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


In “King” George Strait’s song, "All My Ex's Live In Texas," he talks about how he keeps running into his exes wherever he goes. And like King George, we've all had the unpleasant experience of running into an ex when we least expect it. It can be unsettling, to say the least..

When we think of an ex, we usually associate the term with a former romantic partner. However, the ex doesn't just have to be a philandering cowboy. It could be an ex boss, an ex coworker, or even ex family member who is no longer in the picture due to divorce.

Whichever ex you happen to run into, the encounter can be stressful. But before you bury you face in your jacket collar to hide away, check out my 3 quick and dirty tips for how to handle a run-in with an ex.

Tip #1: The Romantic Ex

Let’s start out with the most popular of the exes – the romantic kind.  

You remember that relationship where every day felt like your birthday? You and your special someone walked hand in hand feeling like a fairy tale? Well, turns out they were wrong for you in every which way. And suddenly, the ex from hell, who has been out of sight and out of mind, just sat down at the table next to you at a restaurant.

Say it with me, “Awwwwkward!”

So now, as much as you'd like to bury your head in your caesar salad to avoid eye contact, you can't stare at lettuce leaves forever. You’re forced to make small talk. As a manners professional, I never recommend lashing out (especially in public), but fleeing the scene isn’t the answer either. To save face, you need to act as maturely as possible, even though deep down you want to throw a drink at their smug face.

When I think of exes and how best to cope with them, I remember a great quote by comedian Louis CK regarding divorce. He said:

"Divorce is always good news. I know that sounds weird, but it's true because no good marriage has ever ended in divorce.”

As a happily married man, even uttering the word divorce makes me ill.  That’s the last thing I ever want. But I see his point. There’s a good reason why the person sitting at the table next to you is an ex. So even if they deserve that drink thrown in their face, what would be the point? They're already an ex and there's no sense in dredging up the past.

The best approach is to be cordial and take control of the conversation. Doing that allows you to control the level of awkwardness. Start it, end it, and be done with it, on your terms.  Say something like, “It’s good to see you…Small world…I hope your family is doing well…Good to hear.” Then return to your meal and initiate a conversation with your current dinner companion. Play it cool, be an adult.

If something deep down inside tells you to get back in touch with the ex (for whatever reason), do so at a later date. But for now, at this particular instance, your time is more valuable than the “What if’s?” that come with an ex. 

Tip #2: The Ex Family Member

As a child of divorce (my mom married three times and my dad married twice), I am very familiar with bidding farewell to family members and not knowing if I’d see them again. It’s sad, but it’s a part of life.  

As a child, I had no control over whether or not I got to see former family members again, but as an adult, it’s truly up to me whether I want to keep in touch with ex relatives. And I do. In fact, just last month I had dinner with one of my ex stepfathers. It was great to catch up. However, that interaction was planned and agreed to by both parties. It's very different than randomly running into someone you used to call family.