Rule #31- That Awkward Moment When You Run Into Someone You Used To Date

via Intense Moments on the Streets of Vienna, russavia

A couple of weeks ago I was strolling along, minding my own business and fumbling around for something in my bag. I look up, and  lock eyes with this guy I went out with a couple of years ago (if you haven’t read the post about this particularly awful date, do so now). Not having enough time to duck behind a rubbish bin or a parked car, I was forced into a very awkward, very smiley conversation with him.

There is no strict protocol about what to do or how to behave when you run into someone you once went out with. The harder the break-up, the harder the accidental run-in (here’s to hoping you aren’t stalking them and haven’t orchestrated the whole thing).

I personally become over-smiley and laugh way too much; but to be fair, this is how I choose to deal with most awkward situations.

You’ve pictured this very moment in your head (about a million times); you’re always wearing a sexy red dress (and are possibly sporting an awesome new pair of boots/hot guy). You smile casually, say hello (noting happily that he’s put on weight and his new girlfriend is in no way prettier than you).

But in reality, you are probably going to run into him at that precise moment that you’re late for work, just got into a huge fight with your mother, and haven’t washed your hair in three days.

Rules For Bumping Into An Ex:

1. Things you should NOT, under any circumstances, do:

A. Veer of course and “casually” dive behind a dumpster; your’e not fooling anyone! Don’t hide or ignore them; you are better than that!

B. NEVER ask: “so… are you seeing anyone?”

First of all, you don’t really want to know if he is. Secondly, it’s the worst kind of small talk imaginable. Also, and most importantly, he may misunderstand and think you are interested!  Which can either lead to him turning you down, or even more awkward, him calling you. 

C. Don’t flirt! 

DDon’t talk about the amazing new guy you’re dating! It’s disrespectful and not very nice (yes, I know he was the one who dumped you! But he’s now fifty kilos heavier, and unemployed to boot. So no need to rub it in).

E. Don’t be mean or spiteful.

F. You had a nice chat, you smiled just the right amount, you are almost out of the danger zone. And then, as if out of nowhere, you blurt: “We should really get together sometime”.  You don’t want to hang out, you don’t really ever want to see him again; it just seemed like the polite way to say goodbye.


2. Keep the conversation short, simple and friendly.

Just say hello, be polite, inquire about his health, and then you can get the hell out of there.

If you really can’t face him, for whatever reason,  just smile when you walk past (acknowledge him) and keep on walking.


  1. Awkward moment…seeing ex-wife at the bank 2 years after divorce…No feelings just thoughts. Gee you put on about 50 lbs. That guy you were messing around with has been feeding you well. Gotta go and haven’t seen her since (20 years).

  2. Ooh love the subtle shout out to The Lady Eve with pic 5. Hilarious advice on dealing with an ex there: just pretend you’re a different person and brilliantly fake a British accent. ;-)

  3. hahaha! I fucking love this post so much because I just bumped into my ex man friend, Sir Henry, a few weeks ago. BUT, I was totally dressed to impress, on my way to see a client, and it couldn’t have been a better meeting!!! In fact, all that I heard was my laughter and click click click of my Kate Spades as I strutted away from the scene of the crime. :)

      1. I just started laughing! And kept walking! It was super hilarious. He’s been text messaging me ever since. Can’t say that I’m not pleased… but I refuse to be “pleased” in the formal sense (not that he’s offering, but I’m sure that would take little nudging).

      2. It’s amazing how when we run into someone we used to go out with, we tend to get slightly nostalgic, forget about all the bad things, and are tempted to reconnect with them.

      1. Hahaha but that was like four seasons and a film later. Also, I kind of felt like the Steve in the film wasn’t the same Steve that they had in the show, the whole cheating thing felt very out of character

      2. Yes. In the film, I feel as though he was “entitlement” steve… married to the big earner, thus he deserved more, including sex. In the series, he was good guy Steve… someone that I would have dated happily!

  4. Just to FYI from a guys perspective, if you are being “overly smiley” we will misinterpret that about 99% of the time as you showing interest, which may lead us to ask you out or something. Just be professionally friendly, like you are meeting someone in a business meeting.

  5. the last time i saw my ex was at a mall and she was too far away to say hi to. but i dread these situations. i imagine these scenarios – her looking hotter, or worse, her walking with her new boyfriend or worst, her husband. i still have a strong feeling for my ex, even though it has been almost three years since we broke up.

  6. haha last one caught me walking on the road wit a bag of fries in my hand – looking like a real hot mes *shame face* laughed it off kept my cool and even offered him on … then after I walked off I realized my knees were shaking like crazy. DAMN

  7. cool post, like the light touch. thanks for visiting thewavewithin. ps, something about having a surfboard under your arm makes seeing ex’s so much easier…

  8. I actually saw my ex on a night out the other day, he was joining a friends bday party where I was invited also.As soon as I saw him coming into the venue I told my friend I was sat with that we should move.So i moved and walked outside then it was freezing so came back inside to the bar with my bar at the bar so I couldnt see my ex. Shortly my friend told me he had left! I felt a great feeling, neither did I see him at a close distance or say hi. And the best thing as that I didnt care! It was great-I just hope I never ever see him again! And I wish the birthday boy had told he was invited and then I would never have gone!

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