Spooky Dating Scenarios: How to Handle Awkward Encounters

Oct 14, 2024

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Hannah Feminella

Picture this: it’s a beautiful October evening, you’ve just matched with a hottie, and now you're heading to a dimly lit bar for your first date. The atmosphere is perfect—crisp air, cozy vibes, and just a hint of magic in the air. But then, it happens... one of those spooky, absolutely cringe-worthy dating moments you hoped to avoid. Don’t worry—you’re not alone! In the spirit of spooky season, let's dive into some eerily awkward dating scenarios and how to handle them like a pro (or at least fake it till you make it).


The Silent Treatment: When Conversation Dies Faster than a Horror Movie Character

You’ve sat down, ordered your drinks, and suddenly… silence. You’re desperately searching your brain for something—anything—to talk about, but absolutely nothing comes to mind. The conversation has flatlined faster than the first person who says, "I'll be right back" in a slasher flick.

How to Survive: First, breathe. Awkward silences are natural. If small talk isn’t cutting it, go for a bold pivot. Ask something unexpected, like, “What’s the weirdest Halloween costume you’ve ever worn?” or “When’s the last time you pooped your pants “ or “What’s your go-to zombie apocalypse survival plan?” These types of quirky questions can break the ice and kickstart the convo.

Pro Tip: If the conversation is truly dead, it might be time to revive your ghosting skills (in the ethical way, of course). Some people just aren’t great conversationalists—no harm, no foul.


The Exorcist: When They Won’t Stop Talking About Their Ex

You’ve barely gotten through introductions, and already they’re deep into a conversation about their ex. It’s like their past relationship is haunting the date, and no amount of sage or holy water is making it go away.

How to Survive: Don’t be afraid to set some boundaries with a lighthearted touch. Try something like, “Wow, your ex sounds intense! But enough about them, let’s focus on us.” This can lighten the mood and gently steer the conversation back to the present. If they’re a repeat offender, it might be time to break out your escape plan.

Pro Tip: If they can’t stop comparing everything to their ex, well, take that as a sign babe. They’re probably not be as over it as they think. 


The Accidental Overshare

Imagine this : you’re sitting across from your date, having a perfectly normal conversation when suddenly—bam!—they hit you with an overshare. We're talking next-level personal information that no one should spill on a first (or even third) date. Maybe they start talking about their weird toe-fetish or give you a play-by-play of their parents' divorce.

What to do: First off, don’t panic. This isn’t a crime scene; it’s just an unexpected plot twist. The key here is to nod politely and pivot the conversation. You could say something like, “Wow, that's... a lot. Speaking of intense, have you seen *insert any random popular show* lately?” Smoothly steer the chat back into safer waters.

Pro tip: Sometimes people overshare when they’re nervous, so give them a pass… unless it’s really weird. 


The Social Media Flex

Ah yes, the date where your companion spends half the time showing off their Instagram “aesthetic” or humble-bragging about how many followers they’ve got. It’s like a non-stop highlight reel, and you’re just the unlucky audience.

What to do: Handle this one with a good-natured eye-roll and a clever comment. “Wow, I had no idea I was sitting with a social media celebrity! But hey, tell me something I can’t find on your profile.” It’s playful but sends a message: you’re here for real connection, not for a social media resume.

Pro Tip: If they can’t tear their eyes away from their feed, it might be time to tear yourself away from the table.


The Endless Monologue (Also Known as The Lecture)

You ask a simple question, like “Do you enjoy hiking?” and suddenly, you’ve triggered a 45-minute TED Talk on the history of trekking poles. You nod politely while secretly wondering if you’ve wandered into some parallel universe where you’re doomed to listen forever.

What to do: Time to channel your inner improviser. A light-hearted interruption can be your best friend. Try saying, “I love that you’re passionate about this, but I think we should switch gears before I enroll in a class on it!” Humor will help break up the monologue. 

Pro Tip: If they don’t get the hint and keep droning on like an audiobook on loop, it might be time to take a mental note : no more open-ended questions!


The Shape-Shifter: When Their Profile Pic is a Total Lie

You’re scanning the bar, waiting for your date, and then you see them. Or at least, you think you do. But instead of the chiseled jawline and charming smile from their profile pics, you’re greeted by someone whose selfies seem to have been marinated in filters for years. 

How to Survive: You could ghost right there and then, but let’s be real—you’re already here, and running is a bit dramatic. Instead, approach it like a Halloween trick: “Oh wow, you look… a lot different in person! Care to explain? ” Keep it light and playful, but if their profile was a complete fabrication, it might be a sign to make your  exit.

Pro Tip: Trust your gut (or spooky sixth sense) If someone’s online persona is vastly different from reality, they might not be the most authentic person, and that’s a big red flag—spooky season or not.


The Ghost: When They Disappear Mid-Date

You’re halfway through a drink, telling your best Halloween story, when suddenly… they’re gone. Maybe they claimed they had to use the bathroom or take a call, but 15 minutes later, you’re still sitting there, wondering if you’ve been ghosted in real time.

How to Survive: First, check to make sure they didn’t vanish into thin air (or more realistically, skip out on the bill). If they truly ghosted, send a quick text to confirm, and then channel your inner scream queen (quietly). You’ve earned the right to treat yourself—finish that drink, order another, and enjoy your newfound freedom. Sometimes, a ghosting is a blessing in disguise.

Pro Tip: Bring a backup plan to all dates. Have a friend ready to meet you for an after-date drink or dessert, so you can laugh off the experience. Trust me, you'll get great mileage out of your ghost story.


As you can see, awkward encounters are sometimes just part of the package. However, instead of letting those moments send you running for the hills (or the door), I say own it. Laugh at the weirdness, make light of the slightly uncomfortable, and remember that everyone’s just trying their best. If all else fails, you’ve at least got a great story to tell your friends (or put in your dating profile). 

So next time you’re stuck in an awkward moment, take a deep breath, crack a joke, and remember—you’ve got this. Dating might be a little scary, but it’s also a wild, weird, and totally worthwhile ride. Happy dating my babes, and may all your dates be more treat than trick this October. Until next time x