Okay, top this awkward situation

[Rylot]

So yesterday I volunteered to do some face painting at a pretty major event in South Austin (Eeyore's Birthday). It was an outdoor sort of state fair sort of thing with an odd mix of families and hippies. Most of the people being painted were younger kids wanting rainbows and T-Rexs however a few women did come in and get 'body art' (boobs painted) from time to time. I have no idea why it was legal to walk around half naked but no smoking laws were still in effect; but anyway, so while I was painting the eighth unicorn a gal sat down at the station next to mine and proceeded to remove her top and she had some pretty nice breasts.

Now it's worth mentioning that my girlfriend was working the same booth with maybe twenty or so other volunteers and fifteen or so painting stations. But I wasn't going to just sit there and start drooling and she knows I'm not the cheating type so she didn't really care and I just went about trying to paint a Spider-man face on a squirming three year old number seven. However the situation reached sitcom levels of contrived awkwardness when my mother-in-law came over to my station. The sheer amount of concentration it took to keep my eyes on the Dachshunds I was painting on my mother-in-law while not sneaking a peek at the flower bosom not more than five feet away was damn near Herculean. The best part was the my Mother-in-Law knew exactly what was going on so she was teasing me the whole time. Definitely the most awkward situation I've been in.

 

[Leadfinger]

All I can say is, that sounds pretty awkward. Really, anything that involves a mother-in-law and boobies is going to be quite awkward.

 

[manic_depressive13]

How can she be your mother-in-law if your girlfriend is your girlfriend and not your wife. Also that situation is only really awkward if you had a boner.

 

[Elementary - Dear Watson]

How can she be your mother-in-law if your girlfriend is your girlfriend and not your wife. Also that situation is only really awkward if you had a boner.

And if the boner was touching the mother-in-law... and the girlfriend cheated with the wife...

 

[Clowndoe]

I'm not sure if this is perfectly within the theme of the thread but I got something involving inappropriateness and mothers and whatnot.

This one time me and and a friend of mine were sitting down at the ice cream place. Standing in line near us was a mother and her daughter I assume, and she was about 12-13 years old, so as a joke I told him in a none-to-subtle voice "Hey, quit eye-banging 12-year-olds." I don't know if the girl noticed but the mother seemed visibly distressed and we both knew it, so, unperturbed, he coolly replies: "Yeah, you're right. Too old." Nervous side-glances were had all round Wild Willies that day.

 

[krazykidd]

About a year ago i was working retail . I worked with my mother-in-law ( she became my mother in law after we started working together . ). We were walking towards each other , apparently she was daydreaming and walked into a wall . This knocked her off balance and she was going to fall . Trying to regain he balance in that split second she grabbed the first thing within reach of her hands , which just happened to be my balls. When you are falling , and grip something , you grip it pretty hard . She litterally pulled herself up while holding my balls . This was painful and halarious . I started to laugh and she got all red and walked away . With aching balls i texted my girlfriend and said : "Your mom just grabbed my balls ". I didn't offer an explination nor context to my girlfriend . When i got home she was so mad , because she thought her mom was trying hit on me .

 

[Auron225]

Walked in on my friends mum naked once. I was about 12 or 13 at the time. What an awkward day that was.

Aside from that, I was with a friend and a bunch of random people who I'd just met and was still learning the names of. I was told them all in rapid succession and seemed to have chosen that very moment to not pay much attention. Anyway, we were talking about people names we thought were stupid and I decide to chime in with "I don't understand why you would choose to call your child Ruth of all things. It just doesn't sound nice at all". Dead silence - you could hear a pin drop. That was when I realized one of the people in the group was called Ruth. Haven't see any of them since - it's probably for the best! Looking back I do find it funny but I'd never want to repeat it!

 

[Ti0k0]

When I was 13 orso I walked in on my dad eating my mom out at 07:00 AM... Hey dad, I missed my bu....

 

[Vigormortis]

Top that? Okay, sure thing. My life's been full of incredibly awkward moments for as far back as I can remember. Guess I'm (un)lucky that way.

One of the more recent occurred during a going away party for some friends.

Needless to say, copious amount of alcohol were present, being this would likely be the last time any of us would see these friends for quite some time. At one point, after God knows how many shots and mixed drinks had be consumed, one of the party goers (a very close friend of mine) pulled me aside to chat privately. Without going too much into details, she confessed to me that she'd been cheating on her husband (another friend of mine) for at least five years. She laid out all the sordid details and regrets, etc, etc. I didn't say much, since I had no idea what to really say at the time. Plus, I'd had my fair share of the "spirits", so my brain wasn't entirely clear.

After about ten minutes of awkward, private conversation, we walked our separate ways back into the party crowd. Moments later, another close friend of mine (her husband) approached me, clearly more than a little tipsy, and drooped his arm around my shoulders, looking to start a friendly conversation. (we hadn't talked in weeks) However, after the standard jovial friendly greetings, but before chatting proper, he said, "Man, you and 'name-redacted' were chatting for some time over there. What were you two talkin' 'bout? Planning a crazy weekend of raunchy sex or something?"

At which he laughed. And I tried laughing along with him, if only to cover the incredible awkwardness I was feeling.

That party was all kinds of distressing...

 

[Zen Bard]

Could have been worse...

Your "mother-in-law" (I'm assuming this is your girlfriend's mother. So kudos on your forward thinking!) could have sat down, taken off her top and asked you to decorate HER decolletage!

Keep Austin Weird, fellow Texan (I'm a Dallas-dweller, but don't hold that against me)!

 

[Bestival]

Once when I was 15 or so I ate dinner at a friend. Later that night when I got home, I smelled that my parents had had shoarma for dinner. So without thinking I commented to my dad; "Oh, you guys ate sperm?". The words sound pretty similar in dutch, but nowhere near similar enough that my dad didn't notice.
He even corrected me.
It was pretty horrific.

 

[Xan Krieger]

Was at a friend's house and he asked if I wanted to watch a movie. I said sure so he put a movie in the VCR without showing me what it was. A few seconds later on the TV appeared his parents having sex. I haven't looked at porn since.

 

[Bug MuIdoon]

Snip'eth

You should have flipped it and played your mother-in-law at her own game by staring at her boobs.

 

[Happiness Assassin]

Was at a friend's house and he asked if I wanted to watch a movie. I said sure so he put a movie in the VCR without showing me what it was. A few seconds later on the TV appeared his parents having sex. I haven't looked at porn since.

Ding ding ding! We have a winner. I was going to post something about having my parents go through my search history, but... damn.

Beyond that, nothing really awkward for me. I am pretty good at avoiding those kinds of situations.

 

[Something Amyss]

How can she be your mother-in-law if your girlfriend is your girlfriend and not your wife.

That's how his girlfriend knew he wasn't the cheating type: she knew his wife would kill him and her mother would tell her.

 

[MysticSlayer]

One time my mom ended up giving one of those "I'm too good for you" looks. You know what I mean: chest out, head up, looking down the nose. I knew she did it unintentionally, but I couldn't help making the snarky comment, "Haughty." However, given the context and the fact that she didn't have any spelling to let her know it was "haughty" and not "hotty", she thought that I was hitting on her. My brother also took it that way, but they never explained their shock and anger adequately so I was busy going "What's the problem?" Thankfully, my dad understood what I meant and cleared things up, but it was still awkward none-the-less.

My really religious mom also one time used a camera that caught me masturbating (wasn't her intention, it just happened that it caught me). Yeah...nothing like trying to come up with an excuse for what I was doing in that situation (it wasn't 100% clear what I was doing). Eventually I confessed, but that didn't make the situation any better, especially after she said, "If you do that again make sure to tell me!" After a brief pause she clarified by quoting some scripture about confessing sins.

Believe it or not, even after those two instances, I was still considered "the good little angel" of the family.

 

[New Troll]

Way back when, while my ex-wife and I were young and just started dating, we were watching a boring movie in my bedroom when I decided to go down on her. While pleasuring her nether-regions, all of a sudden I hear my mom's voice asking if we wanted her to warm up any left-over pizza for us. I quickly told her no thanks and looked up to see her shutting my bedroom door. It was dark in the room except for the TV shining, so I asked my girlfriend if she thought my mom could see what was going on. She told me she never noticed anything. Took that as a compliment, but still... never had the nerve to bring it up with my parents.

 

[bluerocker]

Playing against this [http://www.youtube.com/watch?v=OPnxf_HOydM] boss when my roommate walks in.

Spoiler warning for anyone playing Persona 4!

Now for those who don't care about the youtube video: Out of context, you're essentially fighting an evil stripper on a pole, complete with humping of the pole, squishing noises and moans. Yeah, that sucked when the Roomie walked in.

 

[KelDG]

Why are boobs in public such a big deal in the US?

On Topic - When I was younger I went round to an old GFs house one afternoon, not realising her bed makes quite the noise downstairs "insert Mr Bean meme here". Later in the evening we came downstairs for some food and I got, to put it mildly a dissaproving look off her mum and a couple of knowing raised eyebrow looks from her dad. Queue an awkward dinner with the GFs family...... GF was mortified, the mother could have killed with her eyes, luckily her dad liked me enough to see the funny side of the situation..... LUCKILY :/

 

[Cabisco]

Many of these are hilarious, gold stars for sharing everyone!

The most awkward moment I can think of is when after a long heavy night of partying at our house after we had come back from a club where it hits about 4.30am and everyone starts to either go home or back to there various bedrooms or sleep whereever they can find. Anyway I was laid in bed and my mate silently opens my door and whispers if i'm awake, I am so he proceeds to tell me to come out into the hallway. I do and I suddenly notice a quiet sound, my friend tells me our other friend is shagging a some horrible girl we know in the next room, we peer through the half open door and confirm this without being noticed. The problem is the guys girlfriend has come over for the weekend and is currently wandering around the house looking for him. She actually appeared at that moment and asked us if we had seem him, we just didn't have the heart to say 'yeah he's just through that door cheating on you'. So awkward... If she was angled slightly differently she would have seen it all.

I just don't understand it, why cheat on your lovely kind hot girlfriend with a very annoying swamp monster when she's in the same actual house as you.

So yeah, that was pretty awkward.