It’s been years since I wrote a painful-but-true Valentine’s Day post, so I thought I’d dust off the ‘ol corners of the brain, and pull out the EMBARRASSING MOMENTS file for your stupid holiday pleasure. Enjoy.

Flirting on the phone with strangers

Making connections. [Chiang Rai, Thailand, 2014]
Back in the day, we used landline phones. Sure, you could pay extra for caller ID or you could dial some numbers to discover what call you missed. But for the most part, you picked up, especially if you had roommates.

When I lived in Eugene Oregon, I lived in a house full of characters. And one day I answered the phone and started flirting with the guy on the other end. Now, just to give you some history, I had been doing this for some time. Call it pathetic. Call it overconfidence. Originally, I think it was born out of those long calls where you and the other person are on the line while some credit card or telecommunication ordeal was getting sorted out.

So I’d start asking questions. Where are you calling from? How’s the job? You know that sort of thing. Small talk. On this particular day, the guy was calling about the room for rent. My landlord Connie was looking at me incredulously as continued to twirl the phone cord around my fingers and giggle with a man who I had never seen or met.

Well, we really hit it off, so he decided to come on over to the house and go have coffee or something. Connie told me that I needed to be careful and that basically I was nuts. I was high over the flirting and excited to see what the mystery caller would look like. He sounded so sexy!

I didn’t have to wait long. I ran over to the door after it rang, Connie close behind me. And when I opened it I was gutted. There was a short, bald, much older man standing there. Connie, on the other hand, was over the moon. “You kids have fun,” she said as she pushed me out the door.

Deflated, I reluctantly had coffee with him. My mind was frantically trying to figure out how to get out of this. Then, I realized I had to go through with this impromptu date. The disappointment was on my face. I felt bad. I felt shallow, but ladies and gentlemen, he was…not was I expected, and I never flirted with a strange guy over the phone again – unless he lived in a different state.

Imaginary bird watching

Is that a bird? [Wat Chtuphon Chiang Rai, 2014]
This took place when I also lived in a house full of roomies in Durango, Colorado, but this time it was all guys (I wouldn’t recommend it). The cleanest guy was moving out and I’d be taking over his room. So there you have it. I lived among swine.

Okay. If Eugene is known for its eccentric residents, Durango is known for its outdoorsy types. So the guys did those kinds of things. But one of them was really weird – and he liked me, of course. He was a carpenter who would use his band saw in his bedroom. I’d hear the dang thing at crazy times during the night and imagine sawdust flying everywhere onto his carpet. I’d wonder what in gawd’s name is he cutting wood in his bedroom for???

He’d also walk around shirtless. To be fair, he had a really nice body, washboard abs, tanned, hair longer than mine, down to his waist, and he wore glasses. He was also short. I tell you these short guys are brimming with confidence. Let’s call him Lumberjack Dan. One time he asked me, “What makes you laugh, Lani?” and I thought that was the strangest question. When I told my best friend, Nadya, we laughed and laughed over it.

Anyway, I agreed to go out on a date with him. But you know it’s not going to be a typical date. You know that, right?

Dan was an avid bird watcher so he was going to take me out hiking in hopes that we would see some birds. Okay, by now, I had been living in Colorado for about five years which meant I had gone on my fair share of hikes and outdoor excursions. So on the day we head out, it’s early, he drives me in his truck, and we start hiking.

Remember those abs? Yes, Dan is a healthy man who is like a mountain goat climbing up, while I’m like a cat who can do it, but who’d rather be napping. My friends, it was a long ass hike – up. Every once in a while he’d get close to me and we’d look up at the trees, but we never saw any birds. It was almost as if all the animals decided to scatter because they knew Lumberjack Dan was here.

Several times during the hike, I’d wonder if he required rest or water because he was unstoppable. I contemplated whether he was trying to ‘break me’ because the hike was incredibly punishing. And I considered that this was the area they would find my murdered body because I was too stupid to see the signs of a psychopath killer.

That unromantic moment

Don’t stand so close to me. [Bangkok, Thailand, 2007]
After high school, my prom date decided that he wasn’t really in love with my best friend (am I getting more pathetic in your eyes yet?), that I was alright, so he asked me out on a date.

This is the same guy who serenaded me on the high school’s front lawn – a birthday song that he penned himself. All my friends thought it was the sweetest thing, but I knew he was in love with my best friend and was doing this just to impress her. I know this because Nate and I had many conversations about his love for her before 6th period class.

He wanted to ask her to prom, but another friend asked her first, so I was his second choice.

He was going to take me to a local carnival, but the butthead was incredibly late. Like super late, like so late, I called his phone (landline) multiple times to find out what the heck was going on. I think his mom answered and that ended that. By the time he called back, he explained he got off work late or something like that. By then I was fuming and wanted to call it off, but he insisted on coming out to make it up to me. So an hour later (no I’m not exaggerating), we head to the carnival.

Nate continues to try to make it up to me by trying to win me a prize like a teddy bear, but he can never get the ball in, or the pop the balloon with his darts. It turned out to be a pathetic evening of wasted effort and I found myself becoming one of those girls who rolls her eyes at guys who can’t do anything right.

Now I realize your sympathies lie with him, but wait, please. After he takes me home, we stand awkwardly in front of my childhood house. I want this evening to end, but then begin to realize that Nate is trying to make a move on me. And when the moment arrives, do you know what he does? He burps. No, it wasn’t a beer belch, but it was something he definitely got out. Then he leans in for a kiss. I laughed and back away. I said, “You can’t burp and then try to kiss me!”

Nate then has the audacity to act shocked and confused, and so I have to spend another 30 minutes or so explaining to him why burping before going in for the kiss is not kosher. Then he tried it again, but the burp remained seared in my sound memory.

He went home and we never went out again.

Now it’s your turn! What were some of your weirdest dates? Happy un-Valentine’s Day!

21 replies on “Awkward weird dates, I’ve had a few…

  1. Laniiiiii, one more time: the way u write makes me feel like we r bffs! I have flirted with stranger on the phone, thought it was the day I’d get murdered but never went out with my friend’s exes (they didn’t think I was good enough?!). Love this post, keep them coming! Also to ellaborate more on the vote (meh dates), I have had meh dates but shitty-ass exes, which is worse 😓

    Liked by 1 person

    1. I hear you. I’ve dated a few good wieners. But I feel like I had to, as strange as that sounds. It’s like having to get burned so you don’t do it again. Of course, you do – but I figure sooner or later, you’ll figure it out. Right???

      Thanks for the love, K! xo


  2. Your stories make for fun, hilarious bedtime reading.

    It’s been a long time, so I’ll just mention a few now faded memories. There was the game warden. (I have no idea how I met him.) He took me shooting in the woods one day, and I did really well even though I’d never shot a gun before.

    There was the really, really sweet marine drill sergeant. (Does that sound contradictory?) I met him when a friend and I came back from an overnight bicycle trip on a ferry. The battery on my dad’s truck was dead, and he jumped it. I dated this drill sergeant for quite a while, but he was just too sweet.

    Then there was the milkman. He must have been the last milkman ever. I have no idea how I met him or who he delivered milk to.

    Liked by 1 person

    1. Hahahha. These are good stories, too. I love all of them because they are so unique. 🙂 Yes, the sweet drill sergeant is contradictory. Maybe he need to balance out his daytime job personality 😉

      Liked by 1 person

  3. Many years ago, I worked up the courage to sign up for I browsed around, found a nice-sounding guy and emailed him. As we were chatting back and forth, he mentioned that he had a dog, then he emailed me a picture of the dog and I was like, “That dog looks familiar.” Turns out this guy lived in the house directly behind mine and I’d seen him outside many times with his dog! We went out for a drink the next night and I immediately knew I wasn’t into him. Too late though: I had acquired a quasi-stalker and he lived in a house whose windows looked directly into mine. Awkward. It was uncomfortable for this next couple of weeks but he did finally decide to leave me alone when I told him I’d met someone else (which wasn’t actually true).
    Anyway, great idea for a post!

    Liked by 1 person

    1. Hahahahaha! Great story. OMG. It’s so funny how these crazy things happen. Truth is stranger than fiction. I’m like, the dog looks familiar? Where is this going?

      Thanks, Heather!

      Liked by 1 person

      1. Hahahaaaaa. Yeah I had actually forgotten about this story until recently until I was at a table with a bunch of women sharing funny online dating mishaps.


  4. I was convinced that my hometown crush also loved my best friend. Although in hindsight, I think he just talked to her because I refused and she was actually the second choice…. or maybe my ego has just grown enormously, so my perspective has changed, haha.
    I once went on a date with a hardcore communist. Like that was his nickname to all my friends when telling the story. “The Communist.” And while I have no real issue with communism in theory, in practice, it’s a mess… so I tried to explain this distinction to him, and he was just like hardcore touting communism’s merits and I was like “ugh ok whatever.” It wasn’t even just the unrealistic nature of his values, it was also his hardcoreness. Like he was right and I was an idiot for not seeing how beautiful communism was. And if I remember correctly, he then tried to make out with me in the bar, even though we clearly didn’t like each other all that much, and I was just like “seriously?”

    Liked by 1 person

    1. Oh! And I forgot my Craigslist date, bahaha. I once made a Craigslist ad for someone to take me to a movie and buy me peanut M&Ms. And someone did! But I had also said that I would hold his hand if he did it. (The ad was ridiculous lol.) So during the movie he tried to hold my hand. But I wouldn’t do it. Because I was super immature at that time, hahaha. Oh God. That’s so cringeworthy on MY part. But yeah, that was the most awful.

      Liked by 1 person

      1. Hahahahaha. OMG. Craigslist. You didn’t! Hahahahaha. I wonder if craigslist is still going on? Good stuff on their. I once read this RANT on Portland Oregon, it had me in stitches, and the comments were great.


    2. Seriously? Communism?????? I mean, wow. HISTORY, folks, history. How can he be a fan? I know it comes in and out of fashion, but I just did research on China’s civil war and their ‘cultural revolution’ and well, it’s ghastly.

      Well, at least the date was memorable! 😛


  5. Hahahaha, these are hilarious. I don’t think I have any stories like this… I haven’t been asked on many dates. Well, I would meet with guys but we didn’t call it a date. I don’t know xD The only thing I can remember right now is that when I was (very) young and the flirting had progressed to a point where it was obvious there would be kissing that night, I would get so nervous that I would end up puking, ha ha ha! Not ON the guy, obviously, I managed to get to the toilet in time.

    Liked by 1 person

    1. Oh wow. You poor thing. I have heard of folks getting so nervous they puke. I am so lucky that hasn’t happened to me. I’m surprised, but thankful. Ugh. I hope you don’t get that nervous anymore! 😀


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