World's most awkward conversationsFollow

I was thinking about it today, as I was going into a session, where I had to address some financial issues with a client. Talking about bounced checks and accumulated fees is always an uncomfortable but necessary interaction. And I thought about other awkward conversations.

I'd say hands down, the most awkward conversations were coming out to my family. I was 18 when I came out to my siblings and 19 with my mother. It was 1989 and 1990 respectively and I had relatively few templates to go on. Knowing my mom and my siblings, I'd figure that they'd take it well, which they did. They handled it better than I did. My mom said that she and my sister had wondered to each other about it before but still, it was SO awkward. Maybe partly b/c I was uncomfortable talking about something vaguely related to sex--and at that time, with the way that the closet seemed to be--there was something sexually tinged about it. I dunno. It's like if I was straight I could talk about boyfriends and the public life whereas I had to reveal my secret desire for girls.

Not traumatizing but awkward. And I was thinking, what other types of awkward conversations are there?

Edited, Jan 12th 2010 9:16pm by Annabella

"No, Aunt Donna, you really don't want to know what website your teenage son got the virus from. And by the way I'm never fixing any of your computers again"

But I loved that toaster! Breakfast has never been the same! The bagels just aren't as crispy! I'll never get over it! NEVER!!!!!!!!!!!!!!!!!!!

Telling my parents that my girlfriend was pregnant was bad enough, but it just got worse when my dad asked if it was mine.

Considering nothing came from it, I'm assuming the dumb cunt was lying to me about either or both points.

Four in the morning. I was tired and my feet were killing me. So I heft my duffel bag packed with my clothes over my shoulder from my car and head into my parent's house (whom I had been staying with), figuring everyone was asleep. Which was good. Because the night was spent at a really, really upscale LBGT club and I was dressed to the nines like a goth Catholic schoolgirl. And yes, it was hot.

Little did I know not only were people NOT asleep, they were hanging out in the kitchen, my only access into the house. With friends. Smoking weed. So, I open the door and sort of stand there, hand on one hip, the other struggling to hold the duffel bag against my tiny frame and get about half a dozen odd stares.

For a full two minutes. Parents chilling out and smoking pot. Their twenty-one year old son dressed like something out of Heavy Metal magazine. One kitchen. It took one of their friends to speak up.

"We won't ask any questions if you don't."

If they were asked, for the record, none of that ever happened. Ha ha. Denial.

I got to describe, in graphic detail, to my boss & HR manager over speakerphone, immediately after being woken up (Work nights, sleep days), how I saw one of our employees receive a BJ in a car in front of the hotel a couple nights ago.

Luckily, the HR manager himself started cracking up the first time, so it was easier after that happened.

Maybe he liked you?

Conversations with my father in law where he starts on a rant about "low class people" ruining South Carolina. He means "Black people", and he knows we know he means it. One of these days I'm going to lose my self-control and say something that will cause my husband to be written out of the will.

Hmm. My most awkward conversation would probably be a three way tie.

There was the time, when I was twelve, that my dad told me that if my mother divorced him, he never wanted to see either me or my brother again. Oh, and that we should take the dog, or he'd shoot him in the backyard.

Then there was the time, about three years later, when I saw him for the first time after the divorce. My brother and I had been in a car accident, and I guess he felt all fatherly so he invited us over. He told us, in great detail, how my mother had tried to leave him when my brother was only two years old, and that he admitted himself to a mental institution to get her to take him back.

And then there was the conversation, not too many years ago, when my father, who was now "back in my life" and wanted to be good friends, confided to me over the phone while he was drunk that he was still completely in love with my mother. To this day, I hope his current wife was working late that night.

Huh. I never got any warnings from work when they block sites...

I don;'t know that I've really had any awkward conversations, unlessit was work related and involved an under performing employee whose department head had failed to properly inform said employee of their underperformance. Some people really are too stunned to know they suck.

For anytrhing else, I've always held the policy never bring up a subject with me that youre not prepared to hear an opposing view on, and as a result, have always felt the same way about anything I bring up.

I'm sure I had some awkward conversations growing up, but I don't really remember any of those either because they weren't that bad or I've subliminally omitted them.

Using naughty slang at work only to have a foreign colleague ask "what does that mean?" and everyone else back away leaving you to explain ...

My brother got married last year. Everything was cool, we were expecting this for some time. They told us it's going to be very classical wedding in a small church...

-Wait up, bro. Aren't you atheist?
-Yup.

Then he asked me for a favour. He wanted ME to go on HIS pre-wedding confession. No, it's not the awkward part. I agreed. Don't hate me, he made his best Cockerspaniel eyes. I figured I'd confess for myself and get signature for him. There are very few things I wouldn't do for him. Here it goes:

-Son, what's your fiancee name?
-Annie.
-Well son, be honest with me here. Are you and Annie living in a sin?
-Uhrmmm...