm going to do is dig for gossip. For one, it’s rude and none of my business. And secondly, I know that they will report everything I say back to their family. So it's important to be careful and respectful. Starting the conversation with, "I hear your mom got divorced again…" will reflect badly on me and for what? What do I gain by continuing the tradition of infighting?

Make seeing an ex family member as easy and elegant as possible. Don't dwell on the past while in line for a Frappuccino. 

Tip #3: The Corporate Ex

Hands down my favorite ex of all time is the corporate ex.


Well, there’s no baggage like with the romantic ex and there’s no bloodline connection like the ex family member.

A corporate ex is simply someone you used to work with, or for. Maybe when you worked with them, you were intimidated or annoyed by them. And maybe inside the walls of that office, they were King or Queen.

But that has all changed. This person no longer has any power over you. It’s like a bully who used to give you noogies in grade school, until you hit puberty and then towered over them. Things change, time goes on, and now you owe them nothing more than a simple nod of acknowledgment.

In my book, Reply All…And Other Ways to Tank Your Career, I opened with a story about the horrible boss at my first job. I was 22 and knew nothing and he took advantage that naiveté. I haven’t seen him since the day I quit, but when a message from him popped up on my Facebook page, I really wanted to ask him how business was going. I knew that it failed, but I wanted to hear it from him. And deep down inside, I hoped that he would say something like, “Sorry I treated you so badly.” But he didn’t and probably never will. So instead of getting bitter, I simply deleted his message and went on with my life. 

The only connection you have with an ex coworker or ex boss is a paycheck from the same company and an interest in the same industry. Other than that, you shouldn’t feel obligated to give an ex colleague more than a moment of your time. Simply wave, smile, and keep on walking.

When you really think about it, there is no hard and fast rule about who you should and shouldn't talk to. Ex-friend, ex-family member, or ex-lover - it’s up to you to decide who will be in your life.

As always, if you have another manners question, I look forward to hearing from you at manners@quickanddirtytips.com. Follow me on Twitter @MannersQDT, and of course, check back next week for more Modern Manners Guy tips for a more polite life.

Do you have any recent graduates in your circle, or perhaps someone who is looking to start a new career, check out my new book, Reply All…And Other Ways to Tank Your Career for great tips and advice on job success. It's available now!

Scared man, awkward moment, and break-up images courtesy of Shutterstock.