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

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 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.
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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:

6 Kissing Tips
Use Your Hands(01 of06)
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"It creates a physical connection in addition to your lips," says Jill Blakeway, clinic director at the YinOva Center in New York City and author of the forthcoming book Sex Again: Recharging Your Libido. "Where you put your hands isn't really all that important -- roam a little." (credit:Alamy)
Make Eye Contact(02 of06)
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"Look into his eyes as a prelude to a kiss or sometimes the whole time you're kissing," Blakeway says. "In Chinese medicine the eyes are related to an energetic pathway that surrounds the genitals." (credit:Alamy)
Vary It Up A Bit(03 of06)
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"If you've been married for a long time, it gets a little routine. You have a [certain] way of kissing and that's what your husband is expecting," Blakeway says. "Surprise him! He'll faint with amazement. Vary the pressure, the speed and the technique."Kissing when/where your partner least expects it or taking turns kissing your partner the way you'd like to be kissed are some ways to knock the routine out of your smooches. (credit:ShutterStock)
Kiss Heart To Heart(04 of06)
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"Which way you tilt your head when you kiss makes a difference," Blakeway says. "If you both tilt on your left side, lean in and embrace a little, your hearts are touching. And that's more than nice symbolism -- it's also a way to experience a deep connection because you both have an awareness of your heartbeats, which may be a little elevated because of kissing." (credit:Alamy)
Be Conscious Of What You're Doing With Your Tongue(05 of06)
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"Gently slide your tongue into your partner's mouth and then move deeper," Blakeway says. "Besides lighting up all the nerve endings in the mouth, it also stimulates the salivary glands. Believe it or not, saliva contains testosterone, and testosterone provides a little jolt to your libido. So 'swapping spit' is actually a key to activating your sex drive!" (credit:Alamy)
Kiss Longer(06 of06)
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"Kiss him longer than it takes you to sneeze," Blakeway says. "Passionate kissing is something people forget to do." (credit:ShutterStock)

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