Close Encounters of the AWKWARD Kind

ex boyfriendIt was bound to happen sooner or later.  In a city the size of Philadelphia, there are only so many single men, so many bartenders and so many routes one can take from Old City to South Philly.  This is the problem with dating locally— or perhaps with serial dating, come to think of it.  All I know is that after my little “encounter” earlier this week, I need to either A) stop dating or B) go back to long distance relationships.

Let’s start at the beginning, shall we?

A friend from the Philadelphia Writer’s Conference invites me to join him for a meeting in Old City.  It has something to do with civic engagement and the arts and since I’m still struggling to develop a life beyond, I say “Sure, why not?”

(Additionally, there are going to be free drinks.  As such, this is a no brainer.)

I’m wearing my very best power outfit: floral print dress, red heels, red scarf, red chopsticks in my hair and red earrings, all paired with a sober black blazer to lend the ensemble some modicum of seriousness.  I know I’m looking fierce because on my way to Old City, I pass a very well-dressed, statuesque African American woman who is also wearing a killer power outfit and she says, “Great dress!  You keep on walkin’, girl!”

When a woman this appointed gives you an unsolicited compliment on your outfit, you know it’s good.

I arrive at Trust, the bank-come-art-gallery where the meeting’s taking place, and spot my friend by the bar.  As I make my way through the crowd, I breathe a sigh of relief.


Well, Trust is in Old City and Old City is Bovary-Reading-Bachelor territory, just as Northern Liberties belongs to Date #17 and Passyunk to the Man from Marshalls.

Given my taste in men, I wouldn’t be at all surprised to find a former date at a meeting on civic engagement and the arts and given the venue of this particular meeting, I wouldn’t be surprised if that former date was the Bovary-Reading-Bachelor.

“It’s so good to see you!” I tell my friend.  We talk about agents and manuscripts and day jobs and I finally confess, “I was afraid I might run into someone…”

“Oh?” he asks.

“Yeah.  A former date.”

“Don’t worry,” he assures me.  “I’ve got your back.  If he turns up, I’ll create a diversion and you can make your escape.”

“Sounds good,” I smile.  It’s not that I’m afraid of running into my previous dates it’s just that it’s never actually happened to me before.  My exes are all in different states or different countries.  I don’t know the protocol.

The meetings goes off without a hitch—by which I mean the Bovary-Reading-Bachelor does not show up– and my friend and I spend the next hour or so whisper snarky comments over our drinks.

It’s not until I leave that I see him.

He’s half a block away, heading down the sidewalk straight towards me.  I recognize him immediately and he looks no less tortured than he did when we first met at Fork several months ago.  He’s wearing jeans, a button down shirt, and carrying a messenger bag.

I know he sees me: I’m wearing red heels!  We’re the only two people on the sidewalk and he’s just a few feet from me now.

I’ve always dreamed about running into an ex-boyfriend while dressed to kill.  But he’s hardly an ex-boyfriend; he’s simply a man I once dated so the way I see it, there’s no need to cause a scene.  No need to go stomping off in the other direction.  No need to ignore him or say something vindictive or go all Shakespearian on his ass.

And so, upon deciding that a simple “hello” should be socially acceptable considering the circumstances of our acquaintance, I glance up into his face and say “Hi.”

He says nothing back.

He doesn’t even stop.

In fact, he continues right on down the sidewalk as though he hasn’t even seen me.  And like I said earlier, I’m wearing my red-f*cking-high-heels.  How could he not see me?

Intentionally, that’s how.

Math has never really been my thing but statistically speaking, this sort of thing is bound to happen again.  I like Old City.  I like NoLibs and I’d like to think that two rational adults could at least acknowledge one another’s presence when crossing one another on the sidewalk.  Is this too much to ask for?

Having never dealt with local exes before, I’d love to hear your stories.  Surely I’m not the only one who’s experienced this sort of thing?

20 Responses to “Close Encounters of the AWKWARD Kind”

  1. Jess Killmenow

    Well, we could go into a pyscho-thriller safari here, I mean, it is tempting to try to analyze the once-dated’s thoughts, but since those possibilities are literally endless I will not attempt to do so in this box. The point being: there is nowhere to go, there. You can only analyze your own thoughts. I commend you on behaving well (with courage) in a moment you charged with inordinate importance. Bound to have happened sooner or later, no?

  2. Jess Killmenow

    But you asked for stories! My worst story is meeting an ex-girlfriend in a coffee shop while having coffee with my fiancée and being enthusiastic to her about our recent engagement. At the time I didn’t realize how cruel I was probably being – that I should have said a quiet hello and gone to sit done with my bride to be without fanfare. But let’s look forward, shall we?

  3. mairedubhtx

    This is just me, but if I saw my ex-husband on the street I would run FAST in the other direction. When I first moved back to San Antonio, I was so afraid of running into him (and we drive cars and never walk) that I refused to drive on the road that led to our old house 18 miles away. This sort of means I never want to see him again.

  4. kortni24

    I worked with my ex for a few months after he cheated on me (makes it even ten times worse when it ends that way), and some days we would get through with pretending like we never dated at all and were just coworkers.
    Other days… he would try to say hi, and I wouldn’t even look his way, especially when it was during the days after his current fiancée stole his phone to text me and rub it in my face.

  5. Dennis Hong

    I run into exes all the time, but that’s cuz I’m pretty good about staying friends with them (hence, one of them writing on my blog).

    I do have a good online dating anecdote, though:

    Once, while I was out to dinner with a girl I met through eHarmony, I got recognized by another girl I hadn’t met yet, but had been corresponding with through Match. I know this because, in an email a few days later, the Match girl asked if I was at a certain restaurant the Friday night before, because she saw someone that could’ve been me.

    How’s that for awkward?

  6. Jill

    Yikes. I’d drive the other way to avoid an ex-husband (if I had one). I have refused to allow an ex-boyfriend to say hello to my then-toddler daughter, I couldn’t stand him that much. But in this case? You were right, he was rude and immature. His reaction sounds like junior high, and I should know, I hear about it every night. But for stories? 7 years ago we moved to my husband’s home town. I meet his ex-girlfriends all the time, and so far everyone’s been a perfect grown-up. Although after a few months I did ask him just how MANY there were, anyway?

  7. Rachel

    He is immature. Had a similiar experience – I see him about twice a year, and every time he makes it a point to say hello, asks how I’m doing, and then we move on. It can be awkward, but just to pass someone like you don’t know them is ridiculous! (Understanding that it is different for people that you were in a serious relationship with like engagements and marriage.)

  8. Grey Goose, Dirty

    I actually dated 2 guys in college (more than one or two times), that after we stopped seeing each other, I would still run into. BOTH of them acted like they had never met me before! Literally one said, when I went up to him to say hello at a party ‘have we met before?’ and then proceeded to introduce himself. I think everyone around me heard my jaw hit the floor.

  9. sarahnsh

    I had this one guy I came across in my English class when I was still dating my long distance boyfriend. We flirted a bit, and then at the last day of English class he ended up telling me if I didn’t have a boyfriend, he’d want to date me. I think he was thinking I’d make a move, but I was in a relationship, so no. I came across him later working somewhere, and he never said anything. I went there again, looked him in the eye, mouthed ‘Hi’, waved, and he ignored me. I ended up avoiding that place and I still avoid it to this day.

  10. Katie M

    I can top all these stories. I have a bunch but here are two. I work in a coffee shop and after 9 months of flirting with this one customer we finally went out. We went out on a few dates but we got in a fight via text messages (mature right? did I mention he’s 31?) and it ended pretty badly. After that he pretended I didn’t exist, even when I had to take his order. He didn’t even have the decency to pick another shop (there are a billion) or pretend to be civil. He was even mean to my other female coworkers. THEN not long after that he started bringing in another girl, who always looked like she was in last night’s outfit. Nice right?
    Another time, I had a one night stand, yep, super classy. We had a bunch of mutual friends and another night we ran into each other at a bar while I was with said friends and he introduced himself to me. I was taken so off guard I actually blurted out “Did you REALLY just introduce yourself, AGAIN?” and watched as recognition dawned in his eyes. Then there was the most awkward silence I’ve ever experienced while he was embarrassed and I was hurt and angry. Wonderful, right?

  11. amy mac

    Haha nope you are not alone! After my freshman year in college, I had a particularly awkward break-up, and while I was out with my mother at the store, (…) lo and behold, I see him coming down the aisle with a full cart. What to do??
    My mom, completely oblivious to my conundrum, is trusting me to push the cart, and I don’t see how I could just bolt. So I bear down, preparing to smile politely and say hello. However, he gets a look at me, turns right on his heels, and runs down the aisle, leaving his full cart abandoned behind him.
    At first I was horrified, embarrassed, and hurt–and had to endure my mother telling everyone the story of a young man who’d high-tailed it down the aisle, leaving even his MILK behind–but I eventually came around to relief. Who wants to date a guy like that??

  12. aka gringita

    I’m reading your post, and the comments, and it’s just confirming what I already really strongly suspected: Guys are boys, and boys are stupid. 😉

  13. Amanda

    So last night (after reading this) I was shopping at a sporting goods store and caught a glimpse of a guy I went on 2 dates with last fall. I quickly darted down an aisle to avoid him – I had rudely ignored his texts after the second date instead of politely telling him I wasn’t interested. In the end I was rewarded for it. I immediately headed to check out instead of lingering in the store and the lady in front of me in line handed me a coupon for $10 off that she couldn’t use. If I hadn’t been so intent on running from that guy, I wouldn’t have saved $10!

  14. The Kitten that dates

    oooh I have the BEST run into Ex story!!!!!!

    I date my ex, Lamo, for 5 years. We had been broken up for 6 months. I was with the new guy walking through home depot, when I saw Lamo standing there with a new woman and his son. He tried to avoid my eye contact and when I turned down and isle, I think he breathed a sigh of relief. Until I said to myself “self, screw this! Go say hi” I turned back, popped back around the corner and said HI! Glad to see you have finally moved on….

    It was priceless!

    ps… I just moved from WI to Philly, but I live in the burbs. Its way too hot here.

  15. becky119

    Hmm…I think my favorite would have to be when I broke up with my ex, Mike. I still get angry when I think about him. You see Mike cheated on me when I was in Germany BUYING HIM PRESENTS! I come home to a very strange voicemail from one of Mike’s friends that I couldn’t quite hear. Mike told me that his friend was playing a joke on me and naiive little me believed him. Then we signed a 6 month lease on an apartment. Two months into us living together, I found out the truth and broke up with him. But I couldn’t afford to move out and continue to pay rent so I was forced to share a one bedroom apartment with an asshole who cheated on me.

    Then I met Adam. And I offered to cook him dinner at my place (which he knew I shared with Mike). So I was cooking dinner for Adam which usually chicken breast comes in packs of three or more, so I made three pieces and figured I’d have leftovers. Once dinner was done I put the extra piece away. Then Mike came home while Adam and I were ‘watching a movie’. He later made a snide remark about how he saw that I left him ‘pity chicken’ but that he didn’t want it.

    I ended up moving in with Adam for the remainder of the time that I was supposed to be living with Mike. I kind of broke him…Mike ended up dropping out of school and being committed to an institution by his bi-polar mother where he received electro-shock therapy. And no, I’m not making this up.


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