Bad Experiences from Swipe-Rights and Gig-Sites
Ah, Valentine’s Day — the annual reminder that love is in the air… or, at the very least, that heart-shaped chocolates are half-price tomorrow. Whether you’re blissfully coupled up or single and thriving, today is the perfect time to reminisce about the universal experience that unites us all: bad dates. Those cringe-worthy, facepalm-inducing, “why did I leave my house for this?” encounters that make you seriously consider adopting a dozen cats and calling it a life.
Modern romance – like the gig economy – is a wild, unpredictable adventure full of high hopes, minor heartbreaks, and the occasional desire to throw your phone into the ocean. Dating apps and gig marketplaces promise endless possibilities, yet somehow, both can leave you questioning your life choices and eating ice cream straight out of the container.
Much like swiping right on what seemed like your dream match, hiring a freelancer (or taking on a new client) can feel promising at first. You start off hopeful, thinking, This is the one! — only to find yourself in a downward spiral of ignored messages, unrealistic expectations, and an existential crisis over why you ever thought this was a good idea.
We’ve all had bad dates. We can all probably relate to the following stories and have our own version of one of these horrible dates and our version of “the one who” — the one who ghosted, the one who overshared, the one who showed up late, or the one who brought their mother to dinner.
Much like dating disasters, bad business relationships can leave you with regrets, confusion, and the overwhelming urge to change your phone number. So, let’s take a moment to relive the horror — and laugh through the pain — as we dive into some truly terrible encounters that prove one thing: whether it’s dating or freelancing, finding the right match isn’t always easy.
The One Who Was a Catfish
You match with someone who seems perfect — charming, well-dressed, and with a profile pic that screams “I have my life together.” But when they show up, it’s clear their photo was taken at least ten years ago, in significantly better lighting, possibly on another planet where good hair days never end. Their “six-pack abs” have mysteriously transformed into a well-loved hoodie, and suddenly, you’re regretting not making an emergency exit plan with your best friend and not having an excuse to leave.
Gig-Site Bad Freelancer: The portfolio was dazzling, the reviews glowing, and the initial pitch sounded like they were the perfect fit. But once work begins, it’s clear that their “expertise” is more wishful thinking than reality. Subpar work, missed deadlines, and the sinking realization that you’ve hired someone who’s much, much different than you thought they were.
Gig-Site Horrible Client: They described themselves as an “innovative, forward-thinking company” with a “clear vision” and a “healthy budget.” Reality: no plan, zero clue what they want, and somehow expect you to read minds while working “for exposure.”
The One Who Had No Faults
You casually bring up how showing up an hour late wearing pajama pants wasn’t the best first impression, and they immediately turn the blame on you. “Wow. Well, you didn’t exactly help pick the place we’d meet; it was your indecision that left me scrambling to get ready and make it on time.” Clearly, their lack of planning, bad manners, and inability to choose a restaurant are somehow your fault.
Gig-Site Bad Freelancer: You ask for a minor revision, and instead of addressing the issue, they go on the defensive. Suddenly, you “don’t understand my creative process,” completely ignoring the fact that their design looks like it was made from clip art from the era of America on Line.
Gig-Site Horrible Client: They change the scope, miscommunicate expectations, and send you conflicting feedback — but somehow, “You should have known what I meant,” all while emailing you yet another contradictory request.
The One Who Disappeared
Things were going great. You laughed, shared a dessert, and even talked about a second date. Then, the next day — nothing. No texts. No calls. Just radio silence, as if they were abducted by aliens or entered the Witness Protection Program overnight. Even after the 3-Day-Rule has expired, they’re still a ghost.
Gig-Site Bad Freelancer: The first few messages were prompt and enthusiastic. The project kicked off with excitement. Then… nothing. Emails go unanswered, updates are non-existent, and your project deadline is rapidly approaching with no sign of life from the freelancer.
Gig-Site Horrible Client: They promise feedback by Friday, then vanish into the abyss. Weeks later, they resurface with last-minute demands, expecting you to turn things around overnight.
The One Who Had Lots of Other Options
You’re halfway through dinner, sharing a heartfelt story, when you notice them blatantly checking their phone… and seems to be swiping on a dating app. They’re already shopping for their next match before you’ve even finished your entrée.
Gig-Site Bad Freelancer: You hire them, only to realize you’re just one of a dozen projects they’ve taken on at once. Every deadline is delayed, responses are rushed, and it’s clear they’re prioritizing other clients’ projects over yours.
Gig-Site Horrible Client: They treat you like a backup option, constantly reminding you that they have “other freelancers lined up” if you don’t meet their impossible demands.
The One With a Thousand Excuses
They’re late because of traffic. They didn’t text back because of a phone malfunction. They forgot their wallet at home because they dribbled toothpaste on their pantleg and had to change last-minute before running out of the door to make it to dinner on time. They have to leave early because their dog needs to go to the vet. If excuse-making were an Olympic sport, they’d have more gold medals than Michael Phelps.
Gig-Site Bad Freelancer: Every missed deadline comes with a new excuse — the file got corrupted, the internet went down, I had a family emergency, Mercury is in retrograde. The list never ends, but your patience does.
Gig-Site Horrible Client: I like it, but it needs one more revision; the approval needs one more VP to sign off, but will be by end of week; the final revision needs just one more change and then the CEO will take a look at it and will probably approve … probably that will be the last modification. You didn’t get the check? I asked Accounting to send that out the other day. I’m sure the check is in the mail. Spoiler: it never is.
The One Who Wouldn’t Let Go
The date seemed fine, not terrible, not great — just fine. But to them? It was magic. They’re already planning your future together, blowing up your phone with “what you up to?” texts, and tagging you in memes about soulmates. By the third unsolicited paragraph-long message, you’re contemplating faking your own disappearance.
Gig-Site Bad Freelancer: You wrapped up the project, paid them, and thought it was done. But then come the follow-up emails, with updated drafts, modified copy and content, and invoices for changes and consulting you never agreed to.
Gig-Site Horrible Client: You completed the project, delivered beyond expectations, and moved on—except they didn’t. They keep coming back with “one more tiny tweak,” “just a quick fix,” or “since you already built this, can you add 10 extra features … for free?”
The One Who Forgot Their Wallet
You go out for an elegant dinner. They order the steak, an extra appetizer, and a premium cocktail with each course of the meal. When the check arrives, they suddenly pat their pockets, look concerned, and dramatically exclaim, “Oh no, I must have left my wallet at home.” You end up paying, wondering if you’ve just been scammed into providing a free meal.
Gig-Site Bad Freelancer: They agree to the work but suddenly start asking for extra tools, software, or subscriptions—on your dime. Or worse, they vanish right before the final milestone, but invoice you anyway.
Gig-Site Horrible Client: They promise great exposure instead of payment, swear they’ll pay after the next funding round, or insist that this experience will look amazing in your portfolio. Somehow, the invoice is always delayed, lost, or just never processed.
The One Who Talks Endlessly But Never Says Anything
They talk a lot — about their job, their ex, their childhood pet hamster — but somehow, none of it is interesting. You’re nodding along, zoning out, and trying to remember if you left the oven on, while they go on a 20-minute monologue about their favorite sandwich.
Gig-Site Bad Freelancer: They promise updates but never deliver anything substantial. Every email is long-winded and full of buzzwords, yet somehow, the actual work is nowhere to be found.
Gig-Site Horrible Client: They hold meeting after meeting, write paragraphs of unclear direction, and use vague phrases like “Make it pop” or “Just do your magic.” You’ve read their email five times and still don’t know what they want.
The One With The Advice
You mention that you like to run on weekends. Suddenly, they’re lecturing you on optimal shoe choices, hydration strategies, and why you should really be doing barefoot trail running at sunrise. You didn’t ask for this, but here you are, being coached and second guessing if you should have ever started running in the first place … or maybe should start running, right now, for the exit.
Gig-Site Bad Freelancer: You hired them to do a logo. Now, they’re giving you business strategy advice, telling you how to market your company, and explaining why you should change your brand name entirely.
Gig-Site Horrible Client: You’re a designer, but they keep telling you how to edit photos and align text. You’re a writer, but they’re explaining grammar and the oxford comma to you. Somehow, they know just enough to be dangerous but not enough to be helpful.
The One Who Brought a Friend
You arrive at the restaurant at the agreed upon time, you find them seated at a table … but they’re not alone. Surprise! They brought their best friend. As if the third-wheel isn’t bad enough, the friend dominates the conversation and openly shares their opinions about your compatibility – a lot of opinions. It is less a date and more a bizarre social experiment. You find yourself constantly looking around, scanning the room for hidden cameras and Ashton Kutcher or Allen Funt.
Gig-Site Bad Freelancer: You hire a freelancer based on their stellar reputation, only to find out they’ve delegated your project to a junior colleague. Communication is a mess, quality drops, and no one seems to be on the same page.
Gig-Site Horrible Client: The person who hired you seems reasonable — until their coworker starts chiming in on every decision. One says, “Make it bold!” while the other says, “Make it subtle.” Revision requests skyrocket, and suddenly, your job is more about playing referee than delivering work.
Finding the Right Match
Like dating, finding the right freelancer or client takes effort, patience, and a good eye for red flags. Not every match is a good one, but when you find the right fit, everything just works. Communication is effortless, expectations are clear, and projects feel exciting instead of exhausting.
And let’s be honest—just like dating apps aren’t the best way to find true love, gig platforms aren’t always the best way to find top-tier talent. That’s where a more curated, personalized approach comes in.
When you work with FlexTal, that’s also where a Customer Success Manager (CSM) changes the game. Instead of wading through a sea of mismatches and crossed signals, you have someone in your corner ensuring the right connections happen from the start. A great CSM doesn’t just introduce you to the right freelancer or client — they also help keep things running smoothly. They act as a liaison, helping to set expectations, mediate any hiccups, and make sure everyone stays on the same page so projects don’t spiral into chaos.
So, if you’re tired of getting ghosted, catfished, or stuck with a bad match, maybe it’s time to let the professionals handle it. Skip the heartbreak, dodge the disasters, and find your perfect business match with FlexTal. Reach out today, and let’s make sure your next working relationship is one worth committing to.
Chris is the President & COO of FlexTal. He brings 20+ years of experience in Customer Success, UI/UX, design, and marketing – including time within start-ups, agencies, and enterprise orgs. Chris has also served as a University adjunct professor in Advertising & Public Relations for several years.
