Dating Diary 10. I’m Dating A Millionaire Who Ticks All The Boxes, But…

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So real life tossed High50‘s dating columnist Louisa Whitehead-Payne an encounter with Plane Man — minted, a mastermind, and owns his own plane. (So, Louisa, what first attracted you to the millionaire Plane Man? That he could translate old English texts, of course. Duh!). How would she get on?

We have a second date, but I have agreed to go to his house, which worries me somewhat. It will give me a chance to suss out if he is who he says he is. But I am a little nervous about meeting him there. My PA is briefed to call the cops if she doesn’t receive a text at 10:15 p.m. confirming my health and safety.

I rock up. There is a helicopter in the garden, a Porsche 911 and a Mercedes in the drive. The plot is at least two acres. The house is a bit modern and nondescript, but it has a home office, gym, cinema and a deck with a hot tub. So, unless he works for the homeowner, he is who he says he is. And he likes boys’ toys.

A delicious meal is cooked, he is charming, solicitous and, unlike a lot of successful men, does not talk about himself all night. I happily send the text at 10:15 that all is well. No kiss goodnight is attempted. OK … it’s only our second date.

Most Exciting Date Of My Life

The next invitation is to dinner on the Isle of Wight, flown in on his plane. I have dressed up and Plane Man is very complementary. So he IS interested in me physically. I was beginning to wonder. Good!

It is very exciting flying from one weeny local airfield to another. Sexy, too, with my date at the helm. We eat at a nice restaurant and I am delivered back to Oxfordshire before dark (it has to be light for private pilots to land).

It’s probably one of the most exciting dates of my life. Am I smitten? Well, I’m trying to be.

An Overnight Stay

I reciprocate by inviting him to a super-glamorous corporate do. With an overnight stay in London. One hotel room or two? Two, of course … he hasn’t even tried to kiss me yet.

I could do with flirting lessons from those horrid women on TV who make you flick your hair and do the Full Princess Diana look-up from under your fringe. Hell, I don’t even have a fringe.

Overnight London comes and goes. There is a little light hand-holding. But he does at least address the issue of why he hasn’t propositioned me. I am apparently fragile after leaving my husband so recently. Difficult to know what to say to that. Okaaay…

I decide not to say I’ve had lots of hot sex with a farmer for the last six months. Or that I am rather good in bed and like to keep my hand in. Nothing suitable springs to mind, so I remain inscrutably stand-offish. He is away for the next month but we make a soft plan to see each other on his return.

Getting My Ducks In A Row

Plane Man has indicated that he doesn’t really want a committed relationship, and I just want one person to share good times with. So I see nothing wrong with sussing out other guys, at least for the time being.

I am taking my 92-year-old ex-mother-in-law’s advice that I go out with lots of men and sleep with all of them. (Well, none of them at the moment, but I am working on that one.)

My Internetting bears fruit. I now have four dates fixed up after phone chats with four men who sound delightful on the phone. And one I have put behind my ear for later as he is on a road trip with his son in the U.S. By the miracles of Whatsapp, I get lovely funny updates from various stages of his trip.

So, the shortlist is:

1. Vice Man. Pervy? No. He is a former vice chancellor of a university.
2. Brighton Boy. Urbane ex-banker. Consulting from the seaside.
3. Guitar Man. West Country (accent not genre).
4. Home Boy. From my home town.

I know a bird in the hand might be better than four in the bush. But, frankly, serial monogamous dating might take me too long to find a suitable longer-term playmate. Parallel tracking will speed things up and I want a playmate before my looks really go south.

This doesn’t sit entirely comfortably with me. But when you are dating in your 50s, it’s a numbers game and, if you’re a woman, you need to even the odds that are against you as hard and fast as you can.

Related Articles From High50:

Brief Encounter: Meeting A Man When You Least Expect It

You Don’t Fancy Them, They’re Not Your Type Or They’re A Bit Dumb: How To Deal With A Bad Date

Stripping Off For Someone New: The Hair Downstairs Dilemma

Earlier on Huff/Post50:

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