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After we had been together about 10 months, my now-husband moved to another state. I went with him and his parents to help with the moving process. My husband and his father went out shopping while his mother and I stayed behind to start unpacking stuff, right? We're chatting away, and she's just kind of roaming around the room while we talk, and then I look down and see that I'm sitting in a sea of condoms. Lo and behold, I'd accidentally opened up a box full of them while unpacking and hadn't realized it. I threw a t-shirt or something over them and scooped them up as quickly as possible while his mother's back was turned. Luckily, my now mother-in-law was too polite to say anything about it, then or ever. :)
DB_BROWN.jpg (8.8 KB, 24 downloads) 1 year old 
Well, it has nothing to do with my fiancee, but I remember my dad once tried to have a talk with me about drugs - telling me not to do them, obviously. Part of his lecture was to let me know that he used to "smoke grass". I was a teenager at the time, and thought this word, especially coming from my dad, was so hilarious, I couldn't stop laughing.
Ohhhh..yikes....last year my FMIL and FSIL were visiting at our house one night, and FMIL proceeds to tell us that one of her granddaughters (my guy's niece who is 15) asked FMIL to talk to her (niece's) mom about letting her go on BC. My guy had a mini-freakout, he was like I DON'T want to even think about my little niece needing BC...sigh....I love my FMIL (99% of the time anyways..)but sometimes she tends to overshare when there are folks around who'd rather not hear the details.
Yikes! Nothing involving my fiance and I yet. But about a year or so ago when I was living at my dad's, I went in his bedroom for some penny wrappers because I knew he kept change and coin wrappers on his dresser. Well, I found ANOTHER kind of wrappers on his dresser. And another time I found some enhancement pills for older gentlemen if you catch my drift. Eeewwww! Luckily, my dad and I have a don't ask, don't tell kind of relationship when it comes to sex. He doesn't want to know what my fiance and I do and I don't want to know what he and his girlfriend do.
And I don't ever go in his bedroom anymore!
My friends and I all got our tongues pierced in college, just for the hell of it. A few months later I went home for the first time to meet my boyfriend (at the time)'s parents. We were all out at a bar drinking and having a good time and his mom noticed the tongue piercing and started asking me all kinds of questions about it, including how to use it in sexual situations! I was not only horrified, but I couldn't stop laughing b/c she was so cute and funny and seriously considering getting one!
I have one about me. I started dating this guy when I was 19, he lived about an hour away from me and we both lived with our parents so it was hard to spend time together. Finally he just had me stay the night at his parents house, figuring they were never there anyway. The next morning I woke up and really had to go to the bathroom but the guy was no where to be seen. So I'm sitting there debating, should I stay,or should I go (now). (Great now that song is stuck in my head!) Anyway, I peek my head out and the coast looks clear, so I creep to the bathroom in my PJ's with bedhead. In the living room there sits his mom and his sister. I smile stupidly and scampered into the bathroom where I proceeded to bang my head into my hands. I then had to repeat said walk of shame to get back to the bedroom...ugh! Horrible, but funny to me now!
So SO's mother has a wicked sense of humor (I love the woman, she is hilarious!)
His Mom and Dad were out of town for the weekend, and SO talked me into sleeping over. His house has four bedrooms, and we slept in the basement one the first night. The second night, he was complaing about how uncomfortable the bed was, so he said we should move upstairs. I said ok, but none of the bedrooms upstairs belonged to guests- they were all a family member's. And trust me, this feels so wrong, and so tacky, and so terrible to me, but he suggested we stay in his parent's room (which was more reasonable than his little sister's or his older brother's). Against my better judgement, I agreed, but told him no hanky panky. So we didn't. The next day his parent's came back- I was in the pc room with the boy and his brother, when his sister (7 at the time) wandered in and tugged on my shirt, looked up at me and said "Mommy says Daddy told her the bed smells like you" I think my jaw dropped like eight feet, I was HORRIFIED, mortified!!! Come to find out FMIL told her daughter to say it to freak me out- and it worked, oh so well, lol, and FMIL got a jolly good laugh 
Worse though- we made the terrible mistake of buying a Liberator Zeppelin black label, the biggest one they make- SO said oh come on it will fit in our house, and I said oh no, it sure as hell will not. But SO got it in the mail (one box with the cover, and EIGHT seperate boxes of 45lbs each of foam (2 per box), I won't even go there, you have to fill the things yourself, it's hell, hah) and we assembled it. We did it in our very spacious hallway. And shortly after, discovered it would remain in the hallway for the next 5 months, lodged in there, because it got SO BIG, we couldn't get it through the door into the room were going to put it in 
Compare it to trying to shove an elephant into a Prius. So I had to make excuses to people, including my parents, as to why they couldn't come into our house for 5 months. In the end, we had to rip it open, fill 30 garbage bags with foam, and haul it all to the dump, where we received way too many weird looks whilst disposing of it. NEVER again!!!!!!
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So, last night FI called for our nightly chat and we were having a long talk about my health problem. (Got some "plumbing" problems, I've posted on it a couple times before.) Anyway, he had talked to his mom earlier in the evening and he said it was the most uncomfortable conversation he's ever had. She was inquiring about our, uh hem, bedroom hokey pokey life. Ranging from our practices to our hygine. I guess she even asked him how vigorous he was. (My reaction was like, NOOOOOO, soo uncomfortable, MUHAHAHAHAHAHAAHA, that's so funny) I laughed for probably 15 minutes straight because I can't even imagine his cute little mom asking something like that. It really lightened my mood about the whole health issues for a minute.
Anyway, my question, anyone else have some uncomfotable, yet lighthearted conversations or situations you've been in?