My 6 Worst Dates Ever On The Road That I’d Like To Forget

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Sometimes guys I’m dating, seeing or what not, ask me if I’m going to write about them in the blog. Well congratulations guys…today is your lucky day. I’m 34 next week and in the last 8 years of travelling I think I might just have the best record for the worst dates ever. Feel free to prove me wrong and share your woes in the comments below.

I’m not angry or full of bad vibes on this. Instead, I’m openly laughing about it and putting it out there. How I’ve got to this point is a mixture of bad decisions, not having the time to get to know people properly (travel cons) and wearing rose-tinted glasses. And hanging out with the not-so-best choices sure does lead to a fun 10 minutes of storytelling!

Worst Dates Ever On The Road I'd Like To Forget

My 6 Worst Dates Ever On The Road I’d Like To Forget

So without further ado, to get rid of my bad voodoo forever and embrace this new life chapter (I’m finally getting a base in the UK for a bit of routine and steady dating) here are the top 6 worst dates ever I’ve had the (dis)pleasure of experiencing on the road. Enjoy.

The Meatball Stoner

A confusing case for sure, as he was 50% terrible and 50% incredibly caring. He always made sure that I was well fed. He asked regularly if I needed anything. He’d genuinely say sweet things and even drove cross-country, into another one, to see me.

Yet, he turned up high as a kite. To the point where he couldn’t see straight. We went out for a romantic dinner. Meatballs.

Before the bread has even come out he tells me about how he went on a mission to sleep with a hooker in Amsterdam…and oh boy did he do it. He tells me about all the women he’s been sleeping with for the past couple of months too, but I’m still the best he’s had, ‘…so it’s all good’. Thanks buddy. Check please.

Lesson learnt: If you’re dating other people, best keep the deets to a minimum eh? Hooker stories included. 

The Dip Dabber

Ladies – bet you’ve come across this one. The one who wants in, even though you’re saying no. The one who just won’t take no for an answer and keeps trying, even though you’ve made yourself clear. I ask my friend before I make a move if he has a good reputation in town. ‘As far as I know, he’s a good guy’ she says.

Turns out she hardly ever goes out in town to know his reputation well enough, and he’s hooking up with every girl within a 5-mile radius. Found that out the hard way when girls started coming up to me asking what I was doing with ‘their man’. Yeesh.

Lesson learnt: Make sure your date understands what glove shopping is and the word ‘no’. Ask more than one friend for a character reference.

The Silent Alcoholic

This is a guy who I decide to go and meet after we get off to an amazing start in Thailand. We’re both excited to see what happens, but as soon as I turn up, he’s terrified. So terrified that he’s drinking heavily and playing computer games online so he doesn’t have to talk to me…in the tiniest apartment we’ve both probably shared with someone.

After 3 days, it gets to the point where I feel so isolated and can’t get him to communicate, that I plan to pack my bags and leave the next day whilst he’s at work. As I’m about to walk out the door with my backpack, he calls to ask if I want to meet him for lunch. I say yes.

I leave my stuff in the apartment and walk out the door (with the keys to the apartment accidentally falling out of my jacket). As soon as lunch is over, I run back to the apartment and realise I don’t have the key to get back in. I have no phone either, so have to wait on the steps for 4 hours until he gets home and explain everything. We manage another 2 days together, but it’s absolutely agony. When we finally depart, he shouts, ‘Until we meet again for Date 3’. Urgh. No way dude. No way.

Lesson learnt: Communicate. If that’s not possible – get the hell out and remember the keys.

Worst Dates Ever

The Tinder Box

Why oh why do I even go on Tinder? I know some of you have found true love through it, but I’ve had nothing but epic fails. There’s been some right old stinkers, but meeting this guy takes the biscuit. After a really cool date and making out, he then talks for an hour about how he’s heartbroken and that his ex is the most beautiful girl he has ever met. And he hasn’t met anyone like her ever since.

I’m your date. Not your therapist *face palm*

He tells me his exact track history of dating on Tinder too, and all the tricks he uses to see if girls are up for it or not. How the hell did I end up with this one?

Lesson learnt: Never use Tinder ever, ever, ever again.

The Oxford Car Dilemma

For a period of time I’m back in England and trying to do the ‘right thing’ by dating a fellow Englishman. He likes country walks, green farmer jackets, drinking wine in pubs and chess. He went to Oxford.

He finds it weird that my accent changes from American to English to half-Asian. He also finds it amazing how I sit cross-legged on his bench at the dining table. Travel does that to you.

Regardless of our cultural mix-ups, he is the loveliest of the lot here – but when it comes to money, the relationship is officially over. I’m dating him whilst still owning my car from the Mongol Rally – which all of my neighbours hate for ‘bringing an eyesore to the street’. Honestly, who doesn’t love fluorescent pink cars covered in graffiti on their street?

Unfortunately, ‘Babs’ the Toyota Yaris doesn’t make it past her MOT. She needs hip replacements that cost thrice the price of her, so I have to start thinking about getting a new ride. ‘What are you going to get?’ he asks. ‘The cheapest’ I say. ‘You can’t be serious’ he replies. ‘As long as it moves and has 4 wheels, I couldn’t care less’ I respond. The look on his face is priceless. We break up a week later.

You need to have a good car to date him (which were his priorities and that’s all cool). But I just wanted to travel to India.

Lesson Learnt: Sometimes you’re just going to value different things at different points in your life

The Mongol Rally Tracksuit Man

We met at the start line of The Mongol Rally and spent most of that 3 month journey together. He really liked wearing tracksuits. I thought he was cute. He wasn’t.

Things got weird when he got his knickers in a twist about how I brush my teeth before eating breakfast. Then he told me that I looked s**t when our teams met up in the Stans (I had been driving through the desert for a month – I’m not exactly applying Estee Lauder right now matey).

But things really got to next-level-bad when I ended up sick in hospital in Russia for 2 weeks whilst he flew back to the States. He told me he was too busy to talk to me then broke it off on my birthday. You just gotta laugh really.

Lesson Learnt: Don’t date guys in tracksuits?

What have your dating experiences been like on the road?

Happy stories welcome.

Tragedies warmly heard and empathised with.

Comment below!

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16 thoughts on “My 6 Worst Dates Ever On The Road That I’d Like To Forget”

  1. When I was 18, I was chatting to a guy whose profile picture was fairly far away and told me he was 6”3. Now I’m fairly tall (5”9) and we agreed to a date in which I wore a pair of high heels. A few moments later, this guy comes up to me who is NO BIGGER THAN 4FT TALL and has half of his skull removed. Still, I felt bad and went on the date anyway where he proceeded to talk about his ex girlfriend THE ENTIRE DATE.
    Moral of the story? Don’t trust anyone who lies about their height

  2. My advice with the tracksuit man is to just not date wankers (but they do sometimes slip through the net). Long time since I’ve been on a date mind…it would bloody well terrify me

  3. Is it okay to laugh? I feel your pain because some of it is so relatable! I have met absolute creeps on Tinder. Atleast you didn’t end up marrying one of these guys like I did and realised a bit too late haha.

  4. I feel your pain girl!! Sometimes you can meet the best people on the road, and other times they just don’t fit! Keep at it though, you will find the right one eventually. I meet my current boyfriend while working on a cruise, so also quite an advenuture.

  5. Ooof those stories bring back all the bad dates I’ve experienced as well. Here’s one for the books. Whilst living in Germany. I went on a date with a fellow who was quite normal. At the time I was living with my male friend who I was trying to avoid as he cock-blocks every one of my chances of having an actual date. So, my date and I are walking around town with ice cream cones in our hands and chatting and nonchalantly I explained to Mr. Seemingly Normal that I’d rather walk in the opposite direction for fear of running into my roommate as I think he’ll kick me out<—joke. He didn't get it. Next day he sends me a message saying that he spoke to his friends about my bad joke and they all insisted I wanted to move in with him and he told me thats not his game.
    Moral of the story: no one is ever seemingly normal.
    2nd moral of the story: don't joke with non-joke prone people.

  6. Never before have I been so happy that I date women rather than men. How do ya’ll do it?! (Disclaimer: I’ve had some really bad dates, but I would classify a majority of my no-go’s just “so so” rather than “oh god get me out of here”).

  7. Bahaha these were funny. But unfortunate. Awful dates are truly the worst sometimes.
    I once caught the travel lust after meeting a dreamy Australian while in Wales. I flew all the way to Australia, where he informed me upon arrival that he was back with his girlfriend. Would’ve been a nice thing to know before flying 30 hours to the other side of the world. Luckily I hadn’t flown there just for him, and it ended up being the greatest solo trip I’ve had! I’ve always thought of it as a win.
    (Also, why do people find sitting cross-legged to be weird? I do it all the time.)

    • Hi Danielle! Yessss! Atta girl – love it that you made the absolute most of Australia once you got there. You turned a surprising event into an amazing experience. That’s a good approach to life :) Keep on travelling and making the most of what life throws at you.


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