Introduction
The dissolution of my marriage set me free to date others, and one of the significant ways you can discover life after a divorce is to start dating again. So, I did just that!
As a freshly single woman, I wasted no time jumping into the dating saddle. The only problem was that I had no idea how to ride or guide myself through a problematic dating scene that is the norm in a modern and digital world.
Firstly, I had to navigate online dating websites and all the extra hassles from dating online.
After I got the hang of it, I was faced with needing to research my way through profiles and talk to all these men seeking my attention.
Knowing nothing about them in advance was a headache. The people I generally matched with were dating failures, to say the least.
Truth be told, it's easier to manage escort bookings dates with a deposit than it is to organise real-life dates from flakey people on online dating sites.
In this blog, I reveal one of the worst dates I have ever been on. Unfortunately, digital romance fooled me into one wacky date that I shall never forget.
I take you through how online dating works for freshly divorced readers and bring you up to date with the risks of online dating too.
From there, I will tell you a romantic story of how I got off by getting out of the dating scene for a while to become the other woman in a whirlwind affair.
Lastly, I detail my first steps into escorting as a career, including a recount of my first booking.
This is part two of my personal story series about how I became an escort. If you haven't read part one, do that first by clicking here.
Please note that some names and locations have been changed in this story for anonymity and privacy reasons.
So, are you ready to discover life after divorce and online dating in the modern world? Let's start!
Discovering Life After Divorce
My ex-husband and I were married for ten years and were friends before we got together long term.
After taking some time to pack, move and heal, I was excited at the thought of dating.
Well, truth be told, I was excited to have a lot of sex, but dating was how I would get it.
I didn't want a relationship and was perfectly happy with being on my own.
Dating seemed like an alien world to me, and online dating was like another universe to navigate through.
For a while, there I was out of my depth, up the creek without a paddle. In the thick of an online world, I was not accustomed to it at all.
My Experience Online Dating
During my brief stint at online dating, I noticed that many men I encountered had an entitled and appalling online demeanour.
Some of the men I met either didn't know what they wanted from online dating or lied about their situation and expectations.
I encountered a handful of men who openly assured me that what I wanted, a sexual relationship, was not all I was going to get. Instead, they wanted to bed and then wed me.
One even expected me to be a supportive parent to his children I hadn't even met.
I guess I was kind of a catch. I had a great job and my own property. I wasn't emotionally needy or seeking out a relationship of any sort.
After a few bad dating experiences, I decided to take a different path and approach.
First, I paid more attention to details to weed out the bad from the good. One weed did, however, creep through into my ranks in the most surprising of ways.
Only a few months into my newly acquired single woman vibe, I experienced one of the weirdest dates I think I have ever been on.
Meeting Daniel The Wordsmith
Daniel was a wordsmith. He knew how to get my attention and maintain it from the first moment I matched with him online.
When he wrote to me, it was like reading poetry.
I wanted to be naked with him inside me for a night.
Danial claimed to be a Perth based actor, and to me, he seemed well versed by the way he wrote those naughty emails that landed in my inbox each day
It was almost as if seductive words dripped right out of his mouth and rolled sweetly off his tongue.
I could only imagine what other lovely treats his tongue could do to me too.
Also, recently divorced, I felt a connection almost immediately. He was relatable and honest. His openness and rawness put my mind instantly at ease.
I took my time getting to know him over a month or two before agreeing to meet for a fateful first date in Perth.
Dating Failure
After taking off from Melbourne, I landed in Perth for a one-night stopover. I was there, I had landed, and I was ready to rip my skirt off.
We only had one night for a glorious and fun-filled first date. I was expecting a steamy rendezvous. But, our first dinner date was nothing short of disastrous.
He wasn't like the man who had wooed me online at all.
Physically he resembled the images he sent, but the way he spoke about himself, other women and his work concerned me.
He didn't seem as in-depth or eloquent as the person who was emailing me.
During dinner, Daniel spoke mainly of the time spent working on his new bachelor pad, the musical he would be in and how he spent his afternoons at a fancy local health club.
He didn't gloss over or skip any revolting details about how the hot, young ladies who worked there found him attractive.
He complained about the cost of dinner and female expectations on dates.
He spoke to me in parrot language and assured me his parrot understood him in conversation.
Let's just say. It was a quick dinner. I decided to call it a night and escape.
Returning back to my room, I was confused by his change in demeanour. I made the mistake of making concessions for his behaviour change.
Perhaps he was nervous.
Perhaps he just needs a bit of time to be himself.
Our emails continued as usual until we met again for my next stop a few weeks later.
"I have the most romantic and steamiest date" in mind, Daniel said.
"It's so hot, and you will want to take your clothes off straight away."
This revived enthusiasm gave me renewed confidence in his potential as a future lover.
But, I was not prepared at all for what was waiting for me once I touched down again.
I wonder if you can guess what he had in mind.
Dating Daniel Take Two
He met me outside my hotel, filled with excitement. His energy was buzzing like a child who discovered all the unwrapped presents under the tree on Christmas day morning.
"So lovely to see you again," he said, revealing a bouquet of beautiful roses hidden behind his arm.
"You shouldn't have,' I replied.
"They are simply beautiful, and what a pleasant surprise".
He led me to an uber ride, and we jumped inside.
We were on the way.
Then it dawned on me that I didn't know where that was.
"Where are we going?" I asked.
"You will see," Daniel said.
I most certainly can't unsee even to this day.
The uber arrived at this steamy destination.
Daniel jumped out of the car and whisked around to open my door.
Where on Earth was I?
The uber door closed, and the car sped off.
Hang on! Is that a local pool he is walking me towards?
The Steam Room Debacle
I can not express how uncomfortable this next part was or why anyone would consider this a horny, fun date.
Daniel's "health club" he had talked up so much on our previous date was, in fact, a local pool.
Our second date was to be in the male steam room for the afternoon.
Instead of enjoying a wild and naked filled sex romp, I was bearing witness to the bare naked men in the filthy steam facility in the middle of nowhere.
One was picking his nose.
Another was picking his toes.
All ten of the men enjoying the steam looked puzzled as to why I was there.
To be frank, I couldn't understand why I was there either.
"Are you going to take your towel off?" Daniel asked me.
I could feel the eyes of the other men staring at me intently with anticipated delight.
"Perhaps, we can go somewhere else, more private instead," I asked.
I was secretly hoping for an immediate escape from this unsexy encounter.
Somewhere Private?
Daniel lived down the road from the local pool, and I agreed to follow him there for the afternoon.
By this stage, I felt the time and effort already invested might be worth it if he was at least good in bed.He had one last chance in my mind to make an outstanding impression.
He didn't fail on the impression, but we didn't make it past first base.
When we arrived at his abode, I was impressed. It was a beautiful suburban house with a luscious green garden wrapped around a stunning wooden verandah deck.We started walking down the garden path towards the house. But we walked around the side and towards the back, to my surprise.
At the end of the path was a small granny flat out the back of what I soon found out to be his mother's house. Worst of all, she was baking a meal inside.
I started to get flashes in my mind of cult killer movies. You know the ones where families lure women to their house of doom?
Inside his flat was a mess.
A lounge covered in bird poo and a vast, golden birdcage took up most of the space. Inside was some exotic looking bird I had never seen before.
It started chatting to us as we got closer, and Daniel squeaked back at it.
Oh-yeah. Daniel speaks parrot, remember? How on Earth could I forget that.
Mother Daniel came to stand by my side as I stood at the doorway of the flat.
"You must be Olivia?" She said while giving me an unexpected hug. She continued speaking while holding me in her tight grip.
"I wasn't sure if Daniel was going to let us meet his new girlfriend today. But, I am glad to see you here."
I'm sorry, what? I have to get out of here!
Escape was in the forefront and flashing through my mind. My heartbeat increased, anxiety flooded every inch of my body.
I accepted her overly long and friendly hug without a word, then watched her walk back inside.
Daniel was sitting on the bird poop covered couch and ushered me to sit by his side. He asked me if I could rehearse lines with him for his upcoming role in a new musical at the high school he taught at sometimes.
"I'm sorry, Daniel. But, unfortunately, I have to leave," I said.
The look of despair was written all over his face.
I am a pretty honest person and told him I was uncomfortable. I told him that we were not girlfriend and boyfriend.
I wasn't cruel, but I was factual in my delivery, and I said we likely were not destined to meet again soon.
He walked me to my uber and watched it leave as he waved goodbye.
The Aftershock
When I got back to my room, I was in shock.
I tried to account for the day over a cup of tea that I quickly replaced with a glass of red wine.
What the fuck just happened?
Indeed there is a mistake, and I am dating the wrong guy. The man who sent the emails is nothing like him at all. The thought did cross my mind, and I wonder if it was his mother writing to me.
I opened my laptop to look over the previous messages we sent, and waiting for me was a new email from Daniel.
I opened it, and immediately my heart skipped a beat, but for all the wrong reasons.
He felt rejected, and he didn't hold back in violently describing to me how much he now despised me for wasting his time.
He thought I had broken his heart by being deceptive towards him, and as a result, he was in misery.
Wait a minute?! How in the world was I the deceptive one?
I didn't respond, but the whole thing made me uncomfortable. So I took my profile offline and settled for some quality masturbation over the next few months.
If you are considering online dating, make sure you keep reading for all the information they don't tell you when you sign up and start swiping right or left.
What Is Online Dating?
Online dating services are websites and mobile applications that claim to help you meet people.
Important to note that "meet" carries different interpretations and holds weight across varying demographics.
The younger crowd tend to attribute applications like Tinder to be a vessel for casual sex and hookups with zero repercussions.
Websites like Eharmony, Ok-Cupid and Match claim to use advanced technology to help you meet your future partner.
From cheaters to fetish daters and setting up your first time fuck, there will undoubtedly be a site or application that proclaims it will solve your dating, intimacy and companionship needs.
There are online dating websites that cater to all kinds and for all walks of life. So no matter who you want to meet, you likely can online.
Why Do We Use Online Dating?
As many as one-in-three people are dating online or using dating applications worldwide.
Fifteen per cent of the Australian adult population is now using Tinder, making Australians the number one user of this dating application globally.
People turn to online dating for a variety of reasons.
One in ten or thirteen per cent are simply looking for sex, which was precisely why I decided to go online and mingle as a new and horny single.
Forty-eight per cent do it just for fun.
\While others might seek out and look for more meaningful relationships.
What Is Online Dating Like?
"Frustrating. Life-changing. Overrated. Exciting. Terrifying. New."
These are only a few words of many by women who are new and back in the game with online dating after a divorce.
From my experience, I concluded that online dating is an overwhelming minefield that delivers underwhelming results.
Many people lie on their profiles about their location, name, age and anything else they wish to lie about. One online dater sent unsolicited pictures of their penis wearing a sunhat to my inbox as soon as we matched. Showering me verbal abuse for not appreciating the creative effort.
Yes, the weird and the wacky are plentiful when it comes to online dating.
The online world has opened up many opportunities to date and meet people you might never have encountered before, or so you are led to believe.
Tinder Algorithm Limits Your Dating Pool
Tinder and Hinge take the cake or superficial dating at a fast pace. But do you know how their algorithm works?
Some online dating profiles match you with others to meet based on answers to profile questions. But Tinder is different.
The system is called ELO, and it's similar to ranking systems that determine the skill levels of professional chess players.
Since 2019, Tinder has evolved the standard ELO algorithm, which only assessed your looks and location, to now include your previous history of swipes and how often you use the app as a determining factor in your profile desirability.
You are only given the option to see users with similar "desirability" scores, and you only get so many.
When nearing the end of your assigned pool, the algorithm will recycle profiles of those you didn't like the first time.
Yes, this includes people you have unmatched with previously.
Those potential matches with similar scores in your area are all you get, and you get them on repeat like a dating app groundhog day.
Ouch!
Tips For Online Dating After Divorce?
Dating, in general, is like groundhog day.
Plenty of men and women online don't say what they want and don't mean what they say.
Do not jump too quickly into online dating when you are still grieving. I think personal and physical interactions are more beneficial and safer for you to do.
Beware if you proceed with online dating. There are many liars, groomers, creeps and catfish just waiting for a heartbroken and vulnerable man or woman like you.
Don't disclose too much information. Publicly connect or display your social media accounts or contact details. Don't be silly and pay someone any money that you have never met in a romance scam.
I would like to remind my readers that you need to assess each person you meet online for potential dates.
Be careful how much information you give others.
You never know who is on the other end, gathering all that information about you.
Dangerous Liaisons and Online Dating Hazards
Having concerns about online dating are well-founded. You would be a silly sausage indeed if you had none.Over fifty-five per cent of online daters experience an online or physical problem/ threat while dating online.
Fifteen percent of women who use online dating reported conversations that made them uncomfortable, just like the gent who sent me a sunny prospecting pic of his sombrero-wearing penis that hurt my eyes.
Nineteen percent of women reported high occurrences of threats about physical harm, compared to only nine per cent of men.
Men seldom expressed concerns about their personal safety while partaking in online dating or using dating apps.
But, whether male or female, straight or single, you need to know about the potential risks involved and how to avoid them when online dating goes wrong.
Keep Your Information Safe
Online dating users are twice as likely to experience a cyber security incident compared to those who do not partake in dating online. Why is this?
People who use and access online services more often always show a higher vulnerability to security events than others who do not.
More time online equates to more potential risks online.
This is because of our complacency, increased availability, online visibility and unwanted leakage of personal data.
Tinder users are excessively willing to disclose information without realising it.
"You are lured into giving away all this information... Apps such as Tinder are taking advantage of a simple emotional phenomenon; we can't feel data. This is why seeing everything printed strikes you. We are physical creatures. We need materiality."
Luke Stark, a digital technology sociologist at Dartmouth University
Men Take More Risks
Men put themselves at risk more than women online by disclosing too much information about themselves when appealing to potential lovers.
Thirteen percent of men reported phishing emails that claimed to be from an online dating site, when only seven per cent of women reported the same.
I think it's easy to understand why this is the case.
In the physical world, women are already suspicious of new people around them who know their information and how someone contacts them.
Unfortunately, as a woman, we have to be on guard to protect ourselves from those who might want to do us harm.
This does tend to translate into thinking about our safety online as well.
On the other hand, men are not susceptible to as much violence or risk.
Instead, men feel the need to capture women's attention by disclosing too much information about where they are, who they work for and how much they earn.
Come on, guys - you're not a peacock, put those feathers away!
Giving away too much information about yourself online can lead to not so great people paying attention or targeting you directly.
Spyware, Malware and Ransomware
Twice as many male online daters said their device have been infected with malware, spyware or ransomware.
With nineteen percent of business owners who use online dating apps have had their device infected with malware or ransomware.
Data Breach
It's not only potential catfishing scammers speaking with you online that you need to be aware of at all times. The company, website and applications you use are also at risk of being hacked and hijacked too.
In July 2015, the user database of Ashley Madison was stolen when the commercial website prized itself on enabling extramarital affairs was hacked.
The hack reported that over 32 million records from users slipped into the hands of those who intended to acquire them for nefarious deeds.
A dataset that was almost tailor-made for sextortion.
Sextortion And Blackmail
The advantage of sexual blackmail is that it is unlikely to be reported. But, unfortunately, this makes the victim an easier target to ensure a payoff for scammers and hackers alike.
In 2020 the Ashley Madison data breach reared its head again online, with millions of people being emailed and blackmailed over the content directly taken from the original hack.
Online and digital security is only the tip of an enormous iceberg underneath a raging sea.
Sexual Assault and Physical Abuse.
"In all of those [apps], there are people out there with predatory behaviour looking for other people to meet and assault," Jill Maxwell from Sexual Assault Support Service
Dating apps have been under increased scrutiny for their role in facilitating harassment and abuse. Yet, just as divorce is on the rise, so is the use of online dating services.
Physiological Abuse And Stress
An Australian study of dating-platform messages revealed that sexist abuse and harassment disproportionately affect women targeted by straight men in 2018.
Tinder and similar apps fail to adequately address issues of online harm. Currently, users mostly aren't protected beyond the screening measures each platform chooses to implement.
Rejection Violence
Women are more likely to experience abuse from men when partaking in online dating.
Rejection violence is exactly what I had experienced from Daniel, the wordsmith in my first few months of online dating. Another few months had passed since then, and I was aching to have some fun. My hand was tired, and my mind was bored, So, I tried a different approach again.
This time I started searching to meet only older men with money, and this is how I came to be on Seeking Arrangements for a short time.
What Is Seeking Arrangements?
Seeking Arrangements is similar to online dating websites like Eharmony and Ok-Cupid, but it has a twist. The aim of this website is to connect wealthy men with women for semi-paid arrangements, or what is commonly referred to as Sugaring.
Sugaring or Sugar Daddy/Sugar Baby is technically sex work, but I was not aware of this at the time. My intention of using this site was to match and meet men who didn't want strings, and they could keep their money. I was in it for the hot and steamy, carefree sex.
Only after a few weeks of being on Seeking Arrangements did I find what I wanted most.
The Other Woman
Leo was a married Australian businessman who was seeking fun with a lady but scared of any strings that could ruin his marriage. He had his shit sorted, no expectations of looking after children, his work times were flexible, and his dating time with me was too.
Leo and I saw each other for well over a year with not a single issue at all. I was happy to be the other woman in a non-emotional affair. In return, I was frequently doted on sexually.
Needless to say, I was a happy and sexually fulfilled woman, but like all things that are good, all good things must come to an end.
One night, one of the last times Leo and I were together. He spoke to me about seeing escorts from time to time.
“You would have an amazing time doing that," he said.
At the time, I didn't know whether to be offended or flattered by the comparison.
Either way, the thought stayed in my head for weeks until one day, I decided to give it a go. I mean, why not? I have sex to give. Men want sex and will pay for it. The shortcut in my brain was I get to have sex, and I got paid. Woo hoo!!
Researching Sex Work
I started researching sex work in Australia, and I came to the realisation that it was legal here. Because I am originally from Canada, I just assumed it's illegal everywhere like it was in my home country.
Yes, I was totally stigmatising when I first started researching the topic.
The idea that sex work was a criminal act or offence was the part that made me not think it a legitimate option for me.
The stigma for me was that it was a criminal act. Once I realised it was actually really legal, it was like, oh my God, this would be a great extra earner.
I thought I could do this on my weeks back from work abroad. I could smash repayments on my mortgage.
I could retire earlier than I thought and lead a naughty life that no one would know about.
Getting Online
I had got myself some naughty pictures and started fiddling around with online escort directories. With my ads up, I was overrun with more booking enquiries than I could handle or account for.
No penis sombreros picture, though… Surely escorts get messages from the Penis sombreros guy?
I was hesitant to accept the bookings coming my way and found myself highly picky to the point I didn't know who to say yes to.
What was going on in my mind is rather difficult to explain. I was hesitant of jumping into the deep end as an escort because I made a lot of assumptions about who was contacting me and why.
Even though I had done the research and discovered that working wasn't a criminal act in Victoria, I still had reservations about the kinds of people who might book escorts.
I was worried I would be hurt, murdered, stalked or just plain harmed in any way
I can admit now that I was deeply misguided in my beliefs, and although many sex workers are mistreated by clients, managers, peers and society all the same. My encounters so far have been fantastic. I cherish this experience and hope to continue making it a part of my best life.
In addition to my troublesome beliefs, my disastrous date with Daniel and the abuse he sent after was etched clearly into my brain; it was an experience I had trouble trying to shake.
Nonetheless, my first job was booked, we were locked in, and I was going to his house that night.
That's when the nerves and the doubt started to creep in. I had finally got to this point, and now it was coming to the crunch, and although I was excited, I was somewhat scared too.
Could I actually be an escort?
Was I able to do this?
What was he really like?
What did I do if I didn't like him?
What was I doing?
Olivia - what are you doing!!!
My First Job
The questions continued to flow through my brain in the hours leading up to my first job.
My gosh, I have never been so nervous before in all my life.
Still, I got ready, and when it was time to go, I put on my big girl stockings and heels.
Looking in the mirror, I reassured myself.
"You got this, sexy lady. You got this!".
I didn't believe a word that the sexy lady in the mirror said to me, but off I went anyway to prove her right.
When I arrived at his apartment, my hands were trembling.
It was as if I had lived three lives of time passing from when I pushed the buzzer and when he said: "hi! come inside".
Walking up to the elevator, I reassured my frantic brain that he likely didn't speak parrot, and even if he did, it was something I knew I could contain or maintain.
All of a sudden, I was at his door, and he didn't waste any time. It was slightly ajar as I stepped up to the outside. I didn't get a second to pause from my walk up the hallway...
"Olivia," he said. "Come inside, and you are more than welcome here. Can I offer you something to drink?"
"Absolutely!" I replied, walking through the door as I listened to the latch click behind me and then I was there.
This was it!
"You look terrified," Allen commented on the obviously nervous and girlish smirk across my face.
"Oh no, not me", I returned with a giggle. "Just a tad nervous as it's my first time."
Allen was delighted.
He took my hand and caressed it with anticipated delight.
We sat for a while in his decadent lounge drinking wine and sharing war stories from online dating, ex-partners and alike.
Once at ease, I wanted to have him, and I wanted him to have me.
It had been some time since my sexual dalliance. I was eager to feel wanted and adored and to do the same to Allen. But, equally, I longed to please and be pleased.
I was buzzing with excitement.
He leaned in and kissed me, and I could taste him. He did taste good. All of a sudden, my body was electric with hormonal ecstasy. So, what happened next?
Well, I don't kiss and tell all the details. But, the rest is history, and that is my story of how I became Olivia Winsome.
How I became me!
