The Tale Of A Date Gone Wrong

Dating experience | | , Journalist, Content Strategist & Editor
Updated On: May 24, 2021
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The setup doesn’t match the expectations one would have about a first date. The place is dingy, dimly lit and the music too loud to my liking. If you ask me, that is the recipe for a date gone wrong. But such would be the place you end up in Delhi when you have sex on your mind and a massive hole in your pocket ahead of a first date encounter.

The Story Of A Bad First Date

I’m gulping down pints of the cheapest beer available, one after another. She looks uncomfortable already, still on her first mojito, and keen on making conversation. Her conversation starters were not too bad but I kept changing the topic. I drift away from topics better than our current prime minister. Or not respond to certain topics at all, again, like our prime minister. I already had a feeling this was going to be an awkward first date.

Conversations have ceased to interest me after the terrible breakup I had. What I still have though – and what still has all my interest – is an unsatiated sex drive. Since dating apps have made meeting strangers so easy, you don’t think about finding true love.

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What you look forward to often, is a one-night stand. Millennials call it “finding friends with benefits”. No, I am not on Tinder to find true love, and honestly, that is the lamest excuse I’ve heard in a century.

At the risk of stereotyping women in Delhi, she’s not one of them. No tattoo, no blonde highlights, no Da Milano purse, no high heels and no “LBD”. Wearing a pair of blue denim jeans and a white sleeveless crop top, she’s sitting across the table, looking at me. At this point, when I am done with my sixth pint, when she’s only halfway through her mojito, she pulls out a band from her left hand and ties her hair into a bun.

Related Reading: Does A Friends With Benefits Relationship Actually Work?

I drank too much

“Dude! I didn’t know you’re such a fast drinker,” she says.

“Ah. Not always. I am fast at everything, by the way!” I say without an ounce of embarrassment. My idea of flirting. My friends have often told me that my moves can qualify as the top flirting mistakes guys make. But I’m a confident guy looking to get laid, I take it in my stride.

“I will be done with this in another ten. Can we step out and go for a walk, if that’s fine with you?” she asks.

“A walk. Ugh! That’s too demanding, I’d say,” I say, patting myself in my mind for being rude without a reason. “I’ve a car. We can go for a drive instead. You know, long drives, some good music, and some good fun.”

“No. Not tonight. You’re already high I see,” she says.

“Me? High? Hah! Never. I can fly a plane. Let me take a leak and we shall step out. Finish your drink at least,” I say, struggling to pull myself to my feet, falling back on the couch multiple times while I am at it.

awkward first date
I was too drunk and she was not willing to put up with it

“I have no doubt you can fly a plane. Stand straight, first. We shall fly planes later. We are not going for a drive.” She’s no-nonsense, I realize soon enough.

“Shall we at least go sit in the car, ma’am? Spare me this music,” I say, finally managing to get up. “We can go to my place too. Or yours, if your flatmates wouldn’t be around,” I say while steering myself to the washroom. I don’t wait for her reaction.

Related Reading: 20 Valuable Tips For A First Date After Meeting Online

Ready to leave the pub

I see she’s paid the bill by the time I got back, and is ready with her backpack by her side. Her glass still had some mojito left.

Chalo!” I go close to her, trying to hold her by her waist but her backpack proves a hindrance. She notices, and naturally, gets more uncomfortable. She brushes away my hand gently, with an awkward smile, and starts walking toward the door. One of the obvious signs of date night gone wrong.

I get my cue that this has become an awkward first date, but when you’re six pints down on an empty stomach, when there’s only one thing on your mind, and when that one thing is sex, you don’t give a crap about how you’re making someone else feel.

Even if that is on your first ‘official’ date. Even if you’re meeting this person, a woman, for the first time. Too much alcohol in your system, an ugly breakup, and a corporate noose around your neck can make you nothing short of a dick.

Well, most men are dicks. By default, from birth. Thank patriarchy for that.

I try to keep up with her pace of walking, but boy, is she fast! I’m sure she notices I am not with her, but she doesn’t stop, doesn’t turn around to see if I’m still with her. I figure she’s walking toward one of the Metro entrances. I manage some energy, walk faster, and grab her by her hand.

She stops, turns around and gives me a death stare. “Wow. I’m sorry, what’s the matter?” I ask as if I am completely unaware about this date gone wrong.

Just let me go

“What’s the matter?”, I asked.

“Nothing, really. I guess you should go home and get some sleep. I need to go too,” comes the answer.

“Oh, come on. I genuinely don’t know why you’re mad at me. Is it because I drank this much? I’m fine, can’t you see? I told you I can fly planes even when I’m sloshed,” I say. Lately, I’ve been amused at how shameless I’ve become.

“Dude!” she stopped walking and turned around.

“You know what? Good luck with flying planes. I really need to go,” she says, looking straight into my eyes. Tough woman, I see. I’m attracted to that.

“But…I thought there’s more to this date. You know…fun stuff!?” I stoop lower than I ever have.

“Oh! Is that it? You thought you’d get to screw me tonight? Was that the plan all along? Get your date drunk, take her for one of your “fun-long drives” and get some casual sex? Is that what you usually do?” her voice, I’m sure, is heard across the street, despite the traffic and all the honking.

“I see you’ve completely misunderstood me. I know things didn’t go very well back there, but it’s not how you think. Please let me make it up to you,” I say.

bad first date
She clearly was not amused and it had turned into a bad first date

Of course, it’s exactly how she thinks. That’s what is on my mind. It is true, I wanted her to get drunk, come for the drive, and let me screw her. But of course, those are not the kind of things you’d tell someone, right? Especially a woman. Particularly on a first date.

“Not tonight. Tonight is over.” She is firm.

Related Reading: Mistakes men should avoid when on a date

How about that walk then?

“Come on. I am sorry. I really am. Let’s set this straight. No. Let me set this straight. Let me take you someplace nice. And we will talk. Or we can go for the walk you suggested earlier?” I say, thinking to myself that I’m good at this and I can save this date gone wrong. I knew how to make up after a fight.

How will I not be good at this crap? All throughout the five-and-a-half-year-relationship, I’ve profusely apologized, even for things I needn’t have apologized for. If a man asks me for advice before taking the plunge and telling a woman that he’d like to be with her, I’d tell him “say sorry”. If you apologize, you win. It is also the perfect way to save date night gone wrong.

But not here. Not with her.

Sorry is not enough

“I told you once, and I guess I made myself pretty clear. Not tonight. You had one job tonight, and that was not to fuck this meeting up. Before deciding to meet, we have spoken to each other for quite a while and I’ve told you more times than I can remember that I’ve been a master at dating the wrong men. I told you how the slightest tendency in men to ‘speed up things’ turns me off, and I’ve told you a thousand, million times how I take a lot of time to trust someone, regardless of their gender, but especially men. And you? Despite knowing all this, you mess this up.”

dating disaster

“So no, you don’t get another chance tonight. I don’t even know if you’d get another chance later. You should go home, and if you get home and get some time to think about what happened back there, I want you to remember these words. Good night. And do not follow me and make this scene a lot worse than it already has become,” she says, leaving me no other option other than to try and act as if those words matter to me, behave as if I’m hurt and try to make her believe that I repent my deeds and words. This first date gone wrong was not new to me. I was not hurt at all really.

Related Reading: How to run away from a bad date

I’m not defeated though

“Alright. Whatever you say. I messed up, and I messed up big. My bad. I shouldn’t have, but I did. So you go ahead, get home. I won’t follow or text you till I figure out what happened and why. But you will hear from me soon. I will not let one bad meeting define what we have,” I say.

Bloody hell, I should quit my banking job and be a chick-lit writer instead. She walks away. And I’m stranded on the streets of Delhi, Connaught Place to be precise, wondering to myself if I should just get home or try to get in touch with the other chick who had texted me a couple of days ago saying she’d like to meet.

Say what you will about double texting, but thanks to it, I have backups. A lot of them. Just that nothing ever goes the way I expect it to unless I put in a lot of effort. That’s the one thing I can’t do anymore. Making efforts. I am tired of it. I’m tired of being nice. I’m tired of being the ‘gentleman’, I am tired of being who everyone wants me to be. I don’t care about a date night gone wrong because trying to make it work seems exhausting.

I am tired of being me.


1. What to do if you messed up the first date?

You have to be honest and come clean about what made the date so awkward. Be yourself, try to be accommodating and suggest a change of activity. Do something to make the other person feel comfortable or at ease even if that is just playing a board game or ordering another drink. Stop flirting and just try to create a comfort zone.

2. Is it normal for the first date to be awkward?

It can be. Sometimes when people are shy or not used to going on dates often, they might get awkward quickly. Moreover, when a couple doesn’t hit it off, you might start seeing signs of a first date gone wrong.

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