Do Tell: What was Your Most Awkward Ex Boyfriend Meeting?

Last winter, I took my dog out late on a Saturday night. My hair was in pigtails, I had no makeup on, I was wearing my glasses, my boyfriend's winter coat, slippers, and pajama pants with monkeys all over them.

I was right out front of my building. The dog made a poop and as I was picking it up with a plastic baggie, my ex-boyfriend and his new wife walked by. Ugh. They stopped and said hi and we were all civil.

I was TOTALLY over him, had been for years, but I wish I hadn't looked ridiculous, with a baggie of turds in my hand.

That's one of the dangers of living in the city, I suppose. People walk by. All day and all night.

Ha! I saw my ex-boyfriend at a restuarant Saturday night. Lets just say I was dumped because he felt he was being used, blah, blah, because I was content with the way the relationship was. I'm not the marriage kind of girl. Don't get me wrong, I think marriage is great for other people, just not my thing. I'm selfish I guess. And probably have some underlying commitment issues, who knows?

Anyway, he came over to my table with me and my friends to tell me he was getting married. My response was "Great, congratuatlions!"

And he sat there awkardly for about 3 or 4 minutes, finally he said, "Nice seeing ya." And we exchanged more cordial words and he walked away.

My friends all were looking at me with their mouths open. Apparently this was not the proper reaction to -- I'm getting married. They told me he looked a bit hurt, by my reaction. I'm not sure what he and or them wanted from me.

My most awkward meeting wasn't awkward for me but for his new girlfriend. . . I was on my way to a dinner date (so I was looking very cute) and I had like 30 mins to kill before I met my date so I ran into costco and there they were shopping . . . . I later found out she was so embarassed she was wearing joggers (not even cute ones) but like raggy gross baggy not attractive in the least joggers and jacket and my ex just stood there and was introducing us. I did feel bad for her but at least it worked to my benefit!LOL

My most awkward time- I was at the bar in my hometown and saw some of my ex-bf's friends. I was saying hi to all of them and they go 'Oh- that funny your here becuase Jay (the ex) is here too! (he had moved out of state like 2 years ago). So it was sooo random. Anywho, when I finally stumbled across him- and his WIFE- he was speechless. While he was in shock, his wife was so nice and talking to me about everything and saying 'Oh Jay talks about you all the time! And he says when I wear this certain lotion that it reminds him of you!'.....umm....shouldn't he be over that by now?? strange.

I ended up going out to lunch with one of his friends (ted*) because we worked in the same building and my ex (bud*) ended up seeing us there. Bud was saying that I was the one who was ruining their friendship (I guess Ted was getting distant with Bud at the time) and that I was a rotten person for dating his close friend.

It was really an innocent lunch. Needless to say, we have been dating for four years and it still cracks us up to this day when we think about him accussing us of dating.

ps: We were really repulsed by the idea of us dating at the time! And I did look cute that day I must say.

I remember in grade 9 shop class I had been using the rip saw to cut a really small piece of wood. Not paying attention (as my crush walked in), I ripped through the wood, as well as my hand. My project was ruined and there was a massive gash between thumb and finger, that actually brought me to a few tears.

Last year, my junior year of college, I went to a gay bar with one of my newer guy friends, and he ended up pulling me up to the bar and going "you have to meet this guy I'm seeing now!" and introducing me to his new boyfriend, who was also one of my first boyfriends, from like sophomore year of high school. I had to have a handful of shots to get over the shock. We're all buds now.

Sweet Jesus, annebreal, I'm not sure that story can be topped. I certainly can't beat it!

Yeah, annebreal wins!

My most awkward was when my old, longterm boyfriend came to my mother's wake. My fiance was with me and we were standing up near the coffin when I saw the old boyfriend walk in. All of these heads looked at him, then at my fiance, then at me like they were expecting a fight. It was a little uncomfortable when the 3 of us were standing there and I was making introductions, but it was even more awkward because it was right in front of the casket. Very odd memory.

I was working fast-food. He walked in and looked a little startled...I smelled like fried food and looked a mess as I was on kitchen duty that day. Horrifying.

I remember this so clearly it happened in slow motion. I ran into my first ex boyfriend at a bar in Berkeley one night before Christmas. I was there with 2 of my guy friends and my sister and her best friend. We were all dancing and I looked up and through the crowd I saw him approaching. I froze literally on the spot - a doe caught in the headlights - and not knowing what to do, drank my entire drink in one quick sip. Luckily my sister had spotted him the second I did and without thinking she grabbed my hand and yelled "Go!" Her best friend was pushing me from behind, yelling, "I got the jackets!" Three seconds later we were panting on the sidewalk. My guy friends in the bar said that my ex pounced on them at the bar and asked where I had went, they looked around and literally were amazed because I had vanished. Of course they called me and met us at a bar down the street where we all took a victory shot before heading home. Didnt want to run the risk of seeing him again.

wow party, thats impressive!

I'm actually going out to lunch with my ex bf tomorrow, BUT a few months ago I went out to a bar to celebrate the promotion of a friend, of a friend of a friend who worked at the same company as my ex. My roommate said as we walked in, oh you KNOW (lets call him Jeff) will be here, I said no, you're crazy there are like 2,000 employees in his office, what are the odds. We go the WHOLE night and I'm standing at the bar closing out my tab when I look to my left and low and behold there's Jeff. Go figure. I just laughed.

I had a VERY akward encounter...
It was February 13th, and I was downtown to meet a friend. At my ex-bf´s department corner, my cel rang, it was my mother letting me know I had won a Valentine´s dinner (no kidding). As I´m about to turn, I see my ex-bf with his new girlfriend... You shoul´ve seen my face... you should´ve seen HIS face! I wanted to die... He went up his apartment with her and in less that 2 minutes he was down where I was. A few days later it was my birthday, so the shamless man insisted on buying me a birthday present... which he did! He took me to a bookstore and insisted on buying me a present, even though I was crying and telling him not to... All in all he stayed with me for about 45 minutes, I was crying all the time LOL (it was all to recent, I had learned he was with someone else just a month earlier and, before that, he called me every now and then to see how I was doing and everything). His girlfriend was waiting upstairs...
That was the day I learned that some guys just can´t handle guilt...

I recently had one of those awkward encounters, but for my ex, not for me. My ex had ended our relationship because he didn't want to commit at the time, but soon after we ended our thing he went back to his old girlfriend. I felt lied to and used, and I really wanted to tell him to stick it, but I something much better came my way.

I had the chance to meet the owners of a local sports team, and they invited me to sit in their private box for a game. My ex happens to work for the team, so I knew I would likely see him. I took the time that night to look great, etc. During the game, the owner's wife took me around and showed me the press box and we walked right past my Ex, who just stood there, jaw open, googly-eyed.

He and I are on better terms now, but that moment was priceless.

Ok, this guy was not an ex, so much as a one time date that did not go so well. He was a waiter at a restaurant by my house, and that is how we met. Well, we went on one date and he never called agin basically because I was not going to put out. Anyway, I stopped going to that restaurant for awhile, because I really did not wish to see him again. I started going there again after awhile, and he was never there, so I figured he quit. Well one morning I decided to go to breakfast with a friend and my boyfriend, and we chose that restaurant. Keep in mind I woke up, took maybe 5 minutes to get ready, and left. So we are seated, and the waiter walks over. And who is it but bad date guy? Suffice it to say it was a quiet breakfast with many pauses and he definitely recognized me.

Lol, well today during Biology, I had to be in a group with my ex boyfriend and his twin brother who is a pretty close acquaintance. It was soooo awkward because I haven't talked to him since summer, he dumped me through my friend cause he's a coward. Anyways, I could barely speak the whole time, and he kept saying really stupid things that made me even more embarrassed to know that I ever liked him, much less that I was DUMPED by him. hehe

My ex boyfriend is my neighbor so every few weeks I'm running into him. It's so awkward, we are not even on speaking terms. I saw him today outside of a window cleaning something and I'm sure he saw me. It's hard to keep cool at times, but it makes me cringe and think "OH GREAT" everytime I sense his presence. I'm past the crying devastation stage but it would be so much easier if I didn't run into him unexpectedly.

So lesson is never date your neighbor!!!!!! Especially in a foreign country lol.