1. Zero to Sixty in Awkward Seconds
Dinner and a movie had just wrapped up, and there we were, lingering on the doorstep. That's when he tossed the idea of "having some fun" into the mix. My answer? A clear no. He backpedaled with an apology for stepping over the line, and I was all grace, assuring him with a "Hey, I totally understand and it’s okay!"
But here's where things went off-script. My "okay" must have sounded like a green light in his head because, in a flash, his pants hit the floor. I stood there, a mix of shock and disbelief, as I clarified that "okay" was not a secret code for "let's go." The air was thick with awkwardness as he scrambled to get his pants back up.
2. Close Call with a Case of Mistaken Identity
There I was, the fresh-faced newbie of our girl squad, out for a night on the town. We found ourselves at this lakeside bar, sipping margaritas and soaking in the vibe. That's when Mr. Charming stepped in. We hit it off instantly—dancing, laughing, the works. When it was time to leave, I was tempted to stay, lured by his promise of a safe ride home. But our designated driver was having none of it. She herded us out, despite the exchange of numbers and promises of a soon-to-be date.
The morning after, my phone buzzed—a text from him. Butterflies? Oh, yes. He was keen, texting me the next day meant something, right? We planned for dinner, and he offered to pick me up.
His text read, “So, pick you up at the same address?” Confused, I replied, “Same address? What are you talking about.” He shot back, “The house I dropped you off at.” Now I was really puzzled. “You didn’t drop me off?” I texted. His response floored me, “Shut up. We made love in your driveway.”
Hold up. What? “Umm...no, we did not,” I replied, my fingers flying over the phone keys. He insisted, “Yes, we did!” That's when it hit me, and I had to break it to him, “I’m really confused. And I think you are too...but I’m not the girl you went home with last night.”
Just like that, the budding romance fizzled out before it could even bloom. But hey, shoutout to our designated driver—she didn't just get us home safe, she dodged me a bullet without even knowing it.
3. When Fingers Met Pie
Imagine this: there I was, about to dive into the lemony bliss of my lemon meringue pie, when I offered him a taste. He was all "no, thanks," at first, but then, with a glint in his eye, he goes, "Actually that looks good," and—would you believe it—plunged his fingers right into my pie. He licked them off with gusto and, without missing a beat, went in for round two. Yuck doesn't even begin to cover it.
4. Encounters of the Quirky Kind
Back when I was 28 or 29, I found myself in one of those conversations that make you question the whole dating scene. We were barely ten minutes and one drink in when he hit me with, "So do you want kids? Cuz if you do, you don’t want to wait too long. You’re drying up." There I was, drink in hand, utterly baffled. And he, unfazed by my shock, added, "It’s biology. Don’t be mad."
Fast forward to another gem of a meet-up, this time over morning coffee amidst the quiet hum of the early risers. Picture this: every time I answered his questions, he'd erupt with a "Nice!!! High five!!!!" echoing through the calm of the coffee shop. After the fourth or fifth enthusiastic slap, I had to put my foot down. No more high-fiving. It was just too much before my caffeine fix.
5. Table for One, Company for None
There I was, a few months into seeing Mr. Mysterious, who had a knack for keeping me as his best-kept secret. No labels, no flaunting in public, until one evening, he decided to switch it up. We found ourselves out in the open, at a dinner, sitting at the bar. It felt like progress, until his buddies showed up.
Before they could even get a glimpse of us together, he was out of his seat like a shot, joining them as if magnetically pulled. There I sat, sipping my drink, as he texted me from across the room, "Don't come over." So, I became a lone island in a sea of bar chatter, nursing my drink and nibbling at my meal solo until his friends waved their goodbyes.
6. Reunion with a Twist
Once upon a not-so-fine weekend, an old college friend decided to drop by for a visit. She was a brainiac, the kind of intriguing we all remember, and back in our college days, we were both taken. Fast forward, and there we were, reconnecting on Facebook, both single and ready to mingle. She popped the question—did I want to date her? My response? A resounding "hell yes!" I was over the moon, thrilled at the idea.
But let me give you the condensed saga of that visit:
The entire weekend was like a one-woman show of narcissism on parade. She recycled jokes older than the internet itself, passing them off as slices of her life. She boasted about her 'edgelord' antics—like poking fun at cops back in '09 or smuggling Cuban goodies during the embargo days.
Then there was the bar scene. She nearly started World War III with a bouncer over a forgotten ID, despite my place being just a block away. We hung out with some of my closest pals, and no sooner had we said goodbye than she unleashed a tirade against them.
My brother swung by, and after a hearty chat with her, he took off, only for her to spend the rest of the evening gushing about how hot he was. By then, I was just watching the clock, waiting for her departure. My interest had left the building.
When she finally exited stage left, I got a text—a critique of my performance. "You failed all my tests," she said. I laughed at her 'jokes,' didn't play the knight against the bouncer, showed zero interest in her 'passions' (which apparently included bouncer and cop confrontations), and just sat there while she ogled my brother. Oh, and the cherry on top? She didn't even find me attractive.
I didn't bother replying. I just hit the pillow and welcomed sleep's escape.
Months later, at the ungodly hour of 4 AM, she texted again, rehashing her previous review. That's when I let loose, gave her a piece of my mind, and hit 'block' on Facebook. But she wasn't done. She came at me with a barrage of duplicate accounts, hurling threats. Eventually, she tired out, but let me tell you, I didn't just dodge a bullet—I dodged a whole artillery.
7. Dinner with a Side of Ego
My freshman year threw me a curveball when my comp science TA, who seemed like a regular guy, asked me out. I figured, why not? So off we went to this random spot in the city for dinner. He took the liberty of ordering for me, which rubbed me the wrong way, but I let it slide, chalking it up to his familiarity with the menu.
But as the evening unfolded, it was clear this guy was on a solo trip to Narcissist City. He hogged the conversation, constantly reminding me to "pay attention" as if I was in one of his lectures. Then, the topic switched to his ex-fiancé, and he launched into this tirade about how he's done with "entitled white women" and now he's all about "black queens." My comfort level was plummeting fast, and I felt a wave of nausea.
The grand finale? When the check came, he suggested he'd cover it, implying I'd "pay him later" with a not-so-subtle wink. I was speechless, my mind racing for an exit strategy. Feigning a bathroom break, I made my great escape through a side door.
With only two weeks left in the semester, I managed to dodge him until the final. Talk about an unexpected lesson in dodging bullets.
8. Dialogue with a Wall
Chatting with her was like trying to get cozy with a brick wall. Every question I lobbed over was met with a one-word answer or, if the stars aligned, a whole sentence. But that was it—no questions back, no fuel to keep our conversational fire burning.
Then, during one of her bathroom breaks, the older lady at the next table leaned in, conspiratorial and hushed. "I have to say, I really admire your patience. She is a nightmare!" she whispered. And just like that, I felt like I wasn't alone in my silent battle after all.
9. Karaoke Catastrophe
I rolled the dice on a night out with a coworker, a mystery man from the office. Turns out, he was the jackpot of jerks and already plastered by the time I arrived. The "highlight" of the evening? He became that guy, the one who drunkenly heckles the cover band just trying to get through their set.
The lead singer, probably fed up with his antics, threw down a challenge. "I'll give you 10 dollars out of my own pocket if you can tell me this girl's name," he said, pointing at me. And wouldn't you know it, my date's mind went as blank as a fresh sheet of paper, right there with all eyes on us.
Oh, and here's the punchline. The next morning, he had the nerve to text me, "You can try again," as if the night's fiasco was my misstep. As if!
10. Date Night Demolition
Back in the wild web days of 2003, I took the plunge and set up a diner date with someone I met online. I was the early bird, waiting with a mix of nerves and excitement.
She pulled up, and that's when things went south—literally. In a fluster, she mashed the gas instead of the brake, hopped the curb, and introduced her car to a light pole, which gracefully toppled onto a parked van.
Thankfully, no one was hurt, but her cheeks flamed redder than the diner's neon sign. After that grand entrance, I guess the embarrassment was too much. She vanished into the ether, and I never heard from her again.
11. Dental Daze and Dating Hazes
I snagged a girl's number right before a dental showdown with my wisdom teeth. Post-extraction, I was floating on a cloud of dental drugs and, in my haze, I managed to nominate my new acquaintance as my emergency ride home.
The details are fuzzy, but the story goes that she played the knight in shining armor, scooped me up, dealt with my pharmacy run, and tucked me into my apartment where I promptly conked out.
Talk about an unforgettable first date, which, unsurprisingly, was also our last. I can't exactly fault her for not being charmed by my drugged stupor.
To this day, I'm puzzled why the dentist's office would trust a loopy patient to give a reliable contact. Maybe they couldn't get ahold of my usual contacts, but I never dug around for the truth. Some mysteries are better left unsolved.
12. Subway Surprises and Midnight Donuts
Let me tell you about a date that turned into an anthology of 'what not to do'. We matched online, and he was quick to offer a dinner date. Sounded traditional enough, right? He picked me up, and as we drove, he casually asked where I'd like to eat. Indifferent, I said anything was fine, and that's when he made a beeline for Subway. Yes, Subway. And get this—he wasn't even hungry but insisted I grab a bite. So there I was, buying my sandwich while he stood outside like a guard on a smoke break.
By then, my interest had checked out, but curiosity kept me buckled in for the ride—literally. He drove us to a dark, deserted ravine, parked beside what looked like the ghost of a tennis court, and cheerfully suggested, "Okay, you can eat now." There I was, in the dim glow of the car's interior light, wolfing down a sub with the enthusiasm of a kid eating broccoli, all while he watched like it was prime-time entertainment.
I've never been so thankful to see my front door after he finally drove me home. It took me days to fully digest the weirdness of that 'date'. But just when I thought the saga had ended, he reappeared at 2 a.m., unannounced, with a bag of the stalest donuts, and the romantic proposition to "make love" sans protection. Talk about the icing on an already bizarre cake.
13. Third Wheel Woes
Here's a little tale from my 'new in town' chronicles. I was set up for a second date with this guy—no fireworks, but he seemed decent enough. Then, out of the blue, he wanted to bring his buddy along who'd just rolled into town. I'm all about making friends, so I said, "Sure, why not?"
They swung by my place, and we headed out to a dance club. This 'buddy' turned out to be a one-man wrecking crew, dissing everything from my decor to my driving skills. It was clear he wasn't thrilled about my presence, cramping his style with my date.
At the club, he was a nightmare on the dance floor, grinding up on uninterested girls and throwing tantrums when rejected. Meanwhile, my date had vanished into thin air, probably playing wingman to his pal.
An hour in, I'd had it. I tracked down my date and laid it out: leave with me or hitchhike back to your car. He chose the former, with a face like a kid who dropped his ice cream.
Back at my place, my date turned on the charm, apologizing for the Houdini act and swearing his friend would be on his best behavior. Against my better judgment, I let them in. Big mistake. It didn't take long to see that my date, having struck out at the club, was now trying to pawn me off to his friend. I showed them the door, pronto.
The next day, he had the gall to text me, calling me a "baby" and accusing me of a phone charger heist. As if the night hadn't been charged enough.
14. Date Night Down the Drain
Let me take you back to one of my rare forays into the world of dating apps. The setup? A double date at my place, with the possibility of branching off into solo adventures if the vibes were right. But fate had other plans.
The evening took a nosedive when he used my bathroom, and let's just say, he left a lasting impression. A clogged toilet, a mountain of toilet paper, and one mortified date later, my friend stumbled upon the aftermath. Red-faced and without a word, he bolted out of there like his pants were on fire.
The cherry on top? He left his jacket behind in the great escape. Too embarrassed to face me again, he sent a friend on a rescue mission the next day to retrieve it. And just like that, the double date was history, and my toilet had seen more action than my love life.
15. Four's a Crowd
I once met a guy at a networking event who piqued my interest. He suggested Chinese food and a movie, with one tiny prerequisite—I had to meet his four dogs first. He was clear: no love for the dogs, no love at all. Being a dog person, I was game.
I found his place, a mobile home with a yard that screamed 'small dog territory'. But oh, was I wrong. Inside were four large, rambunctious dogs ruling the roost, and the aroma? It was like eau de 'wet dog' times a thousand.
As for the promised dinner and movie? It turned out to be an old-school VHS night in his living room, which quickly escalated to an awkward tango of dodging his advances while the dogs treated us like their personal trampoline.
I noped out of there with a quickness. My clothes took a dive straight into the wash, and my car? It carried the eau de 'dog' for days as a stinky souvenir.
16. Unexpected Licks and Unwanted Promises
There was this guy I bumped into at a local coffee joint. Seemed like a decent fellow, so we grabbed coffee again and eventually decided to try dinner at a bar. That's when things took a turn for the bizarre.
Imagine this: we're at the bar, I'm trying to catch the bartender's eye for another round, and out of nowhere, he goes full canine on me—licks my face from chin to temple. I must've looked like I'd seen a ghost because he started playfully poking me, trying to dial down my 'alarmed' expression.
But wait, it gets weirder. He leans in and whispers, "I'll just poke your sleeping body later"... Yeah, nope. That was my cue to end the date right there.
I escorted him to his car, with a bouncer keeping a watchful eye until I was safely back inside. A few days later, he pops up in my messages, all worried because I hadn't been in touch, and he's talking about swinging by my parents' place to check on me—a place I'd never mentioned, let alone given him the address to.
I laid it out clear for him: one more peep, and the cops would be in the picture. Thankfully, that was the last I heard of Mr. Canine Impersonator.
17. Tapas, Tequila, and 'Terminator
I once went out with a guy who fancied a tapas place for our dinner date. No sooner had we sat down than he started knocking back drinks like there was a prize at the bottom of the glass—three cocktails down in a quarter of an hour. When the waiter came around, hoping to tempt me with a menu, my date shut it down. Dinner, it seemed, was off the table.
The evening spiraled as he blabbered on about his fashion choices, completely oblivious to my dwindling interest. Seeking refuge, I made a beeline for the bathroom, only to be intercepted by the eagle-eyed wait staff. They'd been watching the disaster unfold and were ready to stage my escape.
Their plan? They'd cover for me, telling him I'd bailed while I hid out in the kitchen with 'Alien vs. Predator' for company. After a tense ten-minute wait, they gave me the all-clear—he was gone.
And me? I celebrated my freedom with the real dinner hero: a spicy chicken sandwich from Wendy's.
18. Identity Crisis Over Dinner
I was chatting with this girl who seemed to have a thing for accountants, and lucky me, I was crunching numbers in school. She was over the moon about it, ready to leave her artsy flings in the dust.
We set up a date, and it turns out she comes from a family of high-flying financiers from Singapore. I'm all in, discussing market rivalries with Hong Kong and the like, when she hits me with a question about India's industrial scene. I had to admit I didn't have a clue—I'd never been.
That's when the plot twisted. She couldn't fathom why I hadn't visited "my homeland." I explained I'm as American as apple pie, with roots in Mexico, not India. You should've seen her face—it was like I'd said the sky was falling.
She accused me of pulling her leg, so I pulled out my ID instead, with my unmistakably Spanish surname. That's when the date went south. She demanded I take her home, convinced I was some kind of imposter.
That car ride home? Imagine being stuck in an elevator with someone who's just seen a ghost. Twenty minutes of pure, thick silence.
I dropped her off, and that was it. She ghosted me faster than you can say "identity misunderstanding."
19. Dinner, Dog, and Discomfort
Back in my younger days, when I was a little too shy and a tad too accommodating, I met this seemingly nice guy at a cafe. We planned a date, but he kicked it off on a quirky note by bringing his dog along to the restaurant. Surprise, surprise—we couldn't get in. I thought, "Okay, maybe he thought they'd welcome Fido with open arms."
He mentioned his place was just around the corner and suggested dropping off his canine companion before dinner. I figured I'd wait outside, but nope, he was all about playing the 'good host' and coaxed me into his apartment. There I was, awkwardly standing in a near-stranger's living room, reminding him about our dinner plans until he finally got the hint.
Dinner itself? Let's just say his views were a mix of bizarre and appalling. He had this vendetta against cats and gave me a hard time for wanting to rescue pets. Red flags were popping up like popcorn.
Post-dinner, he insisted on that walk he claimed I'd agreed to. Caught off guard, I went along with it, only to end up back at his apartment for round two. This time, he tried to get cozy, draping his arm around me while firing off a barrage of personal questions. I squirmed, making it clear I wasn't there for cuddles or Q&As.
It took some doing, but I finally got him to take that walk, which was really just my escape route. I bolted for the first train I saw, any train, and made my getaway.
It might not sound like a horror story, but let me tell you, the tears on the train ride home were real. That date left me feeling anything but safe.
20. Bar Hopping with Mr. High Spirits
A decade back, I found myself agreeing to a bar date with a coworker. He had this 'chill guy' vibe, so I thought, why not? I'm no barfly, but he, as it turned out, was a champion drinker.
Fast forward a few hours, and he's a slurring mess. Driving was off the table for him, and with no Uber in sight, I was stranded too. His plan? A wobbly three-block pilgrimage to his place.
I couldn't just shove him into a cab, and since his roommate was another colleague, I figured I'd escort him home and hitch a ride back with the roommate. The route home? Right past the police station.
There, he launched into a full-blown anti-cop monologue, capped off with a sidewalk serenade of his stomach contents. Then, like a toddler mid-tantrum, he plopped down, declaring he couldn't go on.
I left him there in his moment of sidewalk glory, fetched the roommate, and as we circled back, there he was—still marinating in regret. We scooped him up, and he spent the entire drive to my place in the backseat, crying and mumbling apologies.
My roommate wasn't shocked—apparently, Mr. High Spirits was known for his boozy escapades. Needless to say, there was no encore date, and the office air got a tad thicker after that night.
21. Coffee and Conversion Tactics
There I was at 19, just chilling on a bus stop bench, when this knockout of a woman plops down next to me. We strike up a chat, and it's going so well that I muster the guts to ask her out for coffee. She hits me with a 'yes' and seals it with "It's a date." I'm on cloud nine as I hop on my bus.
The day comes, and I walk into the coffee shop to find her there—with a guy parked at her side. No sweat, I think, maybe he's the safety net in case I'm the online weirdo type. I slide into the seat across from her, ready for some get-to-know-you banter, but she cuts straight to the chase.
"So, what do you think about Jesus?" she asks, sliding a pamphlet my way like a secret agent passing intel.
I'm there blinking, thinking this is some kind of quirky icebreaker, until I realize she's dead serious. "I thought this was a date?" I ask, my voice a mix of confusion and the beginning of heartbreak.
Her reply's a gut punch: "I didn't think you'd show up if it wasn't."
I bolted before the tears could start, leaving her, her pamphlet, and her wingman to find another soul to save.
22. Dinner Date Turned Babysitting Gig
I'd been chatting with this guy, and we decided to level up to a dinner date. He was all gentlemanly, offering to pick me up post-work. Then comes his text, "WE'RE on the way," and I'm like, who's 'we'?
Turns out, he's a package deal—single dad with a four-year-old sidekick for the night because his sister bailed. I'm thinking, well, this is not what I signed up for, but let's roll with it.
He's got plans to spruce up after work, so we head to his place. He hops into the shower... and that's the last I hear from him for a solid four hours. Meanwhile, I'm in the living room getting acquainted with his mini-me, who's got a mean right hook to the face—twice.
After setting some ground rules, the kid and I actually hit it off. Who knew? By the time Sleeping Beauty wakes up, we're best buds, and pizza's on the menu instead of the fancy dinner I'd imagined.
I could've bailed while he was out cold, but leaving a kid solo? Not my style. So, after our impromptu pizza party, I Ubered my way home, my date with destiny turning into an unexpected playdate.
23. Myspace Misfire
Back when Myspace was the digital hangout, this guy slides into my DMs, all eager to meet. He's keen on me playing taxi, but hey, I'm not about to let a random dude into my car. Safety first, right? He's not thrilled, but after a bit of digital tug-of-war, we settle on the mall as neutral ground.
I rock up to the mall, and surprise, surprise, he's MIA. I'm hanging around, and when he finally graces me with his presence, he's all, "You've been waiting long?" I'm trying to be Miss Congeniality, so I brush it off with a breezy "nope." And just like that, he calls me a liar.
Okay, odd flex, but maybe he's got a quirky sense of humor? I'm usually quick to shut people down, but I'm trying to be less of a fortress here. So, we wander around, and this guy's got a one-track mind to call me out. Anything I say, I'm either "stupid" or "an idiot" – like when I guess Target's closing time. Spoiler: I was wrong, and he was on it like white on rice.
Enough's enough, right? I bid him goodnight, ditch the date, and next thing I know, he hits me up on Myspace, claiming he's "too spicy" for me. My block button never saw it coming. And that was the grand finale of our Myspace melodrama.
24. Quiz Night with a Twist
Alright, picture this: I match with this girl on a dating app, right? And she hits me with a pop quiz straight out of left field – we're talking life goals, my college GPA, and where I stand on the moral compass. Guess what? I aced it, for better or worse.
Next thing you know, I'm bringing my dogs over to her campus for a stroll, because why not? Things escalate, and we end up getting a little adventurous in my van. But then, plot twist – she's bawling her eyes out on my shoulder, spilling the beans about her brother's fists and her mom's knife-wielding antics.
There we were, just 19 and on our very first date. I really hope she's found her peace since then. She was a sweetheart, just not the kind of drama I was looking to swipe right on as a teen looking for a date.
25. Lost in Translation
Let me take you back to my days in Korea, where I was all about leveling up my Korean skills. I tossed an ad into the online world, hoping to trade my English knowledge for some solid Korean convo. The responses flooded in, and I was out there, coffee shop hopping, on the hunt for the ultimate language exchange buddy.
Enter this one gal who suggested we meet at a café. There she was, the queen of quiet, the empress of awkward. Eye contact? Nope. Korean practice? Hardly. I'd throw some Korean her way, she'd lob back English. I pitched the idea of a Korean-only chat, and she just left it hanging like a bad high five.
It was like trying to tune into a radio station with nothing but static. After a while, I waved the white flag and called it a day. She tagged along to leave, then out of the blue, she's all about grabbing a beer. I dodged that like a pro and tried to make my exit. That's when she hit me with the "When's our next outing?" It clicked – she was on a date, a date so bad it didn't even know it was a date.
But hey, every cloud's got its silver lining, right? That very ad led me to my now-wife. We kicked off on the same note, totally clueless that we were on a date. Fast forward, and here we are, from not-dates to soulmates.
25. First Date Fiasco
Picture this: my very first dive into the online dating pool, and I'm all set to meet this lady at a cozy little café. I'm there, fifteen minutes of eager anticipation under my belt, when my phone buzzes. She's running late, locked out of her place. "No sweat," I say, all understanding and chill.
But then, the clock's hands are doing laps, and I'm still solo, nursing a coffee an hour past our date time. Just as I'm about to flag down a barista for a sympathy refill, she breezes in. I'm about to wave when—ring, ring—she's on the phone, giving me a verbal smackdown for playing hide and seek.
Turns out, she's the real deal from her profile—minus the full-body shots. There she is, decked out in the universal uniform of 'I can't even': sweatpants and sweatshirt. But hey, fashion's the least of my worries because she's about to unload her life's drama on me like I'm the season finale of a soap opera.
"Want to know how my day's been?" she asks. Curiosity killed the cat, but I'm more of a dog person, so I say, "Hit me with it." And boy, does she. Fired from her job because of a conspiracy, scammed out of her credit card details, fresh from a relationship that was all fists and fury, and her sister's ditching the family for the Big Apple dreams.
And the cherry on top? She's been booted from school over some wild assassination plot she's apparently the star of. "People are always plotting to get me," she says. And there I am, stuck in my seat, frozen like a deer in the most awkward headlights, making small talk that's about as smooth as sandpaper.
An hour later, I'm still there, wondering if this is what all online dates are like, or if I've just hit some kind of jackpot.
27. Valentine's Day Vanishing Act
Imagine being 15, all butterflies and blushes, gearing up for your very first date. Valentine's Day, no less! This guy and I had been texting up a storm for three whole weeks, and even though we hailed from different schools, we managed to meet up a couple of times.
There I was, on the big day, showing up half an hour early, heart pounding, mind racing with all the possibilities. Thirty minutes turned into an hour, and I sent him a couple of texts, just trying to get a bead on him. Two hours ticked by, and he's MIA. I even tried calling, but nope, the guy's off the grid. I trudged home with tears in my eyes, the day's romance fizzling out like a dud firework.
Later that night, he rings me up with a story about being hijacked by his buddy for some urgent project. I mean, sure, stuff happens, right? But what really got my goat was the radio silence. A simple text, a heads-up, that's all it would've taken. Instead, I got stood up and left out in the cold. And just like that, my excitement for dating turned into a big, fat caution sign.
28. Slip, Slide, and Awkward Rides
Picture this: I'm at this cozy little hotspot that's absolutely buzzing with people. It's so packed that my date and I end up sharing a booth with another couple. And what does my date do? Starts flirting with the other guy right across the table. His date and I exchange "Is this really happening?" looks while our dates are lost in their own world.
After we bail on that disaster, the universe decides to throw in a plot twist—it's snowing like a winter wonderland out there. My date, who's not exactly on solid footing, takes a tumble and suddenly, I'm in knight-in-shining-armor mode, hauling her down the snowy streets back to her place.
Then, out of nowhere, she makes a beeline for this SUV crawling through the snow, pounding on the window for a ride. The driver peels out faster than you can say 'awkward.' So there I am, carrying her home, wondering if she needs an ER, offering to call a cab since my car was a no-show. But she's all over the place, one second yelling for me to scram, the next begging me not to leave.
I scribble down my digits, tell her to ring me if she needs hospital time, and finally make my great escape from the rollercoaster of her mood swings.
Fast forward a couple of weeks, I'm out grabbing beers with my roommate, and guess who's there? Yep, my date from that night, sporting a cast that's practically a leg trophy, shouting about her broken leg. I wish her a speedy recovery, and my roommate and I make a swift exit. And in case you're wondering, nope, I didn't end up with the girl from the other couple either.
29. Cheetos, Chaperones, and City Tours
Let me take you back to this one time when I was supposed to meet this girl from another city. She was rolling in with her brother, who, she assured me, would hit the road soon because he had a busy day. Well, that was the plan anyway.
Turns out, they were pretty much strangers to my city and needed someone to show them around. No sweat, I thought, playing tour guide is kind of my thing. But her brother, well, he wasn't exactly my fan club president, if you catch my drift. So, I kept it cool, stayed in my lane, but the dude stuck around like he was glued to us.
Fast forward to the grand finale of this walking tour, she leans in for a kiss—mind you, we're talking full-on Cheetos aftermath here—and her brother puffs up like a Thanksgiving Day parade balloon, "YO GET AWAY FROM MY SISTER YOU CREEPY FREAK." Talk about mixed signals, right? I noped out of there faster than you can say 'awkward.'
We hung out a few more times, but let's just say it didn't turn into a fairy tale. That day was one for the books.
Oh, and remember the girl with the leg cast? Ran into her a while later when I was out with my roommate. She's there, waving her cast around like a flag, announcing her broken leg to the world. I wished her well, and my roommate and I made a quick exit stage left. And just for the record, no, I didn't end up with the other girl from the booth either. What a day, huh?
30. Plot Twists and Ice Cream Scoops
Alright, picture this: I'm on a second date with a guy who had all the makings of Mr. Right—until the plot thickened. Out of the blue, he starts sharing his writing with me. As a fellow scribe, I was all ears, but then he dove into this story about women in the slave trade. And let me tell you, it was a deep dive.
Then he hit me with another tale, thank goodness the details have slipped my mind, but it was another heavy one about women suffering. I couldn't help but ask him why he was drawn to such dark themes. "Just for fun," he said. Fun? That sent my weird-o-meter off the charts, and just like that, our story ended—no sequel in sight.
Now, fast forward to a different chapter. I'm on an ice cream date with another guy, and we're chatting over our cones when suddenly, the convo takes a nosedive into his mental health woes. It went on for hours. I mean, I felt for the guy—he clearly needed a listening ear, but a first date isn't exactly the place for unpacking baggage. He was battling demons that sprinkles and syrup couldn't sweeten.
And here's the kicker: both of these dudes were "writers." That's right. Since then, I've put a full stop on dating other writers. It's just too much of a plot twist for my taste.
31. Dinner and a Side of Mama Drama
Check this out: I'm at this cozy Italian spot with a guy I just met. We're browsing the menu when his phone rings. He picks up and starts this casual convo, and then, out of nowhere, he drops this bomb: "Mom, I know, I ordered the cheapest thing on the menu. Mom! I'm here with my girlfriend. I'll tell you how much the bill was afterward."
Hold up. Rewind. First off, this was date numero uno, and I was definitely not the girlfriend. And secondly, this dude's mom was like his personal finance hawk—so much that she'd call during dinner to audit his pasta purchases. Talk about a mood killer.
I gave it one more shot, just to see if he was truly as oddball as he seemed. Spoiler alert: he was. And that was the last supper for us.
32. Lunch with a Side of Judgment
Picture this: I'm sitting across from her at our favorite lunch spot, just chatting away. Then she hits me with the "What church do you go to?" question. I casually mention I'm an atheist, and man, did that set her off. She launches into this tirade about how my life's got no value without God or Heaven and that I might as well not exist.
Now, this is a joint where everybody knows my name, so I did what any regular would do. I grabbed my plate, found a new spot to enjoy my meal in peace, and gave the waitress a heads-up that we'd be going Dutch on the bill.
33. Hydration Overload on Date Number One
Alright, let me take you back to the days of high school, where my dating game was... let's just say, less than stellar. It was the first date I'd ever been on, and boy, was I a bundle of nerves.
I decided to impress her with a dinner at what I thought was a swanky spot. Every time there was a lull in the conversation, which, trust me, was often, I'd take a massive gulp of water. You know, to avoid those awkward silences. By the end of dinner, I'd downed maybe seven glasses of water. Rookie mistake.
Next up, movie time. We snagged seats in the back row, smack in the middle, prime real estate, right? The theater was buzzing, and the movie had everyone glued to their seats. Everyone except me. Because, well, nature was calling. Loudly. I must've shuffled past that entire row of people to hit the restroom at least FIVE times.
The guy next to me? He couldn't decide whether to be annoyed or amused. I could hear his stifled laughs every time I scooted by. Needless to say, she didn't sign up for a sequel to that date. I can't help but wonder what went through her head as she watched me do my awkward 'excuse me' dance down the row, over and over.
34. Caught in the F1 Fanatic's Lair
Let me tell you about the time I ended up at this guy's place, and he was all about Formula One. I mean, I couldn't squeeze a word in edgewise. This dude was on a roll, giving me the entire history of F1, diving into drivers, engines, and chassis design changes. He even whipped out model cars to point out different parts – it was like a lecture I never signed up for.
There I was, stuck in the most one-sided date of my life, practically grooming his cat into baldness out of sheer frustration. It was like being held captive in a racing fanatic's personal museum.
Desperate times called for desperate measures. I had my co-worker ring me up – picture this – at 8 PM, during a snowstorm, while I'm an hour away from home. He's on the other end, spinning this yarn about an ER crisis only I, the "boss," could handle. We even staged a little argument over the phone for that touch of authenticity.
Thank goodness, the ruse worked. I hightailed it out of there, blocked Mr. F1 for good, and never looked back. Talk about a great escape!
35. Mr. Moneybags and the Pizza Saga
Let me paint you a picture of this one date I had. I wasn't exactly head over heels for the guy from the get-go, but he had this nice-guy vibe, so I thought, why not? Big mistake. The guy turned out to be a walking, talking billboard for his bank account, bragging about his cash flow the entire time.
So there we were, sharing a pizza. I nibbled on a single slice while he demolished six. Then, the bill arrived, and Mr. Big Bucks suddenly turned all about equality, suggesting we split it down the middle "because that's how things work these days." Talk about mixed signals.
The cherry on top? He leaned in for a kiss when he dropped me off, and whoa, his breath was like a blast from a garbage can. I could've sworn he snacked on roadkill before our date.
And just like that, I was out. Blocked him and left that date in the dust.
36. Crash Landing on Crushville
Let me tell you about this one time I was on a date with a guy I'd been crushing on forever. There I was, all happy and bubbly, thinking, "This is it, this is the moment!" We were just chilling, munching on some food, and then we got to talking about this mutual friend of ours. She's pretty cool, studying at a uni just a stone's throw away, and we both agreed on that.
But then, out of the blue, he whips out his phone and dials her up, inviting her to crash our dinner. And just like that, I felt like I'd been hit by a truck of rejection. Time might as well have stood still because, in that moment, I felt like the most unattractive and unwanted girl on the planet.
37. Dinner and a Side of Shenanigans
Okay, picture this: I met a guy on Plenty of Fish, and we decided to hit up O’Charleys for our first face-to-face. Dinner was... interesting. He was driving the waiter up the wall, and I should've taken that as my cue to bail. But nope, I hopped into his car after dinner. Next thing I know, we're heading towards this super sketchy warehouse area, and he's got this look like he's planning a steamy car rendezvous.
But wait, it gets weirder. We didn't end up at makeout point. Instead, he pulls into this elderly assisted living complex, rambling about how his buddy's looking to move in. We're talking full tour mode here. He finds this garden, probably tended by the residents, and starts munching on the veggies like it's his own personal buffet.
There I am, thinking he's done this before, and I start playing detective with his phone number right there in the middle of veggie heist central. And what do I find? The guy's freshly hitched and has a rap sheet of domestic violence longer than a CVS receipt. Spoiler alert: I made it out and lived to tell this wacky tale.
38. Lunch Date Turned Soul-Saving Session
Alright, let me set the scene: there I was, a gal all gussied up for what was a pretty big deal for me – my first ever date with another girl. I'm talking full-on butterflies and everything, trying to look my absolute cutest because, hey, I don't usually do the whole dress-up thing.
We picked this cozy little spot for lunch, a place where I thought we'd swap stories and share a few laughs. But no sooner had we sat down, she whips out a Bible like it's a menu and starts preaching about the sins of homosexuality. There I was, all dolled up, and she's on a mission to 'save my soul.' Talk about a plot twist, huh?
39. Swipe Right for a Free Meal? Think Again!
Picture this: I'm there at the restaurant, right on time, and she rolls in fashionably late. For the next quarter of an hour, it's just me and the top of her head, because she's glued to her phone. I'm getting the full range of one-word wonders – "Yep," "Totally," you name it.
The waiter pops over, and suddenly she's all about the shots. "Should we start with two or three appetizers?" she asks, eyes not leaving her screen. "Thinking about dessert?" Meanwhile, I'm just nursing a beer and giving the menu a casual glance.
No sooner has the waiter left than she's back to her digital world, tossing out those one-word gems. Then she goes all out, ordering a feast fit for a queen – three appetizers, a shot, and another margarita. Mind you, she's barely settled in.
After about five minutes of this charade, I excuse myself to the 'bathroom.' Instead, I find our waiter, cover my beer and his tip, and let him know she's got her meal covered. I slip out, hoping to throw a wrench in her little Tinder dinner scheme. If I spoiled her day? Well, I can't say I'm not a little pleased. She was clearly on the hunt for a free feast, and that's just not how I roll.
40. Zero to "Wife" in Five Minutes Flat
Check this out: I walk in, and the guy's already on the phone, chatting up a storm about his "new wife" – that's me, apparently. We'd barely exchanged hellos, and there I was, upgraded to spouse status in his family chat. I stuck around for a drink or two, trying to be nice. I was fresh in town, after all, and figured, why not give the guy a shot?
He's all excited, wanting to show me his new pad, talking it up like it's some kind of real estate showcase. Me, being the newbie that I was, too polite for my own good, I went along. Big mistake.
The moment we're inside, he goes full octopus on me, tongue and all. I'm talking zero to panic in a heartbeat. I managed to push him off, sprint to the door, and I'm out of there, racing to the safety of the train station.
And would you believe it? He had the nerve to keep calling, as if we were going to have a round two. Nope, not a chance, buddy.
41. Dating by the Book... Literally 7
Alright, picture this: I'm on a Tinder date a while back, and this girl walks in, right? We're just getting settled at our table when she whips out a clipboard. Yes, a clipboard. And not just any clipboard – this thing's got a full-on checklist.
She dives right in: "Do you want kids?" "How many?" "What's your political jam, and why?" She's grilling me about my major, the starting salary stats, and get this – if I'd be cool being Mr. Mom if she's raking in the big bucks.
There must've been like 30 questions, and after the interrogation, she just tucks the clipboard away and flips back to chill mode like nothing happened. When I'm like, "What's up with the quiz show?" she says it's her strategy to scope out if we're on the same life page.
I played along, finished the date, but man, I just couldn't shake off the whole clipboard interview vibe.
42. Movie Night with a Side of Background Check
Let me take you back to when I was 18. I had this simple plan: ask a girl out to the drive-in, along with a couple of friends. But her dad was having none of it. Instead, he invites me over to their place for a movie night. Random pick from the movie stack – thank goodness it was PG, because her dad's eyes were like lie detectors.
Now, her dad was a fireman, and he had this buddy from the police department. Before I knew it, I was getting a background check as if I was applying for a top-secret government job. Meanwhile, I'm sitting there getting the classic "What are your intentions with my daughter?" interrogation.
Turns out, I'm clean as a whistle. But the evening's vibe? Awkward with a capital A. We're on the couch, miles apart, under the watchful eye of a wall-mounted arsenal. Dad's lurking in the next room, probably with his ear against the wall.
Movie wraps up, I do the polite 'good night' routine, and I'm out. Still made it to the drive-in with the gang. As for a second date? Yeah, no. One background check per customer.
43. Dinner, Pink Lights, and a Plumbing Disaster
Picture this: it's the turn of the millennium, AOL is the gatekeeper of online romance, and there I am, fresh out of a marriage and about as seasoned in the dating game as a newborn. I meet this guy online, we hit it off, and decide to have dinner. Dinner goes well, and he invites me over. Now, I'm green in the ways of dating, but I figure, why not?
We get to his place, and it's decent, but the guy's living room is giving off strong 'bachelor pad meets yard sale' vibes. We're sitting on the floor, and there's this lamp that's casting a pink glow. Turns out, it's a family heirloom from his family's funeral home business. Yeah, the pink light is for making the dearly departed look more... lively.
Nature calls, and I head to the bathroom. Let's just say things go south, and I'm left staring at a clogged toilet with no plunger in sight. Panic sets in. I'm considering all options, including a new identity in a foreign country.
But no, I do the only thing my mortified self can think of. I waltz back, chat for a few more, say my goodbyes, and leave without a word of the disaster I've left behind. He calls later, probably before the grand discovery, to check if I made it to the highway. Little did he know...
Needless to say, that was the end of that. I still cringe thinking about it. Clogged toilets and potential love interests? Not the best mix.
44. Sideways Glances and Conspiracy Theories
Alright, let me take you on a little journey. I met this guy online, and he's from a small town about a forty-minute drive from my mid-sized city life. He suggests I come to him, and despite my reservations about the not-so-bustling town and its less-than-progressive views, I agree.
Now, this date, it's one for the books. The guy's got a thing for conspiracy theories. And I'm not just talking about who shot JR, but full-blown 'every celebrity you know is in the Illuminati' level stuff. But here's the kicker – the entire time, he's giving me the cold shoulder, literally. He's angled at 45 degrees, and I'm catching nothing but his profile view.
We're at dinner, and he's practically a contortionist in his chair, making sure I'm in his peripheral at best. I try to play it cool, you know, casually step around to face him, and what does he do? He just swivels away, another 45 degrees, like we're in some weird, slow-motion chase scene.
And that, my friends, is the story of my sideways date with the conspiracy theorist.
45. The Not-So-Funhouse Mirror
Let me tell you about this one time I went on a date with a girl I'd met online. She was a knockout, and we'd been vibing over text, so I was pretty stoked. We hit up this cozy little bar, and she's got this idea to play a people-watching game where we invent stories about the other patrons. I'm all in because hey, it's like the game I play with my buddies on the train, right?
But oh boy, did it go south. This game, which should've been a laugh, turned into a roast session. She wasn't just making up stories; she was tearing these strangers to shreds. Take this one dude at the bar, probably just chilling or waiting for a friend, but according to her, he's this friendless loser who's absolutely miserable.
Talk about a vibe killer. It was like she was unloading a truckload of baggage onto these unsuspecting bar-goers. That was it for me. I mean, how could I line up a second date when the first one left such a bitter taste? Nope, I couldn't picture it.