real life

The 7 most cringeworthy things to have ever happened on a first date.


First dates are awkward – scratch that – they’re agonizingly awkward.

But we battle through the good the bad and the ugly, time and time again, in search of that one GREAT first date. The kind of date that doesn’t make your skin crawl, the kind of date that – bear with me – makes you smile and feel all gooey on the inside.

So while we all bide our time, the only thing we can think of that is BETTER than a great first date is witnessing someone else on an atrociously bad one.

So without further ado, here are seven of the very worst first dates we’ve ever heard – courtesy of Reddit. You can thank us later.

1. The we-have-nothing-in-common first date.

“We talked about avocados for an hour because it was the only thing we had in common.

“Anyway, like I was sayin’, Avocado is the fruit of the sea. You can barbecue it, boil it, broil it, bake it, saute it. Avocado-kabobs, Avocado creole, Avocado gumbo. Pan fried, deep fried, stir-fried. There’s pineapple Avocado, lemon Avocado, coconut Avocado, pepper Avocado, Avocado soup, Avocado stew, Avocado salad, Avocado and potatoes, Avocado burger, Avocado sandwich. That- that’s about it.”

awkward first dates
The awkwardness that was the film ‘Knocked Up’. Image via Tumblr.

2. The ‘It’s complicated’ first date.

“I found out during that she was actually married. Not even legally separated, or something. No, I did not go on another date with her.”

But wait, there are worse disclosures – much worse. Like THIS: “Met her via some dating website years ago. Two hours into the date she says she had something to “confess”.. She just got out of serving 2 years in prison for giving blow jobs to teenage boys in the group home she worked at and that she’s now a registered sex offender. Oh, and she’s married and has a a husband and 6 year old daugther at home…… Good times…”

3. The ‘You dodged a bullet’ first date (literally).

“She asked me if I would try to fight someone off or catch a bullet for her on the first date. Without think I said “hell no you must be out your damn mind”. Tried to apologize but she didn’t seem to accept it. Who asks that on a first date anyway. She got offended and we both ate our burritos in silence.”


4. The date that you don’t realise is a date.

“Met a girl on a plane who was moving to my city. We chatted the whole way back, tried to exchange contact info but failed, but later found each other on Craigslist missed connections. Very cute. We meet up for a drink, conversation is flowing, we’re hitting it off again.

We get a second round and I mention something about how I’ve recently signed up for a dating site but I prefer meeting people in real life.

She says: “Wait, is this a date?”

“Well, kinda of. Yes.”

She gets furious, throws some money at me and storms out of the bar cursing me.”

5. The deal-breaker first date.

“Met a girl online one time, seemed to be going really well. We exchanged numbers and started texting. We decided to finally meet after a week or so of texting, so we decided on a local restaurant on a Friday night for dinner.

I was waiting in the lobby and she walked up smiling. As we shook hands I started to say “nice to meet you” but was cut off halfway through saying it as she let out an earth shattering fart. I’m pretty sure it was a 7 on the Richter Scale. And the smell was just rancid, I can’t even describe it. I dropped my smile and kind of looked around at some of the employees and they looked at me like “run dude, just run”. I ended up just saying “I gotta go” and walked away.”

awkward first dates
Has there ever been a more awkward first-date-series than ‘When Harry Met Sally’? Image via Tumblr.

6. The stomach-churner first date.

“Had a first date at a local coffee shop. About halfway through the date he stands up right in front of me, plugs one nostril, and then shoots snot out the other nostril. He had a nasty white booger hanging out of his nose for the rest of the date. Right after that he texted me -while I’m still sitting at the table with him- “I really want to make out with you right now. Is that bad lol?” I told him vocally that I wasn’t down for PDA to which he replied -in a text- “I wasn’t talking about PDA lol.”

I definitely was snot down with that dude.”

7. The never-ending first date.

We met up at a local burger joint and he didn’t say a single word. I asked questions and he responded with head nods and occasionally a chuckle that’s more like a release of air.

I was pretty sure he hated me so, I told him I was just going to go home.

awkward first dates
Drew Barrymore and Adam Sandler in ’50 First Dates’. Image via Tumblr.

That’s when he finally spoke. He asked me why and told me to please stay…so I did, and then he continued to sit in silence.

Looking back now I realize he was just nervous but, man…at the time I really thought that I must have been horrible to be around.

Update: We’ve been together for 2 years and he actually talks to me now.

Now it’s over to you. What’s the most awkward date you’ve ever had? Spill.

Looking for more cringeworthy content? Try these:

These women are live tweeting period and it’s bloody funny.

A woman hilariously live-tweeted the worst Tinder date ever.