The Entrepreneur

Since things didn’t work out with Pardeep the Separated Dad, and since Lucy is still out of work and looking for fun excuses to put on actual clothes and venture into the outside world, she’s logged back into Guardian Soulmates to see if any other interesting-looking guys have messaged her.

It’s fairly slim pickings.  She’s got a few ‘likes’ and a small handful of emails, but most of them have profiles that are at best lazy and generic and at worse completely horrifying.  Going on a date with one of these guys just so that she can speak to a real human being for the first time in several days seems like the height of lunacy. After all, who knows if they are even human anyway?

There’s only one who looks remotely interesting.  Bill is six feet tall, slim, with a good head of brown hair, a reasonably good-looking face, and glasses that make him look intelligent and a bit cute in a geeky way. Since Lucy’s last four proper boyfriends have all been geeks with brown hair and glasses, Bill clearly fits the type.  On top of this, in his profile he clearly states that he (a) is not a hipster (a definite plus after Lucy’s experience with Malcolm) (b) has never sported a beard (hurrah!) and (c) is looking for a confident, independent, intelligent woman.  Sounds like he and Lucy could be a perfect match!  (Yay!)

But as always, there are a couple of potential catches.  Firstly, Bill is 48.  That’s a full ten years older than Lucy, and Lucy can’t help wondering if it’s Too Bloody Old.   She objects not only on the grounds that almost-fifty does seem pretty ancient to a woman who still deludedly thinks of herself as being in her mid-30s, but also because as a matter of principle she’s pissed off with the way it seems to be socially acceptable for pervy older guys to chase after much younger girls.   She often comes across 40-year-olds on dating sites who state they want to date women under 35, which royally pisses her off because Lucy would like to date a man her own fucking age, but it appears she can’t because they are all chasing after younger totty and consider her to be too fucking old, and as a result she may be forced to settle for some crusty pensioner who left it too late to settle down, has finally decided he’d like kids, and is hoping a woman in her late 30s might be just desperate enough for a baby to let him knock her up.  Which, of course, Lucy isn’t.

So no, on principle she should refuse to date Bill, because she definitely does not want to perpetuate the notion that self-satisfied older guys can happily aim for women 10 years younger and actually get them.

And yet… Michael the Married Man, with whom Lucy pretty much fell in love, was also 48.  She’d never have guessed: he looked about 43 or 44, and he definitely didn’t sound or act much older than her (except when he occasionally referred self-deprecatingly to his advanced old age) but the fact remains that if she’d spotted him on a dating site, she might have rejected him and missed out.  And who knows, maybe Bill could be the new Michael, except without the added complication of a wife?

The second thing that causes her to hesitate is the fact that, in the box for job title, Bill has put ‘entrepreneur’.  Lucy thinks this makes him sound like a complete twat. What does ‘entrepreneur’ mean anyway?  Is he trying to sound intriguing, independent, and loaded?  Is he trying to suggest that he’s his own boss, runs his own business, and is raking it in?  Lucy thinks it’s more likely that he’s the struggling ‘CEO’ of an ill-advised startup with just a single employee (himself) and a bank balance redder than a group of Labour party members eating strawberries on a hot summer’s day with no suncream on.

Nevertheless she decides, as always, to give him a chance.  In the end, she thinks, it’s all about chemistry, and if they meet and sparks fly faster than a rocket on Bonfire Night, then she won’t care about his age or the fact that he’s a bit of a pretentious knob.   So she accepts his invitation for a drink, and since Bill is his own boss and can therefore give himself the afternoon off, and Lucy is still ‘between contracts’ (aka funemployed) they agree to meet at 5.30 pm on a Friday afternoon in Notting Hill Gate, in a pub that Lucy suggests since Bill doesn’t usually hang out in West London.

Lucy wouldn’t normally dream of doing a first date on a Friday, but decides it’s ok because it’s just a late afternoon drink, so if Bill turns out to be a prize dickhead she can tell him she has exciting Friday night plans she needs to dash off to.  She doesn’t, of course – in reality she’ll be heading home as speedily as possible to put her pyjamas back on and crank the heating up – but Bill doesn’t need to know that.

At 5.35 precisely she exits the tube and makes her way to the Mall Tavern, a cosy gastropub just a few minutes walk away.  Since she’s a little late, she’s fully expecting Bill to be waiting by the bar, or to have grabbed a table, but instead she’s surprised to see he’s waiting outside, even though it’s the middle of fucking winter and cold enough to freeze the tits off the Venus de Milo.

She sizes him up as she walks towards him.  Doesn’t look as tall as she was expecting – could he possibly have rounded up an inch or two?  Very slim build too, so the overall impression is not as big and imposing as she’d hoped. Looks like his photos though… so on balance the final result is not a resounding no, but not an enthusiastic yes either.  All still to play for, she thinks.

“Hey,” she says as she approaches, and leans in for a kiss on the cheek.
He goes for two, the French way. “Mwah… mwah,” he says as he does so.  Not a kissing noise, but the actual word (if it’s a word) mwah, as if he’s channelling the character of Eddie from Absolutely Fabulous.
Lucy’s not sure what to make of a 48-year-old man who air kisses like the caricature of a 1990s PR girl, but she’s pretty certain it’s not a good look.

“Why are you outside?” she asks.  “It’s freezing!”
“Oh, it’s too noisy in there,” he replies, rather disdainfully.  “I thought we should go somewhere else.”
Lucy looks longingly in through the window at the drinkers inside in the warm, cosy pub.  It really doesn’t look all that busy, and she’d been very much looking forward to a glass of wine in a convivial atmosphere.  She’s also miffed that Bill has turned up his nose at her choice of venue after making her do the choosing, but he’s already made up his mind, so there’s nothing she can do but go along with it.

“So what then? Do you want me to suggest another pub? Or something else?  A coffee?”
Lucy’s already not feeling good vibes from this date, and is beginning to think a quick coffee might actually be the better option, so she’s relieved when Bill agrees and they head round the corner to a cafe on Notting Hill Gate.

There’s a sign in the doorway telling them to ‘wait here to be seated’, so despite the fact that the place is almost completely empty, they stand by the sign like mindless fuckwits waiting for someone to notice them and show them to a table.  Which takes what feels like about four hours, during which Lucy can’t think of a single thing to say, nor make eye contact.

As if to fill the silence, Bill takes off his coat. Underneath he’s wearing blue jeans and a fine knit black polo-neck jumper.  He seems to be precisely channelling Steve Jobs under some misguided notion that this is what you have to wear if you want to be considered a successful entrepreneur.  But Lucy thinks he looks like a middle aged nerd trying to be cool, which is not normally the type she goes for.

Finally the waitress shows them to one of the many empty tables and takes their order.  By now Lucy is more than ready to dive into a large glass of wine – she’s realised she’s going to need it to get through the next hour – but before she can get the words out Bill raises his hand, almost as if to silence her, and says, “I’ll just have a tea, thanks.”
Can Lucy really order wine when her date is having tea? It seems a bit awkward to do that – and besides she’s not sure there’s much point if she’s just going to go straight home afterwards. So she decides to order tea too.

She wonders why he’s not drinking – maybe he doesn’t drink at all?  Lucy’s not sure she could date a teetotaller.  She’s not a raging alcoholic or anything, but she does like wine and cocktails very much, and the idea of dating someone who might sit there, po-faced, judging her as she polishes off a whole bottle of sauvignon blanc by herself sounds pretty tedious to say the least.  She’d better find out to be sure.

“Do you not drink?”
“Oh I do,” he replies, ‘But I’m going out after this, so I need to pace myself.”
“Oh, where are you off to?”
“I’m going to meet some friends to play board games,” he reveals proudly.
Yawn, thinks Lucy.  Playing board games is not at all her idea of a good way to spend a Friday night.  But she tries to feign interest anyway, if only to keep the conversation going.
“Oh really? What board games?”
“Scrabble and chess, mostly.”
Sounds riveting.  Of course it’s always possible that Bill and his friends are planning on getting wasted and playing strip scrabble before ending up partner-swapping, but somehow she seriously doubts it.  Or at least, she hopes that if he is he’s not intending to take her along as his partner.
“Have you tried scrabble speed dating?” she asks.  “It’s a new thing where instead of just speed dating, you play scrabble as you move around.  I haven’t been but I’ve heard it might be good fun, or at least not as completely horrific as regular speed dating.”
“Actually no, I haven’t,” Bill replies.  “But I’m very good at scrabble.  I know All The Words, so they’d probably hate me there.”

Lucy thinks there’s a good chance that if the girls at the event dislike Bill, it’ll be less because of his champion scrabble skills and more because he’s turning out to be a self-satisfied prick.

The waitress returns with two individual pots of tea, accompanied not by a cup as you might expect, but by a small, heavy round bowl, like a cup except the pretentious hipster version.
There is silence between them as they concentrate on the pouring and stirring.  Lucy reaches for the milk, but as she’s just about to take it Bill grabs it from under her fingertips and pours his first.  Lucy withdraws her hand in surprise and watches as he makes a big show of carefully pouring the milk into the cup first, and then the tea afterwards.

She wonders if the fact that he does milk first, and not tea first, means they are fundamentally incompatible.

“These bowls are odd,” she says, to break the silence.
“I think it’s a French thing,” Bill explains.  “I used to live in France and I remember having them then.”
“I lived in Paris for a while,” Lucy tells him, hoping this mutual common ground might spark more of a conversation.  “But I didn’t like it much.  I’m not sure I’m cut out to be French: I adore croissants but I don’t like red wine or blue cheese.”
“Oh I love cheese, especially Roquefort,” Bill reveals, as though it’s a huge achievement.  “Do you not like any cheese?”
“I like hard cheese, like cheddar, but not blue cheese, which I think is basically overpriced mould.”
“I never used to eat much cheddar,” Bill reveals.  “I always thought it was too basic.”

Too basic? What, not fancy enough for him? SMH, she thinks.

“Yeah,” he goes on, “I was surprised to discover it’s actually quite nice, and I was amazed to see how many different types they have in the supermarket.”
“I know,” Lucy agrees, now warming up to a medal-winning chat performance.  “It’s like there’s one section for all the other cheeses, and a whole section for cheddar, different strengths, grated, not grated – but who buys ready grated cheese FFS?!  And then actual brands like Cathedral City and that other one that I can’t remember.”
“So what sort do you buy?”
“It’s hard to find the right one. There’s too much choice. And it often comes in big blocks and then I don’t eat it before it goes furry…”

Lucy’s really struggling to keep the conversation afloat now, and frankly can’t quite believe she’s somehow ended up having an in-depth debate about fucking cheese on a first date.

The subject entirely exhausted, Lucy tries to think of another topic.
“So what do you actually do?” she asks.
“I’m an entrepreneur,” he reveals, entirely unhelpfully.
Lucy tries not to let him see her rolling her eyes.  “Yes, you said that in your profile. What does it actually mean?”
“I run a software company.”
“Oh. So you do IT then.”

Bill looks slightly affronted.  “Well basically I come up with ideas, inventions if you like, and then I make them happen.
So he’s an inventor now? Inventor AND entrepreneur?  No wonder he’s so proud of himself.
“So what have you invented,” she asks?
“Well we created this brilliant software for use in banking, but I sold that. Now I’m doing online shopping software.  Next I might write a book.  I have so many ideas I don’t know what to do with them all. And so many books that get published are terrible.  I read this one book the other day, that was just so rubbish.  It was about how to turn your ideas into reality.  And I thought to myself, I can write this book better than this author has done, so maybe I will.”

“…” says Lucy.

She doesn’t know how to engage Bill any more. Clearly he’s only interested in one person, and it’s not her.  But she still has half a pot of tea to drink, so she bravely carries on regardless, chatting now just to fill the silence and get to the end of the date without too much awkwardness.

“I have ideas occasionally,” Lucy tells him, “but I never know what to do with them.  “I had an idea for a TV show once, and then six months later the exact same programme was on the telly.  I’ve also had ideas for a couple of apps, for example a dating app, but I wouldn’t have the first idea where to begin.  But maybe I should find a friendly app developer and try… maybe I could invent the next Tinder and become a millionaire!”  She laughs awkwardly.
“Oh you won’t make any money from apps,” says Bill, disparagingly.
“…” says Lucy again.

Lucy finishes her tea.  Bill still has quite a lot more left in his cup, and Lucy is unsure what to do. Should she order more out of politeness, and for something to do while he finishes his, sip by excruciating sip?  But she really doesn’t want to commit to another pot, and is afraid if she does so then he will order another too, and the whole trauma will go on until the End of Fucking Time.
She decides to wait for him to drink up, and wonders exactly how long that will take.  Her mind begins to wander to the rest of the evening ahead, and what she might have for dinner. There’s a Tesco between here and the tube station; maybe she will nip in there on the way home and get a Finest Pizza.   Mmmm, pizza…
She wonders how long it will be before she go home and fill her face with All The Carbs and (basic) cheese.

“So what are you up to this weekend?” Bill asks.
Ah, thinks Lucy. There it is, the big flashing sign that says we’re all out of conversation now.   When someone asks ‘what are you up to this weekend’, or ‘so how have you been finding dating’, you know there definitely won’t be a second date.
Lucy tells him she’s going to a Christening party thing tomorrow, and on Sunday she’s meeting a friend. And by friend, she means a date.  She sincerely hopes it’s going to be a better date than this one.
“What about you?” she asks him.
“I’m in a concert tomorrow night.  I sing in a choir.”
Lucy sings in a choir too, so at last here is something they have in common.  “Oh?” she asks, “which one?”
“Well actually I’m in lots of choirs, not just one.  I’m good, and there are never enough men, they’re always crying out for good tenors, so I’m on all the mailing lists.  Then they just email me saying do I want to sing in this or that concert and I just pick the ones I think sound good.  I don’t really go to rehearsals, I just turn up and sing.”
Of course you do, thinks Lucy.  Wouldn’t have expected any different.

She wonders if Bill is trying to impress her, or if he really is just as much of a self-satisfied prick as he comes across.  She has a feeling it’s the latter: he really doesn’t seem to be making any effort to impress her, and why would he when they have absolutely zero chemistry.

Finally, thank God, he finishes his tea.
“Right. I’d better go off to meet my friend,” he says.
Thank fuck for that. Clearly he’s as entirely underwhelmed by this date as she is.  Lucy is deeply relieved.

Outside the cafe, they pause.   Lucy pretends she is going the other way so she doesn’t have to walk back to the tube station with him and do awkward goodbyes there.   He kisses her on both cheeks.  “Mwah, mwah,” he says again.  Lucy has to work really hard to stop herself from laughing. Or just punching him in the face.

She walks away, and then hides round the corner until he’s gone before heading to Tesco. There she buys eggs, English muffins and smoked salmon so she can treat herself to Saturday brunch tomorrow, and a Tesco Finest ready meal for her dinner tonight.
You can tell Lucy is a glamorous girl-about-town because she buys Tesco Finest, not just regular Tesco meals like the common folk eat.

Then this glamorous girl-about-town goes home on a Friday night to put her pyjamas back on, crank the heating up, and enjoy her rock’n’roll Friday night in front of the telly.



  1. 7th April 2018 / 3:12 pm

    This was a really funny read.

    I’m sorry he turned out to be so pretentious, but that does make for funnier reading, no?

    I look forward to reading more.

    • Lucy
      7th April 2018 / 8:28 pm

      Well yes I suppose it does, though the aim is actually to find someone. Being able to write a good story is just the silver lining ot the cloud when the date doesn’t work out…
      Thank you for taking the time to comment! x

  2. 8th July 2018 / 9:25 am

    All the best Lucy. Welcome to Kenya!

    • Lucy
      8th July 2018 / 3:06 pm

      Thank you you very much!

  3. 16th September 2018 / 12:29 pm

    It’s a fine line between arrogance and confidence. He seemed to be a smart guy and you potentially had a lot in common but when someone loves to tell you how smart they are I always switch off. “Ohh I’m a Dr in this.. I’m a fellow of that” I always want to get to know the person, not how smart they are…. I don’t date peoples CV…

    • Lucy
      29th September 2018 / 10:36 am

      Hi James! Thanks for the comment and sorry for the slow reply, your comment ended up in my spam folder for some reason! Yes you are absolutely right, confidence is sexy but when people start showing off, bragging and name dropping, it’s a massive turn off. I think some guys treat dates like a job interview, they think you’ll be impressed if they list all their achievements, but really all I want to know on the first date is: do we have chemistry, are you a nice guy, and do we have a laugh together?

  4. 14th November 2018 / 2:36 pm

    … that was funny.
    You are funny.
    Am picking my way thru all of your stuff now…your textathon with Ben hooked me.
    Wished I’d have blogged all my dates now ( I was a founder member of all dating sites back in 2003 ) … way way over a 100 dates; bit different in those early days cos common perception was that all men on there were axe murderers… but as we know, they were made to gravitate to POF so girls knew where they were.
    I did blog one of ’em on my site “’ … it might amuse you. Or not.
    Hope you bought and are enjoying some of that cheaper wine I tweeted you about recently.
    Cheers……. Neil

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