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Happy Awkward Valentines

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Happy Valentine’s Day!  To honor the day of love, I got some great dating stories from a few of my Blogger friends.   Some are long, some are short, some are romantic, and some are awkward.  Please grab the popcorn (or heart-shaped box of chocolates or your kid’s valentines party candy) and enjoy!   Oh, and Happy Awkward Valentine’s!

happy awkward valentines

From Tauni Everett of SNAP! Creativity at Your Fingertips

You might think that you’ve been on terrible dates. Trust me when I say, your worst couldn’t come close to the date I am about to share with you….Years ago I was asked out by a smart, handsome guy. A medical student. Someone I REALLY wanted to date. Until I dated him.

 Let me sum up the evening in bullets:

  • I was picked up over 30 min late.
  • He had loaned his car to a friend and we drove in a small Nissan truck that I feared the flooring would fall out of at any minute, splattering us on the highway.
  • He asked me at dinner how soon I hoped to get married and how many kids I wanted…Awkward!
  • He took me for a walk to the roof of the city library after dinner even though I told him I really needed to get home.
  • We got locked out. On the roof. The library closed. It started to snow.
  • The officer that finally rescued us 30 minutes later kept suggesting we were “getting jiggy with it.”
  • When we got to his car, he’d parked in a no parking zone. The wheel was booted.
  • When he opened the door of the car for me so that we could wait for the towing company, he shut the door on the heel of my $200 boots. It broke off.
  • What the what?! After all that? He tried to kiss me at the door.

 Needless to say, we didn’t go out again.

From Kristi of Lolly Jane…

When I was 16 my bestie Robyn and I were invited on a double-date with some good guy friends of ours.  Surprisingly, they took us to the airport food court for dinner.  After we ate, they each pulled out some clear fishing line, a paperclip and a dollar bill.  We watched as they tied the fishing line onto the paperclip, then clipped it to the dollar bills and told us to hide behind the seats that lined each terminal.  We giggled as our dates tossed the dollar bills to the ground and snuck beside us stifling laughs as the people walking past would stop to pick up the dollar and jerk back in surprise when it moved.  There were actually people that would attempt to snag the bills more than a few times.  If they got it off the clip, it was theirs to keep and our dates would restring another dollar.  Hilarious!  We ended the night at 7Eleven with slurpees laughing about the tricks we played 🙂

From Casey Wiegand of thewiegands.com

How She Met Her Hubby

Chris is 4 years older than me so he was at my highschool graduation with his current girlfriend at the time (they were watching her little sis graduate). I am not sure how this came about but he asked who I was. smiley face. She told him… that is Casey Jones and she’ll be at Baylor next year. I graduate, make it to Baylor and Chris can name countless times that we were at the same places… always remembering who I was from that initial sighting. My sophomore year he sat behind me at a concert and tried to get the courage to talk to me the whole time and never said a word. Fast forward time….(he is older) he graduates, moves back to Dallas. I still don’t know he exists and we have still never officially met.

 I graduate college in August. One night Chris was at a highschool football game with a bunch of guys and my little brother, Travis, walks up to the group. Chris asks who that is…”Casey Jones’ little brother” (so I am back on his mind)…then later that evening we both randomly wind up at a Kanakuk reunion. He waited at the bottom of the elevators to talk to me and I took the stairs!

Finally he decided just to get my number and call me. What was supposed to be a phonecall for a “sort-of” blind date turned into hours of conversation. I didn’t even know what he looked like at the time. I remember when I went to answer the door, my heart literally stopped….I could not believe someone so handsome and so sweet was standing there.

I tend to be a bit of a homebody. And I remember my brother saying to me one day – “youre never going to meet anyone staying home all the time”… and my response was, God knows me, He knows how I tick… if He must, He will bring him to me.  And He did!

From Linda Gardner of Craftaholics Anonymous

My birthday is on Valentine’s Day {yes, I LOVE having my b-day on v-day!} so when my hubby and I were dating in college, he arranged the most amazing weekend ever for my birthday/Valentine’s Day! He had a connection for a free trip to Vegas in a private jet. {yeah, he had a really awesome roommate!} So we flew to Vegas for the weekend and stayed at his parents house. On Valentine’s Day, he made my favorite breakfast and thanks to another connection he had, gave me a flower arrangement made by the flower designer at the Bellagio. Then he made my favorite dinner and we went to the Bellagio to watch the fountains and walk around. It was the most romantic, thoughtful date ever!

From Whitney Ulrich of A Mommy’s Life With a Touch of Yellow…

My senior year of high school a girl I worked with (who obviously did not know me very well haha) wanted to set me up on a date with one of her single friends. I was getting excited but kind of nervous since the first time I meet this guy will be on our set up date. I have no clue what he looks like, what he likes, nothing. But I thought at least we are just going to a movie, super low pressure, can just enjoy the movie and don’t have to talk much, which makes it much less awkward. I just have to bring up enough to talk about for the car ride there and back and I should be set.

Date night comes around, he picks me up in Layton and tells me we are going to the movie in Salt Lake. Weird I thought since there are plenty of movie theaters here, but I played along and just got enough going in our conversation to get there. He was a bit weird and from what I could tell not so much my type, but I was there so I was going to make the best of it. After all hopefully the movie will be good, and then after that if I don’t want I don’t have to ever go out with him again or if we had fun we could. It was no pressure. We get to the theater in Salt Lake and there is a huge line for something. I thought well I’m glad I don’t have to stand in that line, whatever it is.

Here is where it gets awkward, he leads me over to the line and I see it is the line for the opening of one of the star wars movies. I should have known he is a star wars geeks (after all he was wearing a long sleeve plaid shirt tucked into his jeans in the summer, but I gave him a chance anyway). I am not much of a fan of star wars lets make that perfectly clear. So the rest of the date consisted of standing in line for TWO hours for a movie I did not want to see (which he did not warn me or tell me about before he picked me up or even before we got there, I think he was trapping me into it and I was too nice to say no), watching a three hour movie I did not want to see, feeling awkward the whole time because he was clearly feeling it ( he was trying to hold my hand the whole time) and I was clearly not, him talking all about how he wished he would have dressed up for it, and the whole ride back to Layton talking all about the movie I didn’t even pay attention to.

Oh my goodness it was so awkward. I laugh about it now and it is funny to tell the story but seriously who doesn’t tell their date that they are going to a movie a 1/2 hour away, stand in line for two hours and doesn’t tell you what movie it is? Star wars fans that’s who. Safe to say we did not go out again (I am sure he found someone but it was not me), and I did not go out on any more blind dates.

From Vanessa Goertzen of Lella Boutique

I think the most embarrassing thing I ever did was cheat at bowling because I was nervous to kiss a guy. (He had put forth a deal that if he won, I had to kiss him.) I had never kissed anyone and was terrified I would be bad at it. To make sure I won, I hit the “strike” button before my turn so it would give me the points AS IF I had gotten a strike, ha ha ha! I was so terribly shy around guys, I always seemed to do very backward things like that. I guess that’s one reason I knew Kevin was the one for me–I could be my normal self around him

From Mandy Beyeler of Sugar Bee Crafts (okay technically this is written by her husband!)

Early in my freshman year of college, I was set up on a blind date through a buddy of mine who had quite different tastes than myself. I was a bit worried. Thankfully, the date went surprisingly well, and I quickly thought about how I could arrange a second date. Of course, with second date, I had to raise the bar a bit. A blind date can fail and be written off as just another blind date gone awry, but a second date is intentional, and can make or break a potential relationship.

Being the savvy, manly, and independent 18 year old that I was, I concluded that I should invite her over to my place for dinner, which was a great plan except for the minor detail that I still lived at home with my parents and two younger sisters. I suavely arranged for them to be out of the house for an evening, and set up a double date with the lucky lady, her friend and my buddy.

I planned a lovely meal of oven broiled steak, macaroni in a light white sauce, and fresh green salad.  My buddy arrived early to help with the final preparations. While I gently tossed the greens, he wandered over to the macaroni and white cheese sauce and said something about it not having enough cheese. Before I could react, he grabbed a massive handful of cheddar cheese and dumped it into the pot. My macaroni in light white sauce was now good old fashioned mac’n cheez. Wonderful. Just then, the girls arrived. Knowing it wouldn’t take long for the steaks to broil, I put them in the oven and proceeded to welcome the ladies to my humble abode. We took their coats, sat around the fire and made the usual small talk.

The small talk must have went very well, because before long we noticed a slight burning smell, followed by the unmistakable sound of a smoke detector. I bolted into the kitchen and learned the live long lesson that broiled foods must be watched, grabbed the smoking pan of meat, and ran out the front door in a futile attempt to save our lungs for our now vegetarian dinner. Being the good sport that she was, my date ate the mac’n cheez and salad in good humor, the slight haze in the room only making her all the more alluring.

Following dinner we settled down for a movie. I sat somewhat stiffly next to my date, close enough for her to know I was there but with enough space for her to know that I was a gentleman. Midway through the show I decided to try my luck and hold her hand. I inched over a bit, waited for 30 minutes, and then reached out my hand. She held out her hand in return, but not in the receptive “I’m-so-glad-you-want-to-hold-my-hand” manner so much as the “I’m-so-glad-you’re-handing-me-something” shape. It quickly and awkwardly dawned on both of us that we had a mutual misunderstanding of intentions. Either because she felt sorry for me, or because I had no M&M’s to give her, she relented and held my hand for the rest of the movie. And the rest, as they say, is history.

From Kelli Rich of The Turquoise Piano

We were walking around Lisbon, Portugal to see some sights when seriously, out of nowhere I had to use the bathroom so badly it hurt.  If you’ve been to the city before you know that there are no public restrooms.  We pretty much ran from place to place asking if they had a restroom.  The answer was always “no.”  I was like “okay I’m going to have to go in the street unless we can find a McDonald’s or something” when we stumbled upon a church.  We walked inside and there was a table and a lady there.  She asked us if we wanted to see the cloisters.  The first thing I said was, “does it have a bathroom?”  It did!  Then I asked how much it cost.  We paid like $5 to see a bunch of tombs.  Well, I paid to run to the bathroom.  So I went in there and used the facility, THEN noticed there was no toilet paper.  AND there was no soap.  I did the best I could using only water to wash my hands and when I told my fiance he laughed for a while and dumped a bottle of hand sanitizer on me.  We just had our 6th anniversary.  

From Kristen Duke of Kristen Duke Photography

The most awkward first date I ever had just happens to be with my husband. Funny enough, we dispute over whether or not it was our first date. I asked him to come along with me to meet a friend and her boyfriend. Though I had a crush on this cute boy, I didn’t want him to think it was a date, just “accompanying” me. I drove us in my brothers car about 45 minutes from our college town to the big city to meet my friend who lived several hours away. Way back then (15 years ago) we didn’t have GPS or cell phones, so navigation was tricky if you didn’t get directions previously. We basically drove around in circles for a few hours until we finally found the meeting spot. I felt totally awkward as the driver and he tried to make awkward conversation about how it wasn’t so bad that we were so late to meeting my friend. After all of that, we only got to see my friend for about 5 minutes, then she had to go. We drove back (awkwardly) to our college town, and I figured this crush on this boy would diffuse, and he’d hopefully forget what transpired that night. Who would have guessed that 2 years later we’d marry, and 15 years later we’d have 4 children! I’m typing out my emotional love story chapter by chapter on my blog, I’d love for you to come read along!  Sometimes those awkward first dates really do work out!!!

Happy Valentines Day!
And finally I have an awesome story of my own.  This was embarrassing and awkward in one.  
I used to work at TGIFridays as a hostess.  One day in December, a new server named Rick started working there and I thought he was pretty cute.  I came up with a master plan to get him to ask me out, as I did with my conniving manipulative ways bwahahaha!  I would go to dinner at Fridays with a group of friends and have them ‘meet me there’ and go in before me, request to have Rick be their server.  That way it would appear that they were just friends with him, and I could keep my dating life a little more private amongst my co-workers.  I would casually walk in and then flirt with him the whole time he was serving us.  
The plan backfired.  My friends walked in and for some reason RICK himself was seating tables as well as serving and they walked right up to him and said “We want to sit in Rick’s section.”  He said, “Um, I’m Rick.”  That was incredibly strange to him, I’m sure.  But when I walked in and joined them, it all made sense to him and he smiled this giant smug smile at my not-so-smoothness.  But he did ask me out.  And the first date was very awkward.  
You know how in movies they have those montages of people going into dressing rooms and coming out in all these funky outfits and upbeat music plays?  I think that happens in every single Disney Channel Original Movie.  That is what he was envisioning for our first date.  He took me to the mall and MADE me try on outfits.  It was. so. weird.  We shopped around at some other places, including spending about an hour watching him find the perfect athletic shoe.  He finally took me home and invited himself into my apartment.  “I’m so tired…” I said, sitting down on the couch, hoping he would take the hint and go home.  He sat down next to me and started kissing me all over my face.  Seriously?!  He’s already jumping to kissing me.  If anything made me put my guard up, its physical action before I’m ready.  Finally I told him I had to get ready for work so he left, at last.  Blech.  
What was your most awkward first date?  What was your best or worst Valentine’s day?  I’d love to hear in the comments!!  Happy Awkward Valentines!


  1. Oh boy, I’ve had some doozies- like the time my date started dancing BY HIMSELF, WITH HIMSELF. Yes- he was the only one on the dance floor. Oh, and did I mention, it was a SLOW song? That was awesome. But then there was the time I went on a “casual” first date- to see the BYU symphonic orchestra and choir perform- in the Tabernacle. I was in jeans and boots because I was told it would be casual. My date wanted to find a family from his mission who’s daughter was performing- left me alone for 20 minutes until he found them, then the rest of our date was spent with them. I finally told him I had to go home and do homework. It was a Friday night.

    1. Heidi @ Honeybear Lane says:

      Haha–that’s classic Amy!

  2. My most awkward date ever was with a guy {can’t even remember his name now} that use to come in to the store I sold furniture at when I was 18. He came in all the time buying random furniture, it became obvious to myself and all the other employees that he liked me. I mean who comes in every week to buy furniture? Seriously!? He was pretty cute though, and I hadn’t ever dated anyone before. So when he finally asked me out he asked if I wanted to come over to his house. So I showed up at this house that was located in downtown Mesa, AZ … it was located next door to a mortuary! He lived in the house on the mortuary property! He thought it was a good idea to take me on a tour of the actually mortuary! We walked through everything, where they embalm people, where the cremations took place {even opened the door to it, still bones inside}, etc… There was actually a funeral going on at the time too! Then he took me over to this incredibly old creeky house showed me around. As we sat down on his couch he pulls out a joint and asks if I smoke weed!?! “Uhm, no” I replied, then nicely said I needed to go home. That’s was the end of that! Interesting to say the least.

    1. Was any of the furniture he bought in his house??

  3. These are great stories! My most awkward Valentine’s Day: I had been dating a guy that I really liked (looking back it was a superficial thing–he was very very hot!) but we had only been going out for a short time, like 3 weeks. I said we should ignore the holiday to take the pressure off of each other about what we “were” etc. He agreed. Again, I think I probably only said that so I wouldn’t be disappointed if he didn’t do anything. Anyway, we went home from school to my college apt for dinner and a movie. My roomates had left for a few hours and everything was going well. I stepped into my room after dinner to brush my hair/ fix my makeup and I saw a cute teddy bear with a heart/ rose laying on my bed. I ran back to thank him for the Valentine and gushed at how sweet that was of him….uh, turns out he didn’t leave it for me. My thoughtful roomate (my best friend) left it for me instead. Ugh. Very embarrassing.

  4. I had a friend that I studied with all semester. At the end of the semester he asked to take me out to dinner during Christmas break. A couple weeks later he picked me up for dinner and on the way there the got a phone call. He asked if it was OK if he answered it. I didn’t mind. The conversation sounded a bit tense. I asked him if everything was OK. He said there was a family issue because someone had eloped. I asked who. He answer with, “Me.” It was then I noticed the ring on his left hand. I was stunned and didn’t have anything to say for minute. He reassured me she knew we were going out to dinner and was OK with it. He didn’t want to back out since he had asked be before they had eloped and that we could still go out as friends. I don’t remember a whole lot other than it was an awkward dinner. He opened my doors, paid for dinner (even though I kept insisting I would pay for my own), and he even walked me to the door. We stood at the door all awkward like (at least I thought it was awkward), so finally I hugged him and congratulated him on his marriage and wished him the best of luck. As soon as I got in the house I called the other guy I had been dating casually (my now husband) and told him what had happened. We laughed about it and he then admitted he was glad because he didn’t want me dating anyone else anymore.

    1. So it wasn’t Valentines, but since I don’t really ever celebrate Valentines, it was the best I had. Hope that is OK.

  5. I was set up on a blind date with a firefighter. I thought, whoa, this is going to be awesome, right?! I wasn’t sure exactly what we were going to be doing, but I knew a movie was involved. I hadn’t eaten all afternoon so that I’d be ready for dinner or atleast popcorn 🙂 I was dressed really cute, had my nails done (which was the first time I’d ever had them done and I spent $60 on them!). So, the guy came to my house, late. When I opened the door I saw a short guy (I’m tall), casually dressed but wearing these hideous black velcro orthopedic looking tennis shoes. Hmm.. He took me to a movie but when it came time to pay he didn’t have enough money. Looking embarrassed he used some movie coupons he had to pay for our tickets. Hmm.. As we were approaching the concession stand he turned and walked right past the counter and into the theater. Oh, my stomach was a rumblin’ then! I’m sure the look of disappointment on my face was quite obvious. We watched the movie in welcomed silence. Afterwards, we went back to his blazer while he proceeded to go directly to his door. Ok. I stood there waiting for him to get inside and reach over to unlock my door. Then we wen to the gas station. Mr. Firefighter left his engine running while he filled up with gas, got inside the car and reached over to the bench seat to grab a half full bottle of water laying there. He took a drink and offered some to me. I politely refused. Then he reached over me to the dashboard and grabbed some breath mints (which he was in desperate need of), took some and offered me some. Again, I refused. Finally we left and he drove me home. He followed me inside where he sat almost on top of me on my couch. He then told me about how he lived with his mother in a duplex, that she was a controlling and independent single mother. He told me of his 3 car garage he had built on his property (must have been what all his money was tied up into!). And then sat there for hours talking about himself. By then my stomach was eating itself from starvation and I couldn’t get rid of this guy!! Needless to say I never saw him again!

    1. Heidi @ Honeybear Lane says:

      Haha! Great story! Thanks for sharing.

  6. Such fun (awkward!) stories here!

    My most awkward date had to be the first date with my high school sweetie. I was 15 years old, and there was NO WAY my parents were letting me go out with an older boy (who could drive) by myself. In order to go out with him, I had to double with a friend.

    My best friend brought her boyfriend, and my date brought a guy friend who, in turn, brought TWO girls (neither of whom he was dating….it was so weird).

    We went to a local pool hall, and the two girls ended up trying to flirt with my date the whole time. I think I spent the whole time hanging out with my best friend and her boyfriend because the girls were VERY annoying.

    My date ended up having to drive everyone home, and we got pulled over for having waaay too many people in the car.

    The redeeming part of the whole date was when he drove my friend and me home. He and I actually had a chance to talk with one another. We ended up dating for over 3 years after that! 🙂

    1. Heidi @ Honeybear Lane says:

      Glad it turned out well anyway! I hate those dates though! Thanks for sharing.

  7. WOW just what I was searching for. Came here by searching for sessiors

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