The White Collar Criminal

I very rarely talk about my dating life before this blog.

Partly because the last time I really actively dated was at the age of 19.

There are still a few tales which have survived the 10+ year gap.  I’ll never forget the man who brought out a calculator at the end of our date (before the days when you could at least work it out on your phone!), or the man who spoke so quietly I had to ask him to repeat everything he said at least two or three times.

However over the years, even before 30 Dates turned my encounters into household nicknames, there were men who became legends of sorts between my friends.

One such legend was the White Collar Criminal.

I was living in Whistler, Canada, working as an on-call nanny in a ski resort.  Families would call up the agency, whether they needed a babysitter for one night, or three weeks, and I’d be assigned different jobs every day – from looking after a newborn baby while his or her mum went off skiing, to watching Bond Movies on a Friday night with a group of 12 year-olds, while their parents went out for dinner.

I loved my job, and the different characters I met every day.  Some families have become friends – a number of them actually follow this blog – others became caricatures – stories I’ve told over and over in the three years since I moved back to England.

One such caricature was a family who spent their entire summer living in the penthouse suite of the Fairmont Chateau.  The Fairmont is the most expensive hotel in Whistler.  A quick Google search would suggest the family’s stay was costing them at least $2000 CAD a night.  They had been there for three months.

Over the course of a few weeks, every couple of nights I would be called up to look after the family’s children.  An extremely overweight boy of perhaps twelve, who refused to leave the apartment.  And a little girl of seven or eight, who had never been told ‘No’ by anyone.

On the second evening babysitting for the family, I met the father’s right-hand man.  It was the father’s second marriage, and his assistant explained that he had gone to school with one of the father’s older sons.


He was working in the penthouse suite for most of the evening, and when I went to order the kids pizza, as instructed, and asked if he wanted any, he suggested he take me out for dinner after the parents got back.

Working as a nanny, it’s pretty rare to find yourself being asked out while you’re at work!  Particularly when my ‘uniform’ consisted of shirts and jeans that I didn’t mind children throwing up over, and no make-up.

The Right-Hand Man was attractive, a year or two older than me (28), and seemed interesting enough, so after work, I popped home, made myself look presentable, and met up with him for dinner and drinks at one of my favourite Whistler restaurants.

Intrigued by his boss’s way of life, I began asking questions, to establish why someone would spend three months in a penthouse suite, instead of simply buying a chalet in the resort.

The Right-Hand Man explained the lifestyle he lived in the line of work he did.  He didn’t have a flat back in Vancouver – he’d been living in a hotel for years.  I began asking him everyday questions – trying to establish just how different his life sounded to any 28 year-old I’d ever met.  He couldn’t remember ever having made himself a sandwich.  He didn’t know how many times he’d flown in a helicopter.  To get from Vancouver to Whistler, most of the rich families I knew took the sea plane – a reasonably costly option which cut the drive time by half.  Instead, The Right-Hand Man had scheduled a taxi, a journey which cost three times the cost of the near-private plane.

The night ended snuggled up in his Gold-standard hotel room at the Chateau, watching Get Him to The Greek, with the RH Man teasing me about my English accent.

The next day, intrigued by the life the RH Man had described, I decided to Google both him, and his boss.

Literally HUNDREDS of law suits appeared online.

The RH Man and his boss were white collar criminals, living on the edge of the law with schemes called ‘Pumping and Dumping’ – NOT the kind you’d expect to be discussed on a dating blog!

Essentially they created false companies in a popular area, created hype, got people to invest, and then the companies would bomb, and they’d take all the investment.  (Someone reading may be able to describe this more eloquently … this was how I interpreted the crime, after chatting to an Economist Dad who I regularly babysat for!).

No wonder this guy was living a unbelievable life.

I had gone on a first date with a White Collar Criminal!

We all learn our lessons.

One of the reasons I think the process of dating is so important, is because it teaches you what you need and want in a partner.  It’s easy to look at a list of requirements and tick certain boxes.  But until you’ve experienced certain attributes or circumstances first hand, you never really know what you’re willing to tolerate, and what you’re unable to overlook.  Similarly, once you’ve been in a situation, you can come to appreciate the warning signs.

And so, with the Right Hand Man still in dating memory, a few months ago I went on a Grouper.  Regular readers will remember it – I spent the evening staring across at a table of men in Mr Fogg’s, far better suited to my group of friends than the men we’d been set up with.  One such man was Mr Mayfair – a man who had made eye-contact with me almost all evening, and who even disappeared to ‘fix his hair’ and change his shirt in order to impress me when he returned.

We exchanged numbers, and I dawdled, unsure whether to give him my surname, because I knew that one Google search, and a few clicks, would dig up every dating article I’ve ever written!  I liked him.  He was polite and attractive, he’d made a huge effort with me, and seemed charming and funny.  I’d told him about the blog, but I wanted to tell him my stories first-hand, not have him read them on here.

When I explained why I was delaying, he smiled.  ‘God, you’ve got nothing to worry about, there’s awful stuff about me online!’ His friends had said something similar earlier in the night.

That night Miss 32 and Kink and I had been celebrating the news that thanks to the 30 Dates Blog I’d be writing for both the Huffington Post and The Guardian, and when the boys had asked what I did, I’d explained I worked in banking but was gradually moving into journalism.  As Mr Mayfair bristled slightly at the mention of a journalist, I found myself regretting the intro.  There was more to this guy than met the eye.

Sure enough, a drunken Google search that night revealed a lot more to the story.  It seemed the Right-Hand Man wasn’t the only white collar criminal I’d attracted!


I have to admit, I haven’t written about it until now, because the blogger in me was hoping there would be more to the story! Mr Mayfair was clearly loaded – he’d just returned from Monaco, lived in Mayfair, and I was sure a first date would be an experience – one I was happy to embark on ‘for the sake of the blog’!

However, nothing ever came of the number swap.  For a good month or so, he’d message me about once a week.  Seeming to wait until I’d just about given up hope of meeting, and then getting in contact again.  The cat playing with a piece of yarn technique that Joe Blogs talks about in his recent insight into the reality of men and dating.

Dating is about experiences.  About working out what does and doesn’t work for you!  And learning to recognise warning signs, and appreciate when someone is being genuine.

Whilst a White Collar Criminal would certainly bring some variation to the blog … it’s not what I’m looking for in an ideal man!

So whilst I’m disappointed there were no developments on the Mr Mayfair story for you guys (a rather realistic portrayal of dating in 2014 in itself – how many phone numbers do we all get that never really go anywhere?!) I AM glad I Googled, and at least knew what I was getting into with my eyes open. (Though I do find it depressing that in this day and age you have to character reference a potential match!)

Ironically, one of the conversations I had with Mr Mayfair was about a new company I’m setting up – and he offered to do the exact thing for my company, which hundreds of articles online claimed he had defrauded other companies doing!

A lucky escape I guess!  But a cautionary tale that often there is more to a person than meets the eye …

Miss Twenty-Nine xxx


2 Comments on The White Collar Criminal

  1. Wow, crazy. Good thing you googled him. I suppose that’s the lesson, do your homework people.

    • It’s sad though isn’t it! I don’t like to know too much- I’d like to get to know someone in person and hear stories from them, but equally just goes to show you have to be slightly cautious xx

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