28 dates on 28 different dating sites. What could go wrong?

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28 Dates Later by Willard Foxton: Part Nineteen, the New York Millionaire

In which Willard discovers his inner gold-digger.

One-way ticket to paradise. Photograph: Getty Images

Now that I'm 2/3rds of the way through this experiment, I've realised something strange has happened to me. Whereas three months ago I was a complete online dating virgin, after 19 dates on 19 dating sites, I'm now regarded as something of a dating expert. I frequently get requests from friends to review their profiles, help them write messages and so on.

Leaving aside the ludicrousness of this as a proposition - I mean, if I was an expert at dating surely I'd have a girlfriend by now - it means I do have to sometimes give brutal advice. This has included having to type the phrases "I think women are scared off by the fact you dress like a Miami pimp" and "I'm afraid I think your messages display the sort of charm you'd expect from a Nazi propagandist".

That said, I have also seen some people with messages, pictures and profiles which seem perfectly attractive to me, where the person in question doesn't seem to be having much luck. One of these people - a very successful lady in New York - rather depressingly told me "My girlfriends looking at my profile think I come across as too strong and too smart." Too strong and too smart? Neither of those seem like negatives to me.

Indeed, my ideal woman would be strong and smart. My sort of idealised life in my mid forties would include me at home, writing brilliantly incisive columns in the morning, then cooking something from Observer Food Monthly in the afternoon for when the kids get home from school, before my high powered, strong smart wife gets home from her incredibly responsible, well paid job. Then, of course, we'd have a row about why I hadn't done the hoovering or something, but hopefully my excuse of "But I had to tell the nation how bad the Labour party are!" would placate her.

As a writer who's a good cook, I've sort of unconsciously been building myself towards being the ideal stay at home dad for some time. The problem is finding the sort of woman who's in the market for a creative househusband. And that's where millionairematch.com comes in.

I'd always assumed that millionaire dating sites were either places for sexually inadequate JP Morgan Partners to meet gold-digging bimbos (step forward Sugar Daddy dating, Miss Travel and Meet Wealthy Men) or are transparent fakes, trying to leech bank details out of wealthy men in the guise of a "wealth verification process". All of these sites encourage UGLY RICH MEN to register to find BEAUTIFUL POOR WOMEN.

Sugar Daddie

It's got a pretty seedy feel to it; especially Miss Travel feels like a site where you swap sex for airline tickets. The site specifically bans escorts - because swapping money for sex is sordid, but selling your body for a flight to New York is A-Ok. Unfortunately, being neither a rich man, nor a beautiful woman (not, lets face it, a beautiful man) I don't think any of these sites were for me.

That said, I had been intrigued by millionairematch - mostly because a friend, a barrister, had met her fiance on it. In her words, she was "sick of being taken out in Birmingham, and fancied being taken out in Barbados". She'd heard it was a good place for successful women to meet successful men, had registered on the site, and within a year was engaged to a lovely, handsome vice-president at a private bank. So, armed with the knowledge that it was real, I registered on the site & got to work.

One of the strangest things about this website is that the rich person has to verify their income, and you pick your income from a drop-down menu, before it gets verified. There's a screenshot of the menu below - my favourite option being the "Yes, I am the heir to a large fortune".

Millionaire date value

I imagine the verification process for that involves sending in pictures of your skin tight chinos and telling the site the name of your polo pony.

If you get verified as rich, you get a diamond next to your name, and you are allowed to upload pictures of your fabulous wealth. This is the most horribly gauche end of the site, with people uploading huge amounts of pictures of their shiny trucks, massive yachts big villas, and tiny cocks mountains of shoes. It's not a website I'd recommend to anyone who is easily outraged by a copy of FT How to Spend It or an issue of Tatler.

Millionaire

Men with massive trucks.

It's surprising how readily women on there respond to messages; although I do think I stood out by not being posed on the roof of my truck, pouring Cristal on myself. Indeed, my biggest problem was less finding a date, and more finding a date in London whose diary matched up with mine.

Eventually, after around a month of messaging one lady, she told me she was going to be transiting through Heathrow, and we arranged to meet for dinner in the Gordon Ramsay restaurant in Terminal 5. That's past security, so I bought myself a £10 one way ticket to Frankfurt so I could get into the restaurant. Sad long experience of missing flights for work (and occasionally pounding on the pressure door of aircraft, begging the crews to let me in) told me that missing the plane, even after missing the last call, wouldn't cause a security crisis.

So, anyway, I sat down on the ugly leather chairs, and waited for my date. I was proper excited - she was very charming by message, and, I'm not going to lie, I was excited by how minted she was. She arrived, bang on time, and was stunning. She was beautifully turned out, despite a full day at work, and was wearing an assortment of tasteful - yet doubtless incredibly valuable - jewellery. I suppose I wouldn't have sat trying to guess the value of my date's clothes had it not been a date off millionairematch, but there you go. I am a shameless gold-digger.

We got to talking, and she had a wonderfully blunt way of talking. It's not uncommon in people who work in the fund industry, but it was still hilarious to hear that manner of speaking transposed into dating chat. For example, she explained the failure of her first marriage by nodding gently, fixing me with a steely blue gaze and saying "Vegas Hooker orgy", with no further explanation. We had a few acquaintances in New York (take your pick, it's a small world, finance, or it's a small world, Jews), got to talking about work stuff relatively quickly. We talked a lot about business and politics; unusually for someone in finance, she was a Democrat, and so being left-wing in the US made her politically about the same as me.

We talked about the states, she told me about some terrible dates in New York ("He took me to his parents on the second date. He hadn't told them I wasn't orthodox. Cue lecture.") I told her a few hair-raising tales of travelling around the deep south, which she found hilarious. Before the date had really started, her flight was called, and it was over. She insisted on picking up the cheque (smile "I'm the millionaire, remember?"), and has since invited me to a dinner party in New York.

Of course, I'm paying my own way…