The 5 Most Awkward Things I’ve Said In Bed (That Still Got Me Laid NSFW)

As a full-blooded, completely self-aware awkward person (I have a bad habit of giving high fives at the end of dates), I am prone to saying a lot of stupid shit. As a single young woman, this has on occasion jeopardized my interactions with potential new friends and/or partners. However, as a sexually active individual, this has also led to some very awkward, retrospectively hilarious circumstances in bed—luckily for me, my partners’ libidos seemed to always win out, and I managed to escape each one without killing any boners. Here are some of the most awkward, cringe-worthy things I’ve said in bed.

1. “Hey there, little guy!”

We had been dating for about a year and fucking for a little less than that. His penis isn’t actually small (overall pretty average, I’d say) – I was just feeling whimsical and decided to greet it accordingly, “Hey there, little guy!” He was more confused than offended, thankfully, and he never did get used to my weird sense of humor.

2. “Are you going to take them off, or are you waiting for my shorts to soak through?”

It was winter vacation, and we were both back home from college. We had been in a lot of classes together in high school and had kept in touch with promises to meet up. After hanging out at the hookah lounge, we drove in his Mustang to the beach and started making out. Then we started taking off each other’s clothes—except for some reason, he left my shorts and panties on. After a while of being hot and bothered, I asked him, “Are you going to take them off, or are you waiting for my shorts to soak through?” He laughed a little sheepishly. My shorts eventually came off. (Okay, so this one technically did not happen in bed, but we did hook up, so there was a metaphorical “bedding”.)

3. “Wow, that’s crooked!”

It was the first time I was hooking up with my soon-to-be friend-with-benefits. He was the drunkest person at the party; and I, the second drunkest. We knew each other through a mutual friend and thus embarked on a wondrous sexual adventure together. As we sloppily kissed each other and threw off our clothes, I was briefly taken aback when he dropped his shorts.

There wasn’t anything particularly unusual about his man parts; it just didn’t quite hang straight (though, at that point, it wasn’t doing very much hanging). Of course, in my drunken, oversharing stupor, that seemed like the appropriate thing to comment on: “Wow, that’s crooked!” He paused and looked down. “It’s not that crooked,” he slowly responded, clearly on the defensive. I assured him that it was merely an observation, not a criticism, and we carried on. The angle actually felt fantastic.

4. “You’re such a white boy.”

Valentine’s Day arrived, and I was single. I had been texting a guy I met a month earlier, and we intended to meet up that night for a concert to which he won tickets. It was also my friend’s twenty-first birthday, so by the time I reached the concert venue (he lived in another city), I was happily hammered. At his place, we quickly shed our clothes and went at it, having mutually looked forward to this moment for weeks.

After a good amount of making out in his bed, I rolled on top and, grinning at him like an idiot, blurted, “You’re such a white boy.” (For context, I’m Asian.) His brows furrowed, and he asked me if I had been with other white guys before. Not knowing how to answer (partly because it was a weird question, but mostly due to my mortification at what had come out of my mouth), I went with the truth—he was not my first white boy. He was apparently satisfied with my answer because he proceeded with some of the most glorious sex of my life.

5. “Sorry, my bones are creaky. I’m an old woman.”


My joints crack a lot. It’s probably a medical condition that I haven’t gotten checked out, but it hasn’t physically impeded me in any way. Yet. Sometimes my jaw cracks when I’m kissing another person. My shoulders crack if a stretch my arms upwards. It isn’t painful; it just happens.

I had just woken up the morning after going home with an extremely attractive semi-stranger (Acquaintance? Almost friend?), who had fallen asleep beside me with the promise of a second round in the morning. Of course, without liquor clouding everything but our libidos, the sober morning sex had a few additions to the menu—namely, the symphony my bones performed as we bumped uglies. Grimacing at a particularly loud crack from my elbow, I tried to joke, “Sorry, my bones are creaky. I’m an old woman.” Which was an awful joke because (a) he was clearly older than me, and (b) that is one of the least sexy things to say mid-coitus. Thankfully, I think he found my awkward humor endearing, because he smiled slightly and carried on with our morning romp.