The Most Awkward Date. Ever.

Today's post is a little bit different. At Hiccups, one of my main goals is to give you content that makes you laugh. Currently, I am lying on my couch, where I have been for the past six hours, battling a stomach flu. If I wrote anything funny, it would likely come out gibberish because #fever. Try not to be too jealous.

So naturally, I had to ask Shannon from shanndelier to swoop in and save a blogging sister. Check out her story below, because it is wonderfully awkward. I shared my own awkward date story over on her blog here, so read into that as well. It's called "Date Stains" if that's any incentive to you ;)

Anyway: presenting Shannon!

Hey there! I'm so excited to be here on Chaun's blog today and to be sharing this truly incredible story with you. But first, a little bit about me. I'm a foodie and outdoor-adventurer living in Salt Lake City with my husband, who is also a chef, and my dog, a little black and tan shiba inu. By day I'm an account manager at a marketing agency and by night I blog over at

Now, to the story. A few disclaimers: Names in this story have been changed. I don't think this guy is/was a bad guy, he just definitely did not nail this date. I literally have no pictures to go with this story, so bear with me. It's a good story on its own, though.

One day, all the way back when I was 15, I was in driver's ed. We were seated in alphabetical order, and I ended up sitting next to this guy, Alex. He was nice enough and we talked often, but nothing deep or personal. Then, on a fateful day in February, we discovered that we had the same birthday.

"Come up to the front," the teacher said when he found out. We faced the class, embarrassed. He went on. "It's tradition that when two students have the same birthday, they have to kiss." I looked at Alex, mortified. He didn't look at me, but he was blushing. "I'm just joking!" the teacher said as the class roared. "Sit down!"

Fast forward another two years. I hadn't talked to Alex much since driver's ed. Now I was 17, nearing the end of my senior year, and I got a Facebook message.

Alex: Hey.
Me: Hey, what's up?
Alex: You remember that day in driver's ed when the teacher wanted us to kiss?
Me: Yeah...
Alex: I wanted to kiss you.

Keep in mind that I hadn't talked to this boy in years (plural) and even before that, we were only platonic acquaintances. At this point I had literally no idea how to respond.

Me: Haha, bummer.
Alex: Anyway, we should go on a date sometime. What are you doing Friday?
Me: What do you have in mind?
Alex: I was thinking we could make cookies and maybe go stargazing or something.

So, this is a weird conversation, right? I mean, I'm not the type of person to say no to a first date even if I do get asked out over Facebook, but a stargazing date sounded strangely intimate for someone I barely knew. Plus, he had just told me he wanted to kiss me, so, even weirder.

Me: Sure, I can go.
Alex: Okay, cool. I'll pick you up around 8:00.

Friday came, and I had just finished getting ready and was sitting in my kitchen eating a snack and waiting for Alex. I was a little nervous because of the previous conversation, but mostly curious as to what was going to go down. A few minutes later, my brother, who had been outside shooting hoops, came inside.

"Some guy named Alex is in the driveway asking for you," he told me. So this was how it was going to be. I grabbed my bag and went outside to find Alex in his tiny white pickup truck with the window rolled down. I hopped into the passenger side.

"So, we just gotta drop by my house to pick up a few things, and then we'll go pick up my cousin and his girlfriend and head up the canyon," he said. All of these things took me by surprise. I had no idea that this was a double date or how two more people were going to fit into the tiny two-man cab. And apparently the "making cookies" idea was completely out the window. I decided to just go with it.

We stopped by Alex's house where he threw a bunch of pillows and blankets into the back of the truck (bad sign), and then headed across town to pick up his cousin. Once the four of us were smashed - literally, smashed - into the truck, Alex headed up the canyon. And up. And up. Soon, he turned off onto a dirt road and kept driving until we came to the end of it. I was literally in the middle of nowhere with three people I didn't know and no cookies.

"Where are we?" I asked.
"Just the best place for stargazing," was the answer. "Let's hop in the back."

If I thought the cab of the truck was small, the bed was even smaller, and I wasn't sure how that was possible. With the four of us, there was no room to move, which made for a forced cuddle with the mysterious and falling-out-of-my-good-graces Alex. I was not a fan, but I was sure it couldn't get much worse. I was wrong.

"So, how many guys have you kissed?" he asked immediately. I was appalled. Why would he ask that? Why? How was I supposed to respond?

"A couple," I offered vaguely. I had just ended a relationship that had lasted about a year, and he knew that, so it seemed like a safe answer. "Why? How many girls have you kissed?" I threw back.

"None," he said, which I immediately knew was a lie. He was trying to pull the oldest and lamest trick in the book - pretending he had never kissed a girl so that I would be compelled to be his first. Does this ever work? Like, ever?

"Why not?" I decided to play along. I mean, I had nothing to lose at this point. Obviously I wasn't going to kiss him. It turned out to be the wrong question to ask.

"Well, I had a chance, but it didn't work out. This girl was crazy." FYI, for all girls dating out there: if a guy ever tells you his ex was crazy, and then launches into a long story about why and how wrong she was, run. 99% of the time, he's the crazy one, and soon he's going to be ruining your reputation by telling everyone you were crazy.

Anyway, the next three hours of the date (aka the whole date) turned immediately into a long, sappy story about this girl he used to like, but she broke his sad little heart and blah blah blah. I'm not even joking. I suffered through this for three straight hours in the back of a tiny pickup truck in the middle of nowhere. And the best part of this story was: he had met this girl at EFY. At age 14. For real. (If you don't know what EFY is, it's a church camp for 14-17 year olds where you read scriptures, attend devotionals, and occasionally develop premature romantic feelings for pubescent humans of the opposite sex. It lasts for five days and the common name for those feelings is the COW - crush of the week.)

I basically had to stop my eyes from falling out of their sockets because I was rolling them so much. On the ride home, he was still trying to convince me that he had never kissed a girl, and that wouldn't it be great if I was his first? Needless to say, I didn't kiss this boy. I didn't go on a second date or even have a second Facebook conversation. I did, however, have a second cookie when I made them myself later.

Shannon | Blog | Instagram | Twitter

What's your most awkward date you've ever been on?


  1. I can't decide if I want to laugh at the kid or cry because of how clueless he was. Oh man. Shanna you're a champ! haha.

    1. Both are totally acceptable here ;) Shannon is awesome. Not only did she give us some good "how to know to avoid these kind of guys" tips, but also kept our hearts focused on achieving promised cookies:)

    2. Haha the date was bad but it makes for a great story, so I have no regrets!

  2. You are so right about "the crazy" conversation. Yes, run. Run like the wind!

    1. I feel like Shannon gave us many solid advice tips, including things about running from undeserving boys, and making sure those cookies keep priority on a Friday night

    2. That piece of advice has never done me wrong, haha. I mean, sometimes it really is the girl that's crazy, but hopefully they're not talking about it on a first date!

  3. HAHAHAHAHA I love how the cookies were your focus the whole time. That would totally be me. How awkward for him to invite other people and not tell you! You should always know when a double date is going to be sprung on you...

    1. Shannon is probably one of my fav bloggers for this reason. Cookies and food are a top notch priority.

      He probably should have also told her that cookies were in fact not a part of the evening plans. :)

    2. Those cookies were the only thing giving me hope for this date, plus, #constantlyhungry over here. I don't mind being surprised with a double date as long as the vehicle is big enough to comfortably transport all four people, which in this case, it definitely was not.

  4. OMG! This great and now I have to check out your blog as well. I have had too many horrible dates to share but my most recent was Saturday when a guy from okupid and I met for drinks... his profile said 28 he was 34 and after seeing the real life version I'm pretty sure the pictures are from when he was 26 lol.
    After 2 drinks and awkward conversation I told him I was tired and need to go. He walked me to my car and goes, "What are you going to do?"
    "Go home."
    "You inviting?"
    Um no old stranger..."No I'm going home ALONE."
    'Can I have a hug."
    The dirtiest feeling I've ever gotten from a hug (and i only used one arm) he squeezed tightly and says, "That feels good.!"
    My favorite line from this blog, "there I was with 3 people I didn't know and no cookies".. would have been my thoughts exactly.
    Hope you feel better Chaun

    1. Oh gosh. That is so creepy! Shannon met her hubs on OkCupid, and it worked out wonderfully. Bummer that your date didn't work out (although maybe that's a good thing, because #nocreepsherethanks.)

      Thanks, feeling much better :)

    2. I was just about to say I met my husband on OkCupid, but looks like Chaun beat me to it. :) There are SO many creeps on there though so I feel your pain! I can't believe he lied about his age... I would have been like nope, bye, too.

  5. I love stories like these. I mean every single girl I know has had one. They never ever get old.

    1. No ma'am they don't! We'd love to hear any of yours you're willing to share :)

    2. So true. I have many more in addition to this one as well!

  6. Hahaha, this is a great story! Thanks for stopping by my booth during the lull on Saturday Chaun, now I'll hop over to Shannon's and read your story :)

  7. oh HI! I didn't even that was you commenting. Thanks for your super cute handouts at the conference. We got the date idea to put the kids in front of the tv with pizza, while we adults have olive garden. Great idea. I'll check out your blog as well :)

  8. Wow, that was painful to read. Although now that I think about it, you should be glad there was another couple there. It would've looked a lot like the opening scene of a CSI episode if you were alone!


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