Tales from the Tangled Trail

Tag: datingdisasters

  • 101 Disastrous Dates in America : Part Two

    After the date with Matt-the-Rat — and seeing that I was clearly one emotional wobble away from adopting thirty-seven cats — my cousin Jackie invited me to spend the weekend at her house. I grabbed the offer like it was the last lifeboat off the Titanic of my love life.

    Jackie, spoke my language – we shared an appetite for the party lifestyle. She enjoyed a cheeky drink once the kids were in bed, and — bless her nicotine-loving heart — she smoked. To me, this was basically an international sign for “safe space.”

    Over the weekend, I poured my soul out to Jackie. I told her everything: how Matt the Rat was a definite no-go, how there was no way I could marry him without entering the Witness Protection Program, and how guilty I felt for letting Jennifer down after she’d basically rearranged her entire life to make space for me. (Probably not realizing how long it would take to get rid of me. Honestly, at that point, I wasn’t even sure how long it would take to get rid of me.)

    Jackie, being the ultimate take-charge kind of girl, decided it was time to switch gears. She was going to take over the matchmaking. A deal was struck: Jackie had two kids, her youngest almost a year old, and in exchange for a place to stay, I’d look after the baby while she went back to school to get her teaching degree. The arrangement was perfect — no kids to chauffeur around, a spare room downstairs where her mom used to stay, and best of all, zero pressure to marry anyone named after a rodent.

    I felt pure, unfiltered relief. I loved Jennifer deeply — she was like the sister I wished I’d been born with — but I was battling a war inside myself. As much as I admired her faith and the life she was building, I couldn’t seem to let go of my party-girl lifestyle. That was where I’d built my identity, and without it, I wasn’t sure who I even was.

    Every time I went to church, I felt like a fraud. Sitting there, I couldn’t shake the weight of my past: all the bad choices, all the mistakes, all the nights I’d rather forget. Instead of feeling redeemed, I just felt like a walking contradiction — singing hymns on Sunday and still clinging to the girl who lived for Friday nights.

    And then there was the shame. I didn’t feel worthy of a good man — not one who was kind, steady, and actually respectable. But here’s the kicker: even in my mess, I was too shallow to settle for an “ugly” decent man. I wanted my cake, my champagne, and my handsome dreamboat too.

    Life at Jackie’s was definitely “livelier”. She made me her personal husband-hunting project, and I — because I was busy picturing the grand entrance of my future dream man — went along with it. Within days, she’d identified her prime candidate: a bachelor named Larry who lived alone on the corner of her street.

    According to Jackie, Larry jogged past her house at the same time every morning. So there I was, for the next few mornings, “casually” stationed at the window, baby on hip, pretending I just happened to be there, when in reality I was trying to look both available and not at all like a woman waiting for a man she’d never met to run by.

    Larry wasn’t bad-looking, but he wasn’t exactly the swoon-worthy dreamboat I’d imagined sweeping me off my feet in a slow-motion, hair-blowing, movie-scene kind of way. He was clearly a few years older, but he was all there was.

    Jackie wasn’t about to let this opportunity jog past her — literally. One day, after spotting him trotting down the road, she marched outside like a woman on a mission, struck up a conversation with Larry, and before I knew it, I’d been lassoed into the small talk.

    Somehow, the conversation meandered to movies, and I casually mentioned that one of my all-time favorites was The Bridges of Madison County. The very next day, a mysterious gift bag appeared at the front door. Inside? A DVD of The Bridges of Madison County and a box of chocolates.

    Jackie was beside herself — convinced that wedding bells were practically echoing down the street. Me? Not so much. My main concern was that other people might take one look at Larry and think, Oh, honey… you could have done better.

    One day, while Jackie was off at college, there was a knock at the door. Standing there was Larry, smiling confidently, and before I knew it he’d asked me out to dinner. I accepted with a nervous smile — though inside my stomach was doing somersaults with a ball of lead. It wasn’t excitement; it was the heavy weight of compromise, sitting there like a bad meatball I couldn’t digest.

    Jackie, of course, was ecstatic. If it were up to her, I’d have been engaged by the following Tuesday. With great pomp and ceremony, she paraded me around her bedroom, determined to “tart me up” for the evening. She fluffed my hair, picked out an outfit, and practically hummed the wedding march while applying my lipstick.

    When the doorbell finally rang, Jackie’s husband answered, ushering Larry inside. It was mid-summer — the kind of humid, sticky heat where you pray deodorant will hold the line. And in walked Larry… wearing a black turtleneck. A black turtleneck. Paired with pants so tight they gave me circulation issues just looking at them. I didn’t know whether to offer him dinner or a crowbar to peel himself out of that outfit.

    Jackie shot me a wide-eyed grin that screamed, He’s perfect! Meanwhile, all I could think was, Oh Lord, I’m about to spend the evening with a man dressed like an off-duty cat burglar.

    He politely declined a drink — which was honestly a relief, because I just wanted to get out of there and not spend the evening watching Jackie and her husband silently debate the deeper meaning of his… let’s say, “interesting” wardrobe choice.

    He ushered me into his very nice car (point in his favor) and drove us to an equally nice restaurant (another point in his favor). Honestly, the tally sheet was looking good. The ambience was lovely, the food smelled divine, the lighting was soft and flattering — it was all perfect. Perfect, that is, except for the glaring detail that I would’ve preferred being at home in sweatpants watching reruns of Friends.

    When it came time to order, my inner foodie perked up. If I was going to endure this, I may as well enjoy it. I went big: a gorgeous, slightly pricey seafood dish. Totally worth it.

    Then Larry said the unthinkable.
    “I’ll have… the salad.”

    A salad. A salad.

    I felt my face flush bright pink, like I’d just been caught sneaking a swig from the communion cup. Who orders a salad on a dinner date? Suddenly I wasn’t sure who the girl on this date was — me, or Mr. Turtleneck-Tight-Pants-Salad-Orderer.

    After dinner — which I barely touched because I was hyper-aware of every shrimp sliding down my throat while he daintily crunched away on lettuce — I declined dessert. Honestly, I prayed he wouldn’t order anything either, because at that point I just wanted to go home and pretend the whole evening had been a bad dream.

    Instead, he hit me with, “Would you like to come in for a nightcap?”

    Now, here’s the thing: I had walked past his house countless times on my walks, so I was curious to see the inside. But I also worried that stepping foot over his threshold might give him the wrong idea — like I was more interested than I actually was. Still, I couldn’t exactly rush home and tell Jackie, “Yeah, it was awful, I bailed.” So, against my better judgment, I said yes.

    His house turned out to be extremely neat, decorated in what I can only call “early bachelor minimalism.” Maybe he just wasn’t a man for fuss, or maybe he’d never met a throw pillow in his life. Either way, the place was tidy… almost suspiciously tidy.

    There was only one couch — no armchairs, no second option. Which meant, of course, I had no choice but to sit there. He poured us both a glass of wine, then came and sat down way too close. The kind of close where I suddenly wondered if personal space was a concept that had somehow skipped him entirely. But what was I supposed to do? Scoot onto the coffee table?

    Trying to fill the silence, I asked why he’d never married. That cracked open a long, sad story — the details of which I’ve completely forgotten. What I do remember is that it was bleak. The man was in his early forties (ancient, to me at the time) with no wife, no kids, and nothing but that lone couch for company.

    Now, Jackie would have considered this the jackpot: no ex-wife drama, no stepkids to wrangle, and no competition for his inheritance. In her mind, he was basically husband gold. Me? I sat there nursing my wine, desperately trying to squint hard enough to see the “potential” she was so convinced was there.

    The evening ended abruptly when he offered me a second glass of wine. I declined, and that’s when I saw it — the unmistakable lean-in. He was going for a kiss. I sprang off that couch so fast you’d think the upholstery was on fire. “Oh, I’m just so tired after looking after the baby all day,” I blurted, which was a complete lie but the only excuse I could conjure up to escape the impending lip-lock.

    To his credit, he didn’t push it. He walked me back home and gave me a polite peck on the cheek. That, I could deal with. But the whole thing was so painfully awkward I wanted to melt straight into the sidewalk.

    The very next day, there he was at the door again, asking if I’d like to come over for lunch and movies on Sunday. With Jackie and Dean both standing within earshot, I had zero chance of wriggling out of it gracefully. So I smiled, nodded, and accepted my fate.

    Sunday arrived, and Larry pulled out all the stops. He put on The Bridges of Madison County, handed me a glass of wine, and set out popcorn. Honestly, if you’d written this into a romance novel, it would’ve been the dream date. Every box was ticked — food, wine, movie, cozy setup.

    But there was just one tiny problem: I felt nothing. Absolutely no attraction. Zilch. Nada. I should’ve been floating in dating heaven, but instead I was mentally checking how long the movie was and wondering if it would be rude to fake a migraine. Even I couldn’t understand myself. Here was a man doing all the right things, and I was still as emotionally engaged as a potted plant.

    I knew the kiss was coming. It was only a matter of time, and I resigned myself to just letting it happen. Part of me even wondered if, by some miracle, his kiss might flip a switch in me — that maybe sparks would fly, violins would swell, and I’d suddenly feel the attraction everyone else thought I should.

    Well… nothing changed. At all. His kiss wasn’t terrible, but it wasn’t good either. It was just… awkward. Awkward and awful. And to make matters worse, he sensed how stiff I’d gone, like I was bracing for a flu shot.

    “What are you thinking?” he asked.

    Oh dear. The dreaded question. By then I knew he’d thrown in the towel, and my guilt poured in like a tidal wave. I felt terrible for him — and, honestly, even worse for me. Here was a really decent guy, kind and thoughtful, and I couldn’t muster a single flicker of attraction. I kept wishing I could just get over myself and make it work.

    But the truth was, it really wasn’t him. It WAS me. He deserved a woman who didn’t come with the suitcase full of issues I was lugging around. In the end, I actually did him a favor.

    Of course, that didn’t make it any less awkward. I still had to adjust my walking route so I wouldn’t pass his house every day. Nothing like rerouting your cardio to avoid an ex-almost-something.

  • 101 Disastrous Dates in America : Part One

    Following my nightmare odyssey from Miami to Tampa (a trip that still haunts me like a bad country song), the rest of the holiday was—miracle of miracles—incident-free. Well… almost.

    The only hiccup was that I had to share a hotel room with my parents and my aunt. All three of them snore—not just regular snoring, but competitive, synchronized snoring. I’m talking the kind of deep, guttural, freight-train-meets-blender sound that could make an insomniac weep.

    The Snore Games: Midnight Bathtub Retreat
    When sharing a room means sleeping with the snore symphony.

    Most nights, I’d last maybe ten minutes in the bed I was sharing with my aunt before my sanity started to fray. Then, in a dramatic midnight exodus, I’d grab my blanket and relocate to the bathtub. Yes—the actual bathtub. With the bathroom door shut for extra soundproofing. I’d curl up like a slightly disgruntled cat, convincing myself it was “cozy” while quietly mourning my spine.

    Meet the Hallmark Cousins—and Their Perfect Lives
    Why jealousy is a powerful motivator.

    When the trip wrapped up, I had planned to spend a few days with my cousins before flying home. This was my first time meeting their husbands, and I’ll admit, I had a moment of pure, green-eyed envy. They were both so lovely, so warm, so disgustingly functional. Their lives seemed straight out of a Hallmark movie—handsome husbands, two kids each, cute houses, family photos where no one blinked.

    My cousin Jennifer, a kind-hearted angel who apparently moonlights as a matchmaker, listened to my tales of tragic dating and had an idea.
    “Why don’t you move to Florida?” she suggested. “Come to our church. That’s how both of us met our husbands. You could meet a nice guy here too!”

    It was like she had handed me a golden ticket to the Love Lottery. Their lives looked so perfect, I was ready to buy into the dream wholesale. When I got home and told my mom about this “Operation: Husband Hunt,” she practically started packing my bags for me.

    By Monday morning, I was in the office handing in my resignation, smiling like a woman about to be swept into a Nicholas Sparks novel. My mom, fully invested in my romantic quest, bought me a ticket back to Florida. And just a few weeks later, I boarded that plane—determined to find myself a husband in America.

    Because honestly, what could possibly go wrong?

    Saint Jennifer’s House: A Bedroom Shuffle for Love
    Making room for romance, one child at a time.

    The plan was for me to stay with Jennifer, who, bless her saintly heart, rearranged her entire household to make room for me. She even moved one child into the other’s bedroom—a small but noble sacrifice in the name of my grand romantic mission. Honestly, it felt like the kind of selfless act that should be commemorated with a plaque.

    The Singles Sunday School Illusion
    Where men lurk… or don’t.

    I arrived brimming with anticipation, fully convinced I’d meet the man of my dreams at their church. According to Jennifer, the real magic didn’t happen during the Sunday service itself—oh no—it happened afterward, in the Singles Sunday School class. That’s where all the eligible men supposedly lurked, waiting to be swept away by a God-fearing woman with excellent hair.

    At no point in this elaborate plan did I actually consult God. I simply assumed He’d be on board. I mean, why wouldn’t He? I was attempting to marry a wholesome Christian man—surely this was His department. Never mind the fact that my lifestyle up to this point had been a little more… spirited… than saintly. But if Jennifer, a proper Baptist girl, could find love at church, then clearly I could too.

    Culture Shock: Quitting Smoking and Living Like a Raccoon
    The price of American independence.

    There was, however, one immediate sacrifice required: I had to quit smoking. I figured it would be easy—after all, I was giving up a vice in exchange for a husband. Seemed like a fair trade. Spoiler: it was not easy. It was pure, unfiltered agony. Nearly as agonizing as my second, unexpected culture shock—apparently, in America, you clean up after yourself. No domestic worker magically appearing to pick up your clothes, make your bed, and bring you tea. You either stayed tidy or slowly descended into living like a feral raccoon. This was not in my romance plan.

    Invisible at Church: The Unseen Outsider
    When your social skills don’t translate.

    Still, I had bigger things to focus on—like Sunday. My first church service arrived, and off we went. Afterward, we headed to the much-hyped Singles Sunday School class, where, presumably, I’d be wooed by a charming, Bible-quoting bachelor. Instead, I found myself standing in a room full of strangers who somehow made me feel even stranger. No amount of strategic makeup or stylish outfits could hide the fact that I was an outsider—a slightly sinful stray who had wandered into the fold.

    But I didn’t give up. Week two rolled around, and Jennifer handed me her car so I could drive myself to church. On the wrong side of the road. I figured my ability to survive American traffic was at least an attractive quality in a mate. But week after week, the same thing happened—nothing. No smiles, no coffee invites, no “Hey, let’s do a Bible study together.” It was as if I’d been issued an invisibility cloak at the door.

    The only thing I was attracting was mild jet lag and a creeping sense of doom.

    I’m not sure what I’d been expecting. Maybe some breathtakingly handsome man—think my cousin Jackie’s husband, but single—would spot me across the room, be struck by divine lightning, and immediately drop to one knee in the fellowship hall. Instead, I was just another anonymous face in a sea of well-adjusted, church-going people who could somehow smell that I was wildly out of my element.

    And yet, I persisted. I mean, I hadn’t quit smoking and house-trained myself for nothing.

    After several weeks of coming home from church with exactly zero romantic prospects, Jennifer began to… gently apply pressure. Nothing too overt, just the occasional “helpful” suggestion, a few pointed questions, and the odd reminder that maybe—just maybe—I could be putting in a bit more effort.

    The problem? I suffered from a chronic case of Cinderella Syndrome, courtesy of Hollywood. In my head, I wasn’t supposed to look like I was hunting for a husband. No, my knight in shining armor was supposed to just appear—preferably on horseback—fall instantly in love, and sweep me off to our happily-ever-after. Instead, all I was getting was Jennifer’s unsubtle hints that perhaps I needed to make myself a bit more… noticeable.

    So Sunday mornings went from being filled with hopeful anticipation to being filled with dread. How exactly was I supposed to stand out in a sea of polished, wholesome singles? Wear a tiara? Trip in front of the communion table?

    And then—finally—luck struck. Or divine intervention. Or maybe just a random act of social bravery.

    Snack Table Salvation
    How desperation can make rodents seem charming.

    That Sunday, in a desperate bid to look approachable, I forced myself to grab something from the snack table instead of making my usual quick exit. I even sat down to eat, pretending I wasn’t silently calculating how quickly I could leave.

    That’s when it happened.

    He approached.

    Let’s call him Matt.

    My first impression? Matt looked like a rat.

    I know, I know—terrible. But hear me out. He had jet-black hair, a long, skinny face, a very prominent (read: enormous) pointy nose, and a small mouth. If you’d told me he moonlighted as a villain’s sidekick in a Disney movie, I would have believed you.

    Still, credit where credit’s due—he was the first man in weeks to actually approach me, and for that alone, I felt obligated to at least pretend to be interested.

    As expected, our conversation opened with my accent. This was my standard church interaction:
    “Oh wow, where are you from?”
    Followed by the usual Greatest Hits: “Do you ride elephants? Is it safe? Do you know Charlize Theron?”

    I played along, but I was also subtly scanning the room, just in case a less rodent-esque man was lurking nearby, waiting for his turn. Alas, the crowd seemed almost aggressively indifferent to my existence, so I resigned myself to giving Matt the Rat my undivided attention.

    After a while, he glanced at his watch and said he had to go—but plot twist—he invited me to a cookout one of the girls from the Sunday School class was hosting.

    The Cookout Invitation
    When a number exchange feels like signing a treaty.

    A social event! My inner Cinderella immediately perked up. Surely this was the perfect opportunity to expand my options, get some much-needed exposure to other men, and maybe—just maybe—meet someone who didn’t look like he could gnaw through drywall.

    Then came the moment of truth—Matt asked for my number so he could send me the details.

    I hesitated.

    This was clearly a man with a plan. And while I wasn’t exactly swooning, I figured accepting the invite might improve my odds. A cookout meant casual mingling, plenty of people, and—most importantly—a brand-new playing field.

    So, with a mix of optimism and mild concern, I handed over my number and braced myself for whatever came next.

    Jennifer’s Reluctant Sidekick
    Dragging a non-party animal to the social minefield.

    I know this sounds pathetic, but I practically begged Jennifer to come with me to the singles’ cookout. Thankfully, her husband understood just how socially inept I’d become without the crutch of alcohol and gave her the green light. This was no small favor—Jennifer is many wonderful things, but “life of the party” is not one of them (that crown belongs to her sister, Jackie). So, I knew she was doing this purely out of love.

    We arrived and quickly got swept into a conversation with a little huddle of other girls—clearly also there to scope out the field but far too nervous to leave their protective wallflower cluster. Safety in numbers, I suppose.

    Enter the Rat-Man.

    Matt slithered into the circle like it was his natural habitat, planting himself right next to me. Once again, he launched into conversation while I nodded, smiled, and engaged just enough to be polite, all the while scanning the crowd for any non-rodent-like knight who might swoop in and save me. No such luck. Even the wallflowers eventually found a socially acceptable escape route, leaving me trapped in one-on-one small talk purgatory.

    After what felt like several decades, Jennifer mercifully announced it was time to go. I had survived. Barely.

    Unfortunately, my survival was short-lived. Not long after, Matt called and asked me out on a date.

    Jennifer was elated.
    I was… significantly less elated.

    Friday arrived, and so did Matt. Coincidentally, my cousins and my aunt were all “visiting” when he came to pick me up. They sat at the kitchen table like a welcoming committee, smiling warmly as he introduced himself and turned on the charm.

    Eventually, he announced he’d made a dinner reservation. When pressed for details, he just smiled and said, “It’s a surprise.”

    Intriguing.

    After a loooong drive (not only in miles but in awkward silence), we pulled up to the Don CeSar Hotel—the legendary Pink Palace of Florida. I’ll admit, I was impressed. This was no casual Applebee’s date. This was full-blown romantic.

    Matt’s One-Man Show
    Hamsters, weather, and the art of not asking questions.

    We dined in a courtyard overlooking the ocean, the warm breeze adding to the dreamy ambiance. It was the kind of setting you’d see in a romantic movie—except in my movie, I was desperately wishing someone else was sitting across from me. To make matters worse, Matt did not stop talking. The entire dinner was a one-man show about Matt: his job, his hobbies, his thoughts on Florida weather, his childhood pet hamster. Not once did he ask me a single question. By the time the main course arrived, I could have drawn a detailed diagram of his extended family tree, yet he still didn’t know what I did for a living. And these were the dark ages before cell phones, so there was no fake “urgent text” to rescue me—I was trapped until the bitter end.

    By dessert, Matt was already talking marriage. At some point, I must have mentally checked out of his constant monologue—nodding and smiling on autopilot—because I suddenly realized he had probably just spent the last twenty minutes listing all the reasons why this one dinner should fast-track into a wedding date. For all I knew, he’d already picked the church, ordered the cake, and decided what our future children would be named… and I’d just been sitting there, wondering if the ocean breeze was strong enough to blow me out of my chair.

    I broke out in a cold sweat, flashing back to the Duncan Proposal Incident, and my fight-or-flight response kicked in. Since “flight” wasn’t an option when you’re trapped at a five-star resort, I chose Option C: nervous laughter and strategic subject changes.

    When I finally got home, Jennifer was practically glowing. In her mind, I was now officially on the fast track to getting a ring on my finger—just when she’d been about to lose all hope.

    I, on the other hand, had vowed never to take another call from Matt and never set foot in that church again. Now all that was left was to break the news to my poor, sweet Jennifer—who had probably already picked out her bridesmaid dress and was mentally rehearsing her toast for the wedding reception.

    Little did I know, this was only the opening act in what would become 101 Disastrous Dates in America—and if Matt the Rat was my warm-up, heaven help me for what was coming next.