WARNING: This post may make you laugh so hard you’ll spew whatever beverage you are currently drinking.
Now that you’ve been properly warned, please continue on with this guest post from Rae Carson, author of The Girl of Fire and Thorns. Want to win a signed copy of the sequel, The Crown of Embers? Share your most awkward date story in the comments to enter!
RAE CARSON’S MOST AWKWARD DATE EVER
Once upon a time, I had a very bad crush. The object of my crush was a gorgeous guy with swarthy skin, thick black hair, dreamy brown eyes, and an amazing British accent.
We hung out a lot. Like, a LOT, which was as fabulous as it was frustrating. We always had a great time—we explored new restaurants, had long, deep talks, laughed easily together—but I worried that we would never get past the “friend barrier.” So you can imagine how ecstatic and a-fluttery I was when he finally asked me out on a real date. For two days straight, I walked around with an idiotic grin on my face, just in anticipation of the weekend.
He took me to San Francisco. We spent the whole day walking around holding hands, pretending to take in all the sights as if we were not wholly and utterly aware only of each other.
That evening, we stood on a knoll overlooking the Golden Gate Bridge and the sparkling San Francisco Bay. As the sun edged into the Pacific, he said, “Rae, there’s something I have to tell you.”
I gazed into his dreamy eyes, my heart pounding, thinking this is it. He’s going to say IT.
He regarded me longingly and whispered, “I have four nipples.”
I said, “Blug dhid ju juth thay?!” because, apparently, this is how I sound when someone is kissing me passionately after having just confessed to a cornucopia of nipplage.
I spoke to his chest for the rest of the evening, like this:
Him: Where do you want to have dinner?
Me, to his chest: Uh…somewhere in Little Italy.
Despite our inauspicious beginning, we ended up dating for several months. Turns out his extra nipples were not that interesting or remarkable—more like freckles, really. (Yes, I was disappointed.) But I’ll never forget that first, awkward date. It also explains why, when I met the guy who would eventually become my husband, I asked him outright, “How many nipples do you have? …Oh, no reason. Just checking.”
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Tell me about your most awkward date in the comments for a chance to win a signed copy of The Crown of Embers!
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LOL!
I haven’t had an awkward date, but I don’t think anyone can top Rae! You really had me rolling on the floor laughing!!!!
I LOVE the Picard picture it’s perfect! Anyways, my awkward date story:
It was the second date with this guy whom I had liked for ages. He was super sweet, we had a picnic lunch by the river, and it was Canada Day so we went to see the fireworks at night. We were going through the whole awkward should we shouldn’t we hold hands thing (real mature I know >.<).
So after the fireworks had ended and we were exiting with the masses we finally closed the hand holding gap and inwardly I was screaming YES!! Now night time in the summer where I live is probably THE WORST time of the year because mosquitoes will eat you alive. While we were walking in the dark one mosquito just so happened to land and bite me right in the eyelid.
At first I thought I had swatted it away in time, but then the tell-tale itching sensation began and before I knew it my eye had swollen up and swollen shut (if you’ve seen the movie Hitch with Will Smith and when he has a seafood reaction – my eye looked like his at that moment).
I tried to be cool and my date was trying to prolong our evening together a bit and asked if I had wanted to go for coffee. At this point tears were streaming, I was trying not to itch and I kind of got irritated and short and told him I just wanted to go home. He totally thought I was brushing him off and it got quiet and awkward, but I didn’t want to tell him what happened (I’m stupid I know).
I explained what happened the next day to him and he was just so relieved because he thought he had blown it somewhere along the line. But we still laugh about it to this day (5 years later).
This isn’t quite as funny as yours.
My friend and I went on a casual double date with another couple of friends, while we were all in college. They were your typical poor college student guys. We ended up picnicing at the top of this hill overlooking the ocean in Santa Barbara. It was a beautiful day. They had packed us dinner. So I’m thinking, wow, these guys made dinner! Well, they had "packed" dinner, not "made" dinner. They’d brought hand-packed tupperware of mashed potatoes, cole slaw, and fried chicken. My friend was like, "Wow, this looks great. You guys did such a great job!" I looked at the guys and smiled to myself. It was totally Kentucky Fried Chicken, but I didn’t have the heart to call them on it or embarass my friend.
A month later I started dating steadily one of the guys (who is now my husband). I asked him about the whole KFC thing and we laughed. Turns out they hadn’t intended it on looking like they’d cooked dinner, they just wanted to pack nicer containers. But when my friend acted like they’d cooked it, they didn’t want to embarass her for not recognizing KFC.
Crown of Embers! SQUEE!!
Okay, sorry about that. I’m back now.
Most awkward date ever?
I had a crush on a guy I worked with, who seemed completely oblivious to my interest in him. We talked often and got along well, but he didn’t seem to catch on to my interest in him for months.
When he finally asked me out on a date, we had a nice but completely unmemorable time. I have no idea where we went or what we did. I just remember he was funny and kind and I felt like all of the sudden, I had no idea what to say to him anymore.
At the end of the date, he leaned in for The Big Kiss. I’d been waiting for it, hoping for it for so long!
He leaned in, gave me a peck on the lips, then stood back up like he’d just been shocked. It felt like he’d had to work himself up to it and it was over before it even started! Not only that, but his Hit-and-Run Kiss was HARD — he practically smacked me in the mouth with that quick little kiss. I was so dazed, I had no idea what to think or say or do.
LOL (;
I have never had an awkward date (thank God)…but poor Rae, yours definitely takes the cake!
This is not exactly a date story. It is a pre-date meet the parents of the boyfriend story. I was in a somewhat new relationship and he thought that it was about time that I met his parents so I agreed to stop by their house before going out to dinner one night. I knew that they were super conservative (which I am deffinitely not) so I was more than a little nervous.
When I got there they were in the back yard by their pool. I shook hands, said hello and then made a comment about how beautiful their pool was. His dad told me that the temp. was perfect and that I should feel it. So I bent down to put my hand in and low and behold, I fell head first in to this pool, wearing a mini skirt no less. Everyone was half laughing and half horrified as they were all asking me if I was okay but just as I started to reassure them that, yes I was fine, his mother got a terified look on her face. I looked down and realized that the naked man playing cards had escaped their spot in my purse and were breaking the surface of the pool all around me.
There I was fully clothed surrounded by photos of naked men and flailing around in a gorgeous pool with the realizaton that my boyfriends parents would most likely never take a liking to me.
The relationship didn’t last but the hilarity of that first parental meeting will never fade!
desiree1612@hotmail.com
After a group dinner, one of the guys there asked me out for coffee. Sure, I said.
We talked, and he asked me if I noticed he was flirting with me all night. Not really, because he spent most of the night talking to other people. Would I have accepted coffee if [other guy] had asked me? Probably. Then he told me about his foot fetish, and informed me he was submissive and how did I feel about that? I babbled something about "well, maybe in the context of a relationship, but not what I want as the basis of one" because I was not prepared for that as a topic of conversation.
I excused myself shortly thereafter.
He called me the next day, and asked how I found the date. "Interesting." Then he interrogated me about what I meant by that, because he has found people use that as a catchall that means "not fun". Then he told me he didn’t think it would work out, because I had cats and he didn’t like cats. "That’s too bad, because I like my cats," I said, relieved that it would end so easily.
"How long do cats live anyhow?"
…
A few weeks later, he called back, telling me he knew we couldn’t date, but I had mentioned I was interested in a BDSM-type relationship. I actually argued about this for a while until I said that whatever I had mentioned then, I was not interested in it anymore, goodbye.
Seriously, you all are MAKING MY WEEK with your comments. Awkward dates FTW!!
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My most awkward date was when my friend brought me along on her date so she could set me up with her boyfriend’s friend (she thought I needed to get out more -___- ). We met outside of this pizza place and they introduced the two of us. I’ll admit that he was a bit good looking, he had that hipster swag going on.
Things were going well in the beginning, so she and her boyfriend left me alone with the guy. We had a good conversation going, I flirted and he flirted. It was cute and I thought maybe things were getting to the point where he would say the line "maybe we could do this again?" I was sort of waiting for that line for, like, the entire date and just as we were getting ready to leave and waited outside of the pizza place, he turns to me and asks (and I remember this part WELL) "hey can I ask you something?"
My heart was beating a little bit faster at this point because I was actually starting to like this guy. I mean, like, he was cute and pretty funny too. So of course in response to the fact that I find this guy sorta cute, my very hormonal teenage heart would decided to act jumpy at a time like that.
I answer back casually, "yeah sure", because I wanted to appear, you know, all cool and what-not. Well, since I was expecting that line, you all can expect the total shock I felt when he pulled out his iphone and asked, "which one of these would you pick as a birthday gift?" In that moment, I guess he saw my expression and somehow knew that I was expecting a way different question and cleared the air saying that it was for a girl he knew, but I could tell that the "girl" was really his "girlfriend". So that was where we both stopped – what I considered – flirting and stood there VERY awkwardly and VERY quietly while we waited for my friend and her boyfriend to come back (they were our ride). I kept checking my watch and phone, he did the same. We barely talked, only making small comments; he made one about the moon. Seriously, THE MOON. And we were in a shopping center, there were neon lights, shopping stores, and, well heck, a hobo in front of us and he chose to comment about the moon. That made the atmosphere even more awkward because his remark about the moon was BAD. "Hey nice, it’s the moon" and that’s it. He was quiet for the rest of the entire time.
My friend FINALLY came back after what felt like an hour. We said our goodbyes and good-nights; I said mine awkwardly and so did he. I later got the whole details from my friend a week later. Apparently the gift was for this girl he met a couple of weeks ago…one whom my friend’s boyfriend doesn’t know about because the guy and the girl are at that point in a relationship where they can’t really be considered boyfriend-girlfriend yet.
Later that night, my thoughts were just going crazy. I was totally embarrassed! I mean, like, here I was, just meeting the guy for the first time and already I was thinking about him asking me out again! Oh the humiliation! Especially the whole quiet and awkward scene in the parking lot., that was the longest awkward scene in my entire life. TOTALLY. AWKWARD.
I don’t have an awkward date story either, but MAN! Rae’s story is too hilarious!
I had a huge crush on a guy when I was in high school. He was a senior and I was a junior. Our first real interaction came when I was cast in a play as a character who stuttered. I also had to walk in on his character kissing "my teacher" & scream, something I was forced to rehearse for weeks. This awkwardness was clearly just foreshadowing for our first date.
My friend & I were going to skip a last period school assembly to go see a movie & she, unbeknownst to me, decided to invite her boyfriend, Adam, & my crush to come. They met me in the hall when I was still in my ugly high waisted wool pants, suspenders, feathered hat from band practice (most flattering outfit ever) and had to wait for me to go change. All three were seniors so could leave school without signing out. However, as a junior they had to wait for me while I called my mom to get permission to leave.
We went to see the Lord of the Rings and I sat next to the guy I liked. I started to realize that it seemed like we were on a double date and was freaking out with excitement that he was finally showing an interest. Everything was going well until Shelob, the giant spider, appeared on the screen. I have a chronic fear of spiders I went to cover my face just as he reached for my hand to hold it. The restult was that I smacked his hand into the air forcing him to punch himself in the face. I kind of wanted Shelob to emerge from the screen like the girl from The Ring & kill me then & there. I gave him my cold water bottle to hold against his face but the cap wasn’t on so water slushed all over him. He didn’t try to hold my hand again in the movie and I was convinced I’d blown it.
When the movie was over we had to drive back to the high school so the guys could get their cars since we’d carpooled to the theater. My friend asked my crush to drive me home and I was hoping I might redeem myself on the short ride to my house. He was quiet the whole ride so I was thinking I’d ruined the maybe, kind-of, possibly date.
To my astonishment he got out of the car in my driveway and came around to me. He looked me dead in the eyes and I was waiting for him to make some profound declaration about how he had feelings for me. Instead, he told me ‘Adam will kill me if I don’t try something’ & leaned in to kiss me. In spite of this completley un-romantic really-dude-this-is-your-pickup-line sentiment I still leaned in. His lips were about a half an inch away from mine when he stopped, straightened up and informed me that my backpack was still on & he ‘didn’t know what to do with his hands.’ I had to put it on the ground so I could get a quick peck on the lips (hands not touching me at all btw) before he dashed in the car and drove away.
In spite of all of that we actually dated for over a year but I can’t help but cringe whenever I think of that disastrous first date and my friend who ‘set us up’ still teases me about it.
So we were 16 and it was our first date and we decided to go see Jackass the movie. We had just settled into our seats and were chatting before the previews when we see all his buddies from school walk in. They sit way on the other side of the theater, so I’m thinking it must have been a coincidence. After a few minutes something hits me on the side of the head and I turn, and something else hits me in my face. The guys were throwing open packets of hot dog relish at me! It was all over me and I was so embarrassed I was about to cry. Well my date gets up walks over to them and gets in a fist fight with his best friend. Needless to say we got kicked out of the movie. 8 years later I married the guy that stuck up for me that night, and the guy that threw the relish was his best man!
Four Nipples…I guess that’s something you would want to know on the First Date.
I feel super left out because my boyfriend is also my first boyfriend and we didn’t do the whole Dine and Date thing. I do like to tell people about how me met though.
He was a friend of my ex-roommate and for some reason decided to come over at like 10 at night. While me and a girlfriend are in the kitchen getting drinks together I hear a bell. I look up and I see this guy who I just BARELY met riding a bike into my kitchen with a sombrero on his head like it was the most natural thing in the world. Two weeks dating we started dating and we’ll be celebrating Year 3 next week!
Here is mine:
I has just started dated a really nice guy named, James. We had been out for 3 or 4 for dates. So one weekend we decided to stay at my house and watch the movie Enchanted. I was sitting on his lap while watching the movie. There was a funny part and I laughed then accidently farted! YES on his lap! I was mortified and my whole face turned a bight shade of red. Then James said, and I quote – "That’s nothing. Ha, I can do one better! Then he farted, and LOUD! So we both ended up laughing about it and I will never forget that day.
- Beckie
ChiKittie (at) gmail (dot) come
I was drinking coke when I started reading this. I put it down the second i saw the warning….
Harry Styles has four nipples. DID YOU GO OUT WITH HIM EHMAGAWD?! The description fits!
So, there was this really nice guy. Smart and funny and handsome, too. We used to hang together with a bunch of friends, talked a lot, then one day he asked me out. YAY! Took me to dinner and then a movie, paid for it all, then we went for a drink.
GUY: ‘You know, I love talking to you and I have a really good time when we are together.
ME (blushing): Mhihmfihmfi (nodding and saying inchoerent murmurs)
GUY: there is this connection between us and that’s why I feel I can tell you everything. Never felt like this before.
ME (practically as red as a Ferrari): yes. Me, too.
GUY: So, I want you to know that.. I am gay.
…
…
…
I’ve never been on date, so I have nothing to share. But that is hilarious. I’ll remember that for future references to make sure I’m not going out with a guy who has something that embarissing. lol
When I was in college, a guy I didn’t know emailed me to tell me that he liked my shirt. He was in band with me, but I didn’t know him and he somehow figured out who I was. I ended up going to dinner with him and I should have known better because of his creepy stalking techniques. He took me to the local Denny’s, which is fine if you’re pulling an all-nighter with your friends. However, it does nothing to impress a girl you’re hoping to start something with. Things went from bad to worse when he made fun of me for not getting breakfast food (it was dinner time!) and not liking science (I was an English major!). When he finally took me back to my dorm, I told him that he could just drop me off at the door. He said, "You don’t want me to come up?" No, I don’t. When did I ever give the impression that I would be inviting you to my room?
Oh god, I have had many awkward dates but I think the worst one was while I was in college in Boston.
I had been single for about 2 years and totally in a dating rut and agreed to go out with this one dude because, what the hell, I was in a slump. I wasn’t that interested in him, but I thought I could get out my slump if I forced myself to go on at least a few dates.
Anyways, we were out to dinner and he wouldn’t shut up. He didn’t ask me a single question. I just sat there, eyes glazing over, listening to him go on and on and on about how cool his movie internship was and how sweet his apartment was, blah blah blah.
Finally, the dinner came to and end and it was time for the dreaded "good night kiss." I figured I owed him at least a peck because he bought me dinner, so as I closed my eyes and puckered up, waiting for his lips to land on mine, I all of a sudden felt a wet, slimey tongue in my ear.
No, he did not lick my ear. He sucked, licked, flossed, waxed and cleaned the whole side of my face with his mouth.
I was so shocked I froze in place, unable to stop the train wreck that was this goodnight "kiss." I just stood there, mouth opened, eyes wide, thinking to myself "this can’t honestly be happening. No seriously, WTF is happening right now?"
When he finished, about 2 minutes later, he stood in front of me, giving me this big goofy smile and nod like what he did was the sexiest thing in the world. I just stood there and stared at him, then calmly turned and RAN away. I never spoke to that guy again.
Ok, so I have a few. None of them are **terrible** per say, but they do illustrate how, in the past, I have had some weird dates.
(Keep in mind, that before I met my husband, I went on my fair share of blind dates through the invention of internet dating sites. This most likely explains the inevitable awkwardness.)
4. On my dating profile, one of my "turn-offs" was jacked up teeth. I live in the Deep South, so I wanted to make sure the guy I agreed to date had all of his teeth, that they weren’t nasty from dip (or meth) and that they were reasonably straight. This one guy stared messaging me and he seemed really nice. A little country, but he seemed genuine. At one point he inquired about my "no jacked-up teeth’ stipulation and what all it entailed. I should have known to be suspicious. We set up a lunch date and I walked into the restaurant (a crummy hole-in-the-wall burger joint with waitresses who looked like they hooked on the side to sustain their meth habit) to see this reasonably good-looking guy and thought to myself "That’s not so bad!" I am, after all, from the South and I can appreciate a fit man in a hat and Wranglers. Then he opened his mouth. He was missing a prominent tooth (brawling?), the remaining teeth were, uh, like a Picasso painting, and it was obvious he dipped. (Which is a disgusting habit. Spitting? And most of the time dippers carry around disgusting soda bottles to spit into when they’re in a place where it’s impolite to spit on the ground. Ewwww.) But I endured the whole date, trying not to look at his mouth, knowing I would never be calling this guy for a second date.
3. Another online suitor wanted to meet and he was intelligent and funny and I made sure to see an open-mouthed smile picture so I could check his teeth. He was cute and his teeth looked good. We decided to meet and walked around Wal-Mart (don’t judge – I was young and poor). He turned out to be shorter than me. Like, noticeably shorter. I’m 5’3" and I was wearing Chucks and he was still shorter. So even though he seemed really into me, the short thing was a deal-breaker. We walked around the store, me very aware that he was tiny. He looked like my little brother. The most awkward thing though was I liked him and even though I didn’t want to date him, I could see myself being friends with him, but it was hard to keep finding reasons to be unavailable when he asked me out so I just gave it up. :\
2. Another internet find! You’d think I’d have learned… This guy I didn’t know much about but he seemed nice so I invited him to come hang out with me at a diner where I knew everybody. He came in and he was a little geeky-looking. Tucked in, plaid, button-down, with pleated khakis and glasses. I could overlook that, because there’s nothing wrong with a little geek.
So we started talking and I realized we had nothing in common. He was a business student, very conservative, and he (no joke) was an active participator in Civil War reenactments. But that wasn’t the worst part. He farted. Loudly. And it echoed off the hard plastic booth he was sitting on. But instead of addressing it and making light of it he just pretended that it didn’t happen. Which made it more awkward. Then, he farted again. And ignored it. I ended our date shortly thereafter.
1. I was hanging out with my good friend at one of her friend’s houses. She had a crush on this guy and he was only in town for a few days, so she dragged me to where he was staying so we could hang out with him and his buddy. The buddy ended up being pretty nice. Long hair, played guitar. And I didn’t have to worry about the whole height thing because he was monstrous. Like, six and a half feet tall and over 300 lbs. He called me up the next day and asked if I wanted to go out to a movie and I said sure, I wasn’t busy. I drove out to meet him and we took his car to the theater. He drove a mid-nineties Camry. Have I mentioned that he was a giant? I still don’t know how he fit in that tiny little car. He was all hunched up and, I kid you not, his head brushed the roof. At the theater it was apparent that he barely fit into his seat. And he sweated. A lot. And his hair started to stick to his sweat and he was getting pit stains. I honestly can’t even remember what movie we saw I was trying so hard to keep my distance to avoid getting sweat upon. When we drove back to my car, Guy (yes, his name was Guy) made a move to kiss me goodnight even though I hadn’t made any indication that I wanted one. I had been actively trying to broadcast that I didn’t want one. I stopped him and said that I wasn’t interested in a romantic relationship at the time. Which I wasn’t. I genuinely thought he wanted to go out as friends. He was visibly upset and left. I was sorry that he’d gotten the wrong idea but figured that there was nothing different I could have done. Except to not go at all.
The next day I received an email from him telling me what a horrible person I was for leading him on, that he truly cared about me and thought I liked him too and how I was a tease and a whole manner of awful things. I stopped feeling sorry.
To be honest, my total dates = zero. So no, I have never had an awkward date, although I can say that the most awkward conversation with my best friend I had consisted of us meowing (yes, meowing like a cat) at each other. We are so awesomely derpy.
Thanks for all your amazing stories!!!
By going off the story with the most votes, I now proclaim JEATHER’S story as the winner!