My (nerve wracking) date with Britain’s pickiest singleton

We are sitting in the oak-panelled bar of a West London hotel. A bottle of chilled champagne has been ordered to calm any jitters. Before me sits an attractive brunette, ten years my junior, fixing me with a smoky, Christine Keeler-type gaze. As first dates go, this is pretty tense.

Anna Heaton is eyeing me like a rare steak she’s wondering whether to bite into. Then she takes a deep breath and begins running me through some of the recent men in her life. There have been quite few.

‘I’ve been out with City boys, a rock band drummer, all sorts really. I recently went for a drink with a racing driver who I knew it wouldn’t work out with when he ordered a pot of tea — on a Friday night!’

‘But then,’ she adds breezily, ‘I usually know whether men are right for me within ten minutes.’ Ten minutes? We’ve already been here for three. Time to chase that champagne. Anna and I are on a mid-week date, hastily arranged after she was identified this week as Britain’s pickiest singleton, following her (thus far) fruitless search for a husband.

An attractive, intelligent and good-humoured 29-year-old, Anna’s last serious relationship was two years ago. Since then, she has embarked on 77 dates (yes, 77), trying everything from blind dates and dating apps to appearing on the ITV dating show Take Me Out — all, sadly, to no avail.

She has even taken to compiling a spreadsheet, rating each of her first dates on a scale of one to 20, citing ‘looks, personality and spark’ as a way of rooting out Mr Right.

As date number 78 and, apparently, with only slightly more than five minutes left to make an impression, I begin to feel like a helpless lab rat.

Anna is dressed elegantly in a cream top, a floral patterned skirt and heels. I feel a little square in my work suit, but since Anna has previously said in an interview that she likes a man in a pink shirt, I have managed to rip one off a colleague’s back for the occasion.

‘Oh, I said that ages ago, I wasn’t really serious about that,’ says Anna. Drat. Time to roll out the big guns. Just as I am contemplating my dazzling gambit repertoire, she asks: ‘How old are you?’

Anna and Henry (pictured) on their date.  Henry said: ‘I am warming to Anna at this point. I enjoy her matter-of-fact attitude. She clearly knows what she wants — or, at the very least, what she doesn’t want’

‘I’ve just turned 39,’ I reply (note the pathetic ‘just’, like a child who says he is five-and-three-quarters).

‘Never dated anyone that old before,’ says Anna with a smirk. Crumbs, where the hell is that champagne, I wonder.

She insists that she has no prototype — no Barbie Doll Ken in mind for her Mr Right. A sense of humour is a must, she says. It would also be nice if it was someone who likes running, as she does, but otherwise she is not impressed by fast cars or any flashy accoutrements of wealth.

‘So, tell me about your last date,’ I ask. ‘What was wrong with poor old number 77?’

‘Oh he was lovely,’ she says. ‘We met on Clapham Common last Saturday. He brought along a bottle of Prosecco, I brought some plastic cups. We sat in the sun for a couple of hours chatting. We had a laugh actually.’

Someone you spent two hours laughing with? Sounds like marriage material to me.

‘Nooo,’ says Anna, pursing her lips. ‘He wasn’t good looking enough. He didn’t look anything like his photos. That’s the problem with these bloody apps.’

She’s right. Like Anna, I have spent the past two years resolutely single. In the four years since my marriage broke up, I’ve met only one person of significance. The rest of the time it’s been an endless treadmill of dead-end dates, many of them arranged via peculiar dating apps.

As Anna points out, few compare to actually meeting someone before asking them out, with some turning out to be, shall we say, not entirely as advertised. One person I arranged to meet a few months ago arrived sporting a luminous pink bob.

Anna laughs in agreement. ‘My biggest disaster was a guy who started singing a Whitney Houston song in a restaurant. We were talking about music and songs you like to sing and he belted his favourite out. Mortifying.’

Shockers aside, she readily admits to being picky: ‘I just don’t see why I should have to settle. My friends sometimes moan at me, saying I’m impatient, but it’s always ones who are in relationships themselves, wanting me to be on their level.

‘I mean, I would like to have children one day but not like some people do. I am certainly not going to marry someone just so I can have children.’

Anna Heaton who has been single for two years said: ‘Henry had clearly done his homework. I’ve said in the past that a pink shirt does wonders for me, mainly because it’s a bold colour for a man to choose and shows confidence’

That said, it hasn’t been totally hopeless. She says she did like a couple of the 77 and even went out with them a few times but they fizzled out and she can’t explain why.

‘Most of the men over the past two years have asked to see me again,’ she says sipping her champagne, which has finally — mercifully — turned up.

Ah, the second-date dilemma. I admit that I find avoiding these requests rather awkward.

‘Oh God, you don’t ghost, do you?’ she sighs in mock exasperation. (Ghost? I’m feeling my age again.)

‘Ghosting is when you just ignore somone’s messages — terrible thing to do.’ I shuffle a little uneasily. (Actually, I am a bit of a ghoster.)

‘I’m always straight with people,’ she says. ‘If I’m not interested I just reply: ‘I had a fun time but I just didn’t feel any spark between us.’

Crikey. Quite harsh, surely? ‘Not really, nearly everyone appreciates being told where they stand. I met one guy in New York and told him after 40 minutes that there was just no chemisty between us. He said: “You British are direct but I respect your honesty.” He even insisted on paying the bill, which was pretty good of him.’

I am warming to Anna at this point. I enjoy her matter-of-fact attitude. She clearly knows what she wants — or, at the very least, what she doesn’t want — and her self-confidence is beguiling. Indeed, she says her self-confidence has grown since she has been single.

 Picky Anna  wants a man to sweep her off her feet before she hits triple figures in her failed attempts to find her dream man

In her early 20s, she jumped from relationship to relationship without much time in between. When she broke up with her last boyfriend, she wanted to spend more time exploring the field and becoming more self-reliant. Appearing on a ropey show like Take Me Out in April was, she says, showing a little of her new-found exuberance.

‘A lot of my friends were surprised when they saw me on it. It was a side of me they hadn’t seen before.’

Anna certainly isn’t what I was expecting. Rather ungallantly, I pictured a terrifying hybrid of Demi Moore’s emasculating executive in Disclosure and Glenn Close’s bunny boiler in Fatal Attraction.

She can laugh about her plight, however, and is well aware of how her fussiness might seem to others. I find it hard to argue with Anna’s pickiness though; why settle for someone just for the sake of being in a relationship?

But isn’t that whole spreadsheet thing a tad extreme?

Anna’s eyes begin to dart a little tetchily. She insists that it was cooked up by colleagues at the marketing firm where she works, most of whom are in relationships.

‘You know that thing when people say they want to live vicariously through you?’ she asks. ‘It was sort of like that really.’

So is said spreadsheet currently up to date? Anna squirms. ‘No. Maybe I haven’t done the past seven. It’s on someone’s computer at work, and we gather round some mornings, filling it in. I don’t actually have access to it.’

I decide not to probe further. She’s clearly uncomfortable about how this makes her look. Still, I can’t help but wonder how I will feature in this dreaded chart.

I’ve possibly chatted a bit too much about my exes — normally a strict no-no on dates. Also, the age gap, I suspect, could be a big sticking point, while divorcés probably are not ideal to someone so young who has never been married.

It is time to wrap things up, I think. I wave away her thoughtful gesture to pay half the bill (‘I always offer’) and order a taxi to take her home. My phone tells me the cab is four minutes away. ‘Don’t worry,’ she says, smiling, ‘I think I can manage another four minutes with you.’

How generous of her. But as Anna ducks out of the London drizzle and into the car, I suspect she will soon be on to number 79.

Anna’s verdict: I would like to kiss him . . . a little bit

First impressions are everything with me, never more so than on a first date. As a dating veteran, I can confirm that the sight of a tall, dark-haired man, impeccably dressed in a well-cut suit, is an excellent start.

Henry had clearly done his homework. I’ve said in the past that a pink shirt does wonders for me, mainly because it’s a bold colour for a man to choose and shows confidence.

Henry was sporting a particularly pleasant shade of well-ironed rose. As he leaned in for a two-kisses-on-the-cheek kick-off, there was a subtle waft of expensive aftershave with pleasing undertone of attractive man. So far, so very good.

As well as the good looks, pleasant smile (I didn’t notice his teeth, I’m not a horse breeder), nice dark green eyes and well-shaven, strong jawline, those kisses struck just the right note of intimacy. Some men hug, which is acceptable only if you’ve met before. Others shake your hand, as though it’s a business meeting — awful.

Unfortunately, Henry showed his age by taking me to the sort of smart bar where the staff know you by name and keep asking whether you need anything else. It wasn’t the buzzy atmosphere I’d seek for a first date; it was a bit too quiet and had a whispery, library vibe.

It’s the kind of place where I’d be terrified that I’d break a glass. I need a bit more excitement.

Usually I date men between 28 and 35, but I didn’t mind the slight age difference apart from the slightly stuffy location.

Ground was rapidly regained when he enquired whether I would like some champagne, and also asked the waitress to ensure it was chilled — a pleasant touch.

He drank a gin martini. I’ve been on first dates with men who have drunk everything from pints to shots of Tequila, but this was a first and I thought it very James Bond. Conversation — thankfully — flowed. We talked about work, family and past relationships, which is standard box-ticking practice in this situation.

I have been much villified for my dating spreadsheet, but really, isn’t it what everyone does on a first date? We are all judging each other. A first date is a screening process.

I was very impressed by how well Henry listened to me; I once told a man the detailed plans for a family party that weekend. The following week — he’d been fortunate enough to get through my initial screening process — he had the audacity to ask what I had done at the weekend. He didn’t make it to a third date.

But Henry listened and made all the right responses. He was open, but not overly descriptive, about his past relationships — and endearingly besotted with his dog. I feel that he is perhaps looking to settle down — though not through any desperate vibe.

I know that I can’t be bothered to waste time with people I know aren’t going to go the distance.

There were even genuine laughs; at the end of the date I offered to pay half and he wouldn’t let me and then — and this is rare behaviour indeed — Henry ordered me a cab.

Did we kiss? No. I never kiss on the first date. I like to get a sense of whether I want to or not. And yes, I would like to kiss Henry — a little bit.

There has to be excitement and mystique about the second date. That’s the one where you’re standing on the edge of the precipice of a relationship and only one in five men get to that stage.

I made him say first whether he’d like to meet again and he said: ‘Yes, yes, would you like to?’

I said yes, giggled, and climbed into my taxi. Might he be the one? Well, I don’t have alarm bells ringing, so maybe.