Most Awkward Convo You've had...

Emmy1493

SO I like these type of threads, and I am curious. What is the most awkward conversation/situation you have been in before?

I'll start.

I was out running errands yesterday and went to a local beauty store. I look around and find what I need and proceed to the checkout. Here's the slightly awkward part. (Maybe I am thinking too much into this, oh well.)

The cashier is a really decent looking guy with long hair, and his make up was on point. So I though maybe he was trying to lean more towards the feminine side....? 

We get into a conversation about a product I bought and he then asked if I wanted my receipt in my bag, to which I replied "Yes Sir...." and then I felt bad. And it got quiet. Oopps  Should I have addressed him as ma'am? I never know how to address someone in this particular situation who had manly (his voice..kinda..), but more feminine features such as make up, etc. I complemented his makeup and started rambling like I always do when I feel awkward. So there's my tale.

 And I mean no offense what so ever to anyone in this situation. I believe my darn brain goofed. I knew someone who I used to be close with and I knew him before he went transgender, so I was so used to calling him a HE, and I could tell it bothered him/her. SO I guess that is my awkward story.

Anyone else have any stories maybe more awkward than mine?

Let's hear 'em!!

climbingsingle

Last weekend, at a party, I asked someone how married life was. And she said, "I'm getting divorced." I felt like a huge asshole. 

A few weeks ago, I was talking with the owner of my company. I had mentioned that my FI and I had tried hot yoga. And then he told me after he does hot yoga, he feels like he just had sex. Um. Gross. 

KatWAG

When someone asked me how far along I was, when I wasnt even pregnant (or trying) yet. That  got awkward fast.

Emmy1493

ClimbingBrideNY said:

Last weekend, at a party, I asked someone how married life was. And she said, "I'm getting divorced." I felt like a huge asshole. 

A few weeks ago, I was talking with the owner of my company. I had mentioned that my FI and I had tried hot yoga. And then he told me after he does hot yoga, he feels like he just had sex. Um. Gross. 

Bolded 1: Yikes! I have done something very similar to that. But heck, it happens lol.

Bolded 2: Oh, gross. Very very gross.

Emmy1493

KatWAG said:

When someone asked me how far along I was, when I wasnt even pregnant (or trying) yet. That  got awkward fast.

Oh gosh! That's why I never ask that unless I know 100% sure!

afox007

KatWAG said:

When someone asked me how far along I was, when I wasnt even pregnant (or trying) yet. That  got awkward fast.

I had this happen at FSS little league game. One of the players grandmas came over and was so excited and put her hand in my tummy. She was the sweetest little old lady and seemed so happy I couldn't bring myself to tell her I wasn't pregnant!

Another awkward moment was when FI and I first met my BFF's new boyfriend. BFF has slept with my FI and the 2 if us joke about it from time to time and apparently neither had a brain to mouth filter that day and mentioned it. As soon as the words left out mouths brunch got VERY quiet.

netskyblue2

My Ex MIL (she was just BF's mom at that time, I was 17 or so) kept trying to talk to me about the sex life she assumed I was having with her son.  I was a virgin.  I told her this.  She didn't believe me.  WTF?  She was drinking at the time, though, but I was SOOOOOOO offended.  (I was 100% goody two-shoes).

sarawifenow

I was at dinner with a high school boyfriend and his parents when the topic of baby names came up due to his older sister being pregnant. I went on and on about how I hated a particular name only to find out (very strictly) from his mother that the name I hated so much was her grandfather's name and a very large contender for the baby's name should it be a boy. I tend to not give opinions on names anymore!

jdluvr06

I told someone they had a really cute baby boy once... It was a girl. Now I just say you have a cute baby.

mysticl

I was on pain meds at the time so I didn't feel awkward at all but I'm sure I made a nurse feel like crap.

I was 17 and just had an appendectomy (as in it had happened in the last couple of hours).  My mom's boyfriend (now her husband) had come into my room to sit with us.  Up to that point the only visitor I had was my mom.  So the nurse comes in and says "Are you Dad?" to the boyfriend.  I said "no".  The nurse then says "Where's Dad?"  I'm sure she's thinking something about this poor, sick, kid who had to have the surgical team called back into work because she couldn't wait and her father can't be bothered to visit.  My answer was "dead".  She shut up real fast.  

Follow up awkward conversation was a couple of weeks later.  I obviously missed a fair amount of school due to my surgery (I also had a respiratory infection on top of it).  One day the school vice principal calls and asks to speak to my father (Mr. mylastname).  All of my student information forms stated that he was deceased (I know because we filled out our own forms each year).  My mom answered that one.  

The moral of the story……Always read the chart/file before you assume stuff.  

misscoffeeplease

The main line rang and I saw my co-worker's name on the caller ID. I thought my co-worker was calling the main line and he wasn't in the office. I usually just address him and say "Hello Mr. Co-Worker's Last Name..." and there was a pause for a moment and a woman's voice came on. 

She goes, "Actually, it's Mrs. Co-Worker's-last-name." D'ooooooh. She laughed though and I apologized profusely to his wife and called her by her first name. Totally awkward.  

mysticl

jdluvr06 said:

I told someone they had a really cute baby boy once... It was a girl. Now I just say you have a cute baby.

My son gets called a girl because he hasn't had his first haircut yet (he's 19 months).  I can have him dressed "boy" even to the point of his shirt saying something like "Mommy's little man" and people see the hair and assume.  

ElcaB

Once I was trapped in the car with my stepmom, who I don't really like (we've learned to get along, and she has her good moments, but she can be very strange and difficult to like). I was rambling about FI's and my decorating plans for our new apartment (we were moving in together for the first time). 

There was an awkward pause and then she started to tell me how wrong it is to live together before marriage & go into the premarital sex talk. 

She had me trapped & it was horrible. It was a very, very long drive. 

shaylagirl

My dear, sweet grandmother once called the guy I was currently dating by the previous boyfriend's name.

Current guy didn't know what to say.  Entire table fell silent.  Whoops!

Or, (then) FI's grandma (who's hard of hearing) telling me about how beautiful and wonderful (then) FI's wedding was to his ex-wife.  He told her to stop talking about it (I muttered so only DH could hear "Yeah, because THIS isn't awkward."), and she turned around and smiled, patted my hand and said "Awww, she doesn't mind!  You don't mind, do you dear?"

Uhm....*blink**blink* 

He apologized profusely to me later about it.  Wasn't his fault.

OHH!!! OHHHH!!!  Or, the evening before our wedding, Nanny left the dress she planned on wearing at her house 3+ hours away.  I ended up having to take her shopping in this hour and a half window before our kids had a band performance.

There is nothing, and I mean NOTHING like helping an 80+ year old woman get dressed (I mean, yes, get DRESSED!!  She was in her bra and panties [she uses a cane to walk]) and having her slap her breasts and go "GURL!!  This ain't gonna fit!!  I've got TITTAYS!!!"  Loudly.

I almost died laughing in the changing room.

And then, when we walked out and he asked her if it fit, she had to repeat "No!!  That won't work because of my tittays!!!!"

I love the crazy old woman though.  She makes me laugh.

grumbledore

Last week I called a doctor's office (during work) to return a call about one of our clients - I asked for the person who called me and said I was returning their call about the client's insurance information and the woman who answered said "Oh, ok, that's me" and then proceeded to start loudly shuffling paper.

I waited, assuming she was pulling his chart/finishing something she'd been in the middle of when the phone rang/other perfectly plausible explanation for the silence+paper shuffle.

This went on for about a minute, at which point I said, "Hello?"

She responded,"Yes, I'm here," and continued loudly shuffling paper.

At some point I put her on speaker so I wouldn't have to keep holding the receiver.

This went on for another 90 seconds, at which point I was about to scream and decided to just hang up and try again later.  I smack the phone back into it's base and mutter, "Fucking call me back!" in exasperation.

Well, on our phones, if you put a call on speaker, you have to hit the button twice to hang up.  So she heard me, said "I'm sorry, what?" and I hung up for real in a panic.

I immediately called back and pretended I'd been juggling three calls and accidentally hung up on her, then said, "I have that information whenever you're ready," and she said, "I'm ready when you are."

Apparently we'd both been sitting there in silence waiting for the other weirdo on the phone to say something.  It was the most ridiculous phone call of my life.

wandajune6

My awkward conversations as of late have come down to race. FI's family keeps commenting about how they hope our future kids have blue eyes like mine. They won't. Genetically, I'm about as recessive as you get. He's not. When we have kids, they'll look nothing like me.

I've also gotten comments from family and friends about redheaded babies. My niece is 2 and looks just like me so I get a lot of comments about having one that looks like her when it's my turn. Again, not gonna happen.

I either pause until the person backpedals or dismiss the comments. FI plays along with the comments. His son got very confused in biology class because of it!

grumbledore

My DD is a tiny little thing and has pretty blonde hair and blue eyes and I know when/if FI and I have kids they will likely be 100 feet tall with brown hair and brown eyes lol.  If we're lucky, they might get the red hair - I have it and his beard is red so...  But it's going to be mud brown eyes all the way.

MrsMack10612

shaylagirl said:

My dear, sweet grandmother once called the guy I was currently dating by the previous boyfriend's name.

Current guy didn't know what to say.  Entire table fell silent.  Whoops!

Or, (then) FI's grandma (who's hard of hearing) telling me about how beautiful and wonderful (then) FI's wedding was to his ex-wife.  He told her to stop talking about it (I muttered so only DH could hear "Yeah, because THIS isn't awkward."), and she turned around and smiled, patted my hand and said "Awww, she doesn't mind!  You don't mind, do you dear?"

Uhm....*blink**blink* 

He apologized profusely to me later about it.  Wasn't his fault.

OHH!!! OHHHH!!!  Or, the evening before our wedding, Nanny left the dress she planned on wearing at her house 3+ hours away.  I ended up having to take her shopping in this hour and a half window before our kids had a band performance.

There is nothing, and I mean NOTHING like helping an 80+ year old woman get dressed (I mean, yes, get DRESSED!!  She was in her bra and panties [she uses a cane to walk]) and having her slap her breasts and go "GURL!!  This ain't gonna fit!!  I've got TITTAYS!!!"  Loudly.

I almost died laughing in the changing room.

And then, when we walked out and he asked her if it fit, she had to repeat "No!!  That won't work because of my tittays!!!!"

I love the crazy old woman though.  She makes me laugh.

My mom did this to my brother's current wife.  It didn't go over well.  Unfortunately, between my brothers they've had 5 wives.  Mom was always a little flaky and it was still early in the marriage.

Jells2dot0

I've had this happen a few times, but one instance was DH was trying to find a new renter for his home. So, me, DH, and DH's daughter went with him to meet a potential candidate. The guy, who was a sweet, older man, saw SD and me and said "oh, you have such beautiful daughters!" SD and I busted out laughing, which was rude, but I couldn't help it. My DH just said "Oh, this (pointing to me) is my girlfriend, but thank you!"

CMGragain

I taught school for many years..  Once you have done that, you are immune to embarrassing conversations.
The past five years, I substituted in schools when I was feeling well enough.  When I was in chemo for breast cancer, I wore a wig.
One freshman high school boy was obviously hyperactive (ADHD) and not on meds.  (My own son is ADD, so I can spot it easily.)  He kept up a constant chatter. None of the other students paid any attention to him.  Finally he focused on my hair.  "Is that a wig?  I bet it"s a wig!  Why are you wearing a wig?"  After several minutes of this, I pulled off my wig, exposing my bald head, and said "I have cancer."  There was a huge intake of air, as the entire class froze in horror.
"Now," I addressed the young man, "do you think that was a proper question to ask your substitute teacher?"  "No," he whimpered.  "I'm really sorry."
I asked if anybody else had any  questions.  One girl asked, "Is it true that if you get breast cancer, they cut off your breast?"  "Yes, " I replied, "and you don't get to ask which one."
There was a girl in the front row who was convulsed with laughter and trying to hide it.  She was the daughter of my oncologist, and thought I had balls!  The whole school heard about it by the time I left for home.

larrygaga

Some guy was hitting on me at a bar, and asked me how old I was. I told him 23, and he was like Yikes I thought you were 15!!! Then he walked away and didn't bother me for the rest of the night.

WHAT

FI's aunt always asked me how much weight I lost. She always guesses around 30lbs everytime I see her. I'm pretty in shape and I haven't lost any significant weight since we've met. I think she just assumes I'm huge. 

chibiyui

larrygaga said:

Some guy was hitting on me at a bar, and asked me how old I was. I told him 23, and he was like Yikes I thought you were 15!!! Then he walked away and didn't bother me for the rest of the night.

WHAT

FI's aunt always asked me how much weight I lost. She always guesses around 30lbs everytime I see her. I'm pretty in shape and I haven't lost any significant weight since we've met. I think she just assumes I'm huge. 

To the first part.

WUT.

I've gotten the assumed pregnancy comments before. My mom the last time we were out randomly put her hand on my stomach and said it looked like a baby bump.

I need to wear my corset at all times apparantly.

LadyMillil

My research is on sexually transmitted infections in the female reproductive tract. I get to sit around my all male lab and talk about the biology of the vagina with them, which always leads to awkward conversations. Usually I say things like "I got herpes in the mail today" or "I'm off to lavage (wash) vaginas".

jenna8984

I accidentally wished my very Jewish friend a Merry Christmas. 

My ob/gyn was the sweetest old man just before he retired. But the casual conversation mid exam was always so awkward. Can we not talk about your grandchildren while your hand is inside me, thanks. 

Couggal12

Actually I have an OB/GYN story. Was awkward at the time for at least me. When I was 21 I had just broken up with my exbf and was due for my yearly exam. I figured I should probably get tested for everything & and I also wanted to get new BC. Anyway I explained to her that I had just gotten out of a 3 year relationship but, figured it was a good idea to get everything checked out. She paused for a second and then asked if it would be okay if an intern came in. They hadn't gotten to do a yearly exam yet, and tests for STDs and this would be good experience. So I was like sure whatever. Well, in walks a young, hot looking intern and then I had to answer a million sex related questions. She kept coaching him through like "She seems to low risk but, we should check for this too".  I know he was an intern but still, didn't want a McDreamy looking at my lady parts back then.

Guess the good part was everything was all good!

 

 

smalfrie19

FI and I were out for dinner one night right after Father's day and the waitress asked if we were celebrating that and we looked confused and were like "no??" and it didn't hit us til she walked away that she thought he was my dad....mm...awkward. 

APDSS22

At camp once near the pool the director of the camp walked up to one of the moms from the "Mommy and Me" camp for 1st/2nd/3rd graders and their moms we had that week.  The mom had a slightly bulging tummy and wet spots over the breasts on her swimsuit and the director asks her "oh! are you nursing?".  Woman looks totally confused and offended, apparently her swimsuit just hadn't finished drying since she got out of the pool.  That taught a very young me that it is never okay to assume someone is or isn't pregnant.

JCbride2015

SaraBrideSoon said:

I was at dinner with a high school boyfriend and his parents when the topic of baby names came up due to his older sister being pregnant. I went on and on about how I hated a particular name only to find out (very strictly) from his mother that the name I hated so much was her grandfather's name and a very large contender for the baby's name should it be a boy. I tend to not give opinions on names anymore!

OMgosh, awkward name stories are the worst.  Sometime the summer after high school, I was at a BBQ with SM's family.  We were discussing people with weird names and here is the story I was trying to tell: "There was a girl at my high school named Susan... but she wouldn't let anybody call her Sue.  She was super proper and it was weird to call a 15 yo Susan."

Well I got to the first word "Susan" when SM's young guy cousin burst out laughing and was like, "I don't want to stick around for how this ends."  Of course I wasn't thinking that SM's sister's name is Susan, and without the ending of that story, it sounded like I just hate the name.  So I awkwardly finished the story but by that point I was probably beet red and totally embarrassed.

Here's another one, although not mine.  One of my teacher friends saw "Abcde" printed on her course roster.  She said to the class something like, "Looks like I have a typo.  It says A-B-C-D-E [Lastname].  What's your correct first name?"  A kid raises his hand and says, "That's my name.  It's Abcde."

Pronounced Ab-sah-dee.  D'oh.

bride2b71614

I have always been a biology enthusiast. During my junior year in college, my FI decided that it would be a great idea to get me a biology related gift for valentines day. On valentines day he came up to me and my friends in the quad and says, hey babe, guess what I got you for valentines day? I guessed flowers, chocolates, a teddy bear? He smiles really big and goes, no I gave you herpes and mono loud enough for my friends to hear. They were all in shock and started yelling at him. I FREAKED out and went off on him for a good five minutes, he was laughing the entire time. Well, long story short, my FI got me mini-plush herpes and mono microbes. Unfortunately, my friends misinterpreted the entire exchange and thought I had herpes and mono because of him. I literally had to show them the plush microbes so that they understood that no, I didn't have herpes or mono, and that no,this was not real and that he's not a scum bag. While this was all done in good fun, it was terribly awkward. 

[Deleted User]

jdluvr06 said:

I told someone they had a really cute baby boy once... It was a girl. Now I just say you have a cute baby.

I have totally done this too! I feel like it's worse to ask if it's a boy or girl so I do what you do- just leave at cute baby...

themuffinman16

 Being put under makes you say the darndest things. Thank God you rarely see anesthesiologists, again.  I once went in for a D and C for endometriosis.  The black anesthesiologist took my arm and inserted a line, he then told me I can have my arm back because my boyfriend might get mad.  I said... "Yeah, he would.... because, you know... once you go black you never go back.  Have you ever heard that?  Once you go black you never go back?"  When I came to I remembered what I said and the anesthesiologist was checking up on me.  I never blushed so hard in my life.  I said I was sorry.  He said for what?  he must hear that stuff from loopy patients all of the time.  How humiliating!

The first time I had to have a D and C and a biopsy (endometriosis is a bitch) I was being wheeled into the OR for surgery.  They switched me to a different gurney and I felt the floor drop away from me.  I screamed... "WHERE DID THE FLOOR GO?!!!"  The doctor said, "Looks like the anesthesia is working."  I said, "What I don't remember the gas mask over my face."  The doctor said that he inserted it intravenously into my line.  I blurted out, "SNEAKY BASTARDS!!!!"  And that was all I remembered. Lol