“Bloopers of the Heart” | How Not to be Awkward on a Date


Ladies, ladies, ladies. Hello, and welcome to what is essentially an exercise in humiliating myself for the benefit of others. I’m a giver, you know? And my gift to you is a list of the most ridiculous (and totally true) things I have blurted out on dates. 

So, while you are aimlessly scrolling through your phone while mentally preparing for your next date, take a few minutes to take in my shame—bask in it, as it could save you from putting your Louboutin in your mouth the way I have on several occasions. Okay, more than several. I can never shut it up. 

Let me teach you “how to not be awkward on a date.” Here we go!

serial killer

1. ‘Are You a Serial Killer?’

Look, I know for a fact that I’m not the only one who has said this out loud, but most do it in a jokey, non-serious manner. Not me, I was dead serious because I was pretty sure my date was a serial killer and wanted to make a skin suit out of me a la Buffalo Bill in Silence of the Lambs

Why? Easy. While eye contact is good, this man would NOT break it. The intense way he stared into my eyes was not only unnerving, but it scared the sh*t out of me. So I asked him if he was a serial killer, expecting him to laugh or at least stop staring into my soul. He did not laugh or break eye contact, and I swear to God his lips twitched. I said I had to go to the ladies’ room and got the heck out of there. Is this funny now? Yes, hilarious. But that night, I thought the bar was going to queue up ‘Goodbye Horses,’ and it was curtains for me. 


2. ‘I Have to Go, I’m Worried About My Dog’

The first example was a little heavy, so let’s move on to a few lighter ones! Now, you should know that my dog had his teeth cleaned, which requires sedation, so he was still a little loopy when I left for the date. 

But the man was fine, so I figured I could stuff down my anxiety over Mr. Moo (the dog in question) taking a tumble down the steps in an opiate haze. Nope! The “what ifs” kept coming while I was trying to listen to what the hot man in front of me was saying or asking when I abruptly stated, “I have to go, I’m worried about my dog,” dropped a $20 on the table and bolted. Blew that one pretty badly, and when I got home, Mr. Moo was snoozing and probably didn’t even notice my absence. 


3. ‘The Puppy!’

You’ll need context for this one. This date was with a dude I met at a dog shelter—I’d helped him fill out his application for an adoption. There was a good vibe; he asked me out, and I went. Easy enough! 

Since we met at an animal rescue, the starting small talk revolved around animals, and then this man hit me with a surreal question. He asked, “What if you were in a river and on one side, a baby is floating toward you and on the other, a puppy. You can only save one: Which one are you grabbing?” 

I immediately yelled, “The puppy!” Yes, I know I was supposed to say “the baby.” The horror on his face told me this date was done and dusted, but to be fair, what a bizarre question to ask, and he never followed up on adopting a dog. Guess it wouldn’t have worked out. 


4. ‘You Remind Me of My Dad!’

This was a compliment, but I can see how it could be insulting or even offensive to a man. You see, my dad is the man I measure all men against, but my date was not trying to hear any of that and quickly made his excuses to exit the date. And while I don’t blame him, Ben, if you’re out there, IT WAS A COMPLIMENT, MY DAD IS AMAZING. 


5. ‘Your Sister is Soooo Pretty’

Welp, this was a bad one because how did I know my date had a sister when I supposedly didn’t know anything about him? Good question, but you already know the answer; I’d stalked his IG before the date. 

That’s not an abnormal thing to do; in fact, I think it’s pretty proactive and a safety measure. The key here is to not let them know you’ve done that investigating, but my mouth got ahead of me after two margaritas, and his sister was absolutely stunning. 


6. ‘If You Were a Fruit, You’d Be a Fineapple’

I stand by this one, as we were doing the cheesy pickup line banter thing. It’s adorable, right? But he came back with, “If you were a vegetable, you’d be a cutecumber.” 

It gave me the instant ick, and hey, wait a minute, this one was his bad, not mine. Whatever, it goes on the list. 


7. ‘I Can Make a Perfect Pig Noise’

This date was doomed from the start, as I’d been out with friends before, and drinks were consumed. By the time we met up, I was tipsy, bordering on drunk (not a good look, I know), and we were talking about weird things we could do, like tie a cherry stem into a knot with your tongue, put your fist in your mouth, etc. 

My stupid human trick is making super realistic pig grunts (not the squealing noises) with the back of my throat—so I declared that and then demonstrated. To his credit, he was impressed and said it sounded just like a pig! Thanks, Jack. 


8. ‘My Mom Would Despise You’

This was one of those dates where you know it’s going to be bad, and I was trying my best to be engaging when he said that thing that boys say: “Moms LOVE me.” 

So I took him down a notch by telling him that my mom would do no such thing. Yes, it was mean. But in my defense, he was cocky and very rude to the servers. 


9. ‘You Are A Vault of Useless Info!’

This was meant as a compliment, as I am also a vault of useless info. My brain retains things that aren’t important and will not further me in life, like movie quotes, pop culture stuff, you get it.

My date was the same, and this was me saying, “You are one of my people,” but he didn’t see it that way. Bon voyage, Danny. I really did appreciate you reciting parts of Fletch for me!

alarm clock

10. ‘I Have an Early Meeting, So If This Doesn’t Work Out, I Need to Know Soon’

Tom laughed. He thought I was joking. I was not joking, Tom.


There you have it. A walk down the Hall of Shame in my dating faux pas. Now, why would I expose myself like this, you ask? Easy: I believe in the healing power of laughter, even if it’s at my own expense.

The thing is, dating disaster moments make the best stories, don’t they? Plus, if we’re not messing up, we’re not really trying, or so I like to tell myself.

So next time you’re preparing and are googling “how to not be awkward on a date”, take comfort in the fact that the bar is set pretty low. No matter how bad it gets, at least you can say you’ve never asked a man if he’s a serial killer within the first five minutes—and meant it. 

Even if you stumble and fall flat on your face, pick yourself up, laugh it off, and get back on that dating horse. I’ll be right there beside you, probably saying something absurd.

Ready to get back on the dating horse? Check out some of our recommended dating apps!

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