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

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!

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.

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?