Date Report: Crushed by Rejection on Vacation

Most people go on vacation with friends or family, but I travel to be alone.

I'm an introvert. I love idea of spending my holiday beside the pool with a good book. Then at some point - usually a week or so into the trip - I start feeling lonely, sexually frustrated, or both. That's when adventure happens.

My latest trip consisted of two weeks in Bali. In case you're not Australian I'll explain: Bali is vacation Mecca for the working class. The surf is great, the dollar goes a long way, and the plane trip from Oz is short. So Aussies abound: hanging out in central Kuta feels just like being on the Gold Coast, but with narrower streets.

Sitting out the front of my hotel, cocktail in hand, I saw a parade of young folks making their way up and down the beach. I figured that picking up on Tinder would be straightforward. It's vacation, right? surely everyone would be looking for fun and new experiences?

Unfortunately, things didn't go according to plan.



Date #1: the Manchester Lad

I'll admit that I wasn't swiping using my usual good judgement. Surfers are not my scene - I prefer serious Melbournians, the intellectual type who know the difference between pour-over and cold-drip coffee. Manchester Lad was the complete opposite: he looked like an Instagram travel model. He was alluringly Mediterranean with fashionable stubble. He was visiting from the UK with a few friends.

He brought them on the date.

We met at a swanky beachfront bar in Seminyak. Manchester Lad was ordering a beer at the swim-up bar as I arrived; I splashed across in my tiny black bikini to introduce myself. The whole place was infested with beautiful people. They swarmed at the edge of the infinity pool where the glass met the beach, taking care to keep their cocktails, expensive sunglasses, and perfect hairdos out of the water.

Once I'd met my date I discovered that the nice London boys I'd asked for directions on arrival were actually his travelling companions. They were hanging around a few meters away. This caused me to feel some performance anxiety.

C'mon dude. Why bring your friends on a date and leave them waiting for you by the side of the pool? Were we all supposed to bond like a happy family? They were affable, but easily distracted; every few minutes a bikini-clad eighteen-year-old would wander past, and they'd all start trying to chat her up.

When my date told me he'd decided to call it quits, I wasn't sure whether it was because I'd told one too many anxious dirty jokes, or whether he was holding out for someone ten to fifteen years younger.

The lesson I learned was: don't meet your Tinder match at a place where everyone else is hotter and younger than you.


When you go on a lot of dates, rejection is an inevitability.

It's a blessing in disguise - when my libido is raging my judgement can become impaired. sometimes the lack of chemistry needs to be pointed out by someone else. I try to cultivate a healthy attitude: being knocked back stings, but it's better to rip the band-aid off all at once.

I'm lucky though. Guys get rejected more than I do .. so do my friends who don't happen to he young, straight, white, and conventionally attractive. I'm usually pretty good at sucking up rejections when they do happen, knowing that I'm treated better than a lot of other folks.

On this occasion I had trouble keeping that perspective. It hit me really fucking hard, basically.

Like a mohito on a hot day, the joy was sucked out of me. I retreated to a local hotel, ran myself a bath and questioned the validity of my existence. What was wrong with me? Was I going to get laid ever again?



Date #2: the Nice Guy

My second match came through just as I was falling asleep in the bath. And this is where I really fucked up - I could have just said no, right? I had a funky hotel room with a free minibar and a wide-screen TV - why not quit while I was ahead? But some little primal instinct in my brain said 'If you get laid, you might feel better about yourself."

Let me tell you folks, NOTHING good ever comes of that particular impulse. Because even though you might be thinking 'I'll feel better if I succeed", you're not thinking "...but what happens if I fail?"

Off I went, back to the same bar like a lemming to the edge of the cliff.

You know when you meet someone, and you instinctively know they’re a good guy? I don’t mean all those folks who aggressively proclaim how nice they are to women; I just mean someone who’s chill, friendly and clearly considerate to everyone he meets. This was date #2 – a fresh-faced Melbourne advertising creative. He too was here with friends, but at least he had the good manners to leave them right over the other side of the bar. And he offered to buy me a drink – bonus for being considerate!

Mr Nice Guy was quintessential Melbourne - a successful corporate flunky with a creative project on the side. We talked about design, art, writing. I told him about the book project, which probably wasn't a great idea: "Hey, want to hook-up? I've just written a book about sex, where I discuss all my bad experiences. Don't be scared though, I won't write about you." (To be honest, I made no such promises, as you can see by this report.)

"Um, I think I'm going to go back to my friends." he said.

I'd like to think the reason I was (nicely) rejected in this case was because my sexual and creative prowess was so intimidating. But honestly, I think it was because I was sunburned, tired and had the haunted look of a beaten dog. None of these things are attractive characteristics in a potential partner


At this point I felt like giving up.

I seriously doubted I'd ever have sex ever again; my mojo had deserted me and it felt like it would never come back. I was marooned in a country full of people with whom I had nothing in common and whose level of style and beauty I would never attain. I was over the hill: old age, decrepitude and certain death lurked just around the corner.

It's incredible what a couple of rejections can do to one's psyche. All the stuff we hate about ourselves comes bobbing to the surface like a bloated corpse. For me, it echoes my experiences of being bullied when I was a kid - the fear that deep down, I'm not good enough.

Neither of the guys who rejected me were assholes. They were both polite, honest, and respectful. Nevertheless, my psyche was ready to declare a state of emergency. I wandered a few kilometers up the beach, checked into a hotel in Canggu, lay on a deck chair on the rooftop bar, ordered half a liter of Long Island iced tea, and cried.

I figured if I had to be sad, I may as well do it in a warm place with good food and nice view.


Date #3: the Twelve-Pack

I'd been chatting to an American fitness instructor on Tinder for a day or so, but I told him I was too sunburned to meet up. I knew that one more rejection was likely to destroy my holiday. I wasn't going to take the risk.

He was pretty neat though...as we continued to talk we discovered that we had a lot of things in common. I'm an ex-personal trainer and we shared many philosophies around fitness coaching. He seemed interested in me (not just interested in whether he was going to get laid.) The turning point was when he said "Wow, you seem really cool. I think we'd have lots to talk about..." followed by a shot of himself in the gym. This guy didn't just have a six-pack, he had a twelve-pack: abs from nipples to thighs. Yep, he was definitely a legit fitness freak.

"You know what?" I said "I think I'm going to get out of bed after all. Want a drink?"

So I put my neck on the chopping block once again. My mental health was precarious at this point. If things went badly, I'd probably have to cancel my holiday and fly home.

Twelve Pack picked me up on the back of his scooter (all the local expats have one) and we chugged over to a local Canggu bar called 'Old Man'. The bar was just a thatched shack by the side of the road. It was full of tourists, but not the coiffed type; more the grungy surfers, the rockers. We pulled up stools and he ordered me a Bintang.

If I may generalize: American boys are different to Aussies. Aussies are artlessly blunt and socially awkward. Americans, on the other hand, hold the door open and always offer to buy me a drink. They have that old-fashioned respect for women that's annoyingly patriarchal but also sweet. They try to impress me by talking about themselves. I'm quiet, so a loud American can talk over me for hours. But in this case my date was so damn fascinating that I considered it a privilege to listen.

He was an ex-special-forces soldier from a dysfunctional family. He'd suffered PTSD after coming back from his tour of duty and traveled to South America to take Ayahuasca - his psychedelic experience had cured his mental health problems. Life had flattened him but he'd courageously righted himself by going his own way. He was bent but not broken; exactly the kind of guy I find interesting.

We talked for two hours. More Bintangs were consumed. At ten pm he put down his beer, swiveled towards me on his bar stool and cocked a cheeky eyebrow.

"How 'bout we get out of here?" he said.

Seeing his twelve-pack in the privacy of my hotel room was every bit as hot as I had imagined. But getting intimate wouldn't have meant as much if we hadn't spent so much time talking about the shit that really mattered.


This is why I Tinder.

Not to get straight into the pants of the first hot person I meet, but to be surprised by people, and learn from them.

When I have a bad experience I question whether I have the right to call myself a hook-up 'expert' at all. How can I give other people advice, when I fuck up too? In this case, much angst occurred because I ignored Timothy Leary's principles of 'set' and 'setting': I went on dates even though I was unstable, and I picked locations that made me feel inadequate and alienated. In this, I was responsible for my own suffering.

Luckily, I'm also capable of doing it right - having the conversations, connecting with the right people. The hardest part of dating is the courage to try again when everything seems to be going badly.

Sometimes a hook-up is everything I need: interesting, emotionally connected, sexy as fuck. It's these interludes that restore my faith in the process. Even though it's hit-and-miss, it's totally possible to have brief encounters that fulfill my needs - amazing connections that are no less valuable for being brief.

It happened because we took the time to talk before we met and because we happened to 'click' with each other when we did. As with all good hook-ups, it's that combination of good strategy and sheer luck that results in a perfect match.


The Book: read the first 50 pages




The Book: read the first 50 pages


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