The Tall Guy, Part 2 – Melancholy

Last time, Lucy got chatting to a lovely man from OKCupid named Simon. If you missed that, you can catch up at Part 1 – Heels.

Simon seems to tick every single one of Lucy’s boxes: he’s tall, handsome, has good hair, has a job, is clever, chatty, funny, flirty, reliable, can spell, and doesn’t have kids. In other words, a total fucking unicorn.

Question is: will there be a catch, or will he, by some miracle, turn out to be as wonderful as promised?

Lucy and Simon arrange to meet on a Thursday night. But then, a couple of days before the date a curveball arrives, in the form of Lucy’s non-monogamous part-time boyfriend Charlie. He’s unexpectedly free that evening, he tells her; would she like him to come over and give her a thoroughly good seeing-to and maybe even stay the night?

Lucy’s torn. On one hand, here is a very welcome chance to get naked with Charlie and have All The Sex – AND have their first ever sleepover. She could always tell Simon something has come up, postpone the date, and take advantage of the opportunity to get banged enthusiastically. Probably two or three times – and again the next morrning.

But what if she rearranges, and then Simon goes on a date with someone else and falls madly in love with her instead? Lucy could be passing up the chance to meet the love of her life for the sake of a quick (albeit excellent) shag.

No, she thinks. Stay strong. Eyes on the prize.

So she declines Charlie’s offer and agrees to meet Simon at Charing Cross station.

What To Wear

For a first date Lucy’d normally wear one of her many Boden* jersey dresses – comfortable, easy, not too formal, but still looking like she’s made an effort. Tonight, though, she’s determined to pull out all the stops to wow Simon, so she puts on a figure-hugging dark green pencil dress and tops if off with a slash of scarlet lipstick. It’s her lucky outfit: last time she wore it, to a friend’s birthday party, she ended up snogging the host’s brother. So the dress has form – let’s hope it works like a charm tonight.

But then there’s the question of shoes. Four times, yes FOUR, Simon asked Lucy to wear high heels to their date. He says it’s because he’s self-conscious about being tall, an explanation that Lucy suspects may, in fact, be what psychologists refer to as utter bullshit. In reality, it’s probably just a thinly-veiled attempt to satisfy some sort of weird shoe fetish – or worse, hide a controlling personality.

So what should she do? Should she stubbornly ignore his request, just to prove she won’t be ordered about by any man (unless, of course, they’re both naked), or should she wear heels in case his paranoia is genuine?

Snarky, don’t-fuck-with-me Lucy would normally go for option (a), but she likes Simon, and she wants to look good, and her heeled ankle boots go very nicely with this dress. It’s not capitulating, she justifies to herself as she zips them up, because he’s probably hoping for 4-inch stilettos, which she doesn’t even own. So suck on that, Simon!

First Look

He’s waiting outside the station for her. Tall, slim, handsome, with a full head of steel-grey hair, wearing jeans with a shirt and a suit jacket, and proper shoes with actual socks (proving that he’s not a complete animal). He seems smart and approachable, and Lucy likes the look of him immediately.

But as she leans in to kiss him on the cheek she gets a waft of aftershave so toxic it makes her eyes water like a leaky gutter. Somewhere between surface cleaner and anti-freeze, the smell gets right inside her sinuses and activates her gag reflex more effectively than the thought of Boris Johnson naked. Fuck.

This assault on her olfactory nerve jolts her back to Kenya, last year, when she first met Brad and the incredible scent of him made her want to drop her knickers there and then. It’s astounding what a difference smell can make, she thinks in wonder, taking a step back from Simon and trying to breathe through her mouth.

“You look amazing,” he tells her, and Lucy smiles awkwardly. He really is very nice, but what the fuck is she going to do about the fact that the smell of him makes her want to vom?


At Simon’s suggestion they head for the bar of the Charing Cross hotel, where a woman with a clipboard asks if they’re there ‘for the event’. Lucy has no fucking clue what she’s talking about, but briefly wonders if they should chance it and say yes anyway. Maybe there’s free booze at this event. Maybe there are hot guys with better taste in fragrance?

But Simon gets in there first, with a “No, sorry,” and Lucy feels a twinge of disappointment.

They find a table in the bar and order cocktails. Simon doesn’t say much – he seems quiet and lacking in confidence; the charismatic joker from his WhatsApp messages nowhere to be seen. There’s an awkward tension in the air – possibly caused by nerves, or the weight of too much expectation. Maybe he’ll relax after a drink or two, Lucy thinks hopefully.

“I’m sorry I made you come to Charing Cross,” he tells her.
“I did notice that!” she laughs. “But it’s fine! Do you live south then?”

Simon tells her he lives out in the sticks near Sevenoaks.
“Why there?”
“It’s near where I work.”
“And what do you do?”

He works in IT, he tells her. He fell into the job straight out of school – he didn’t go to university – and has worked for the same small company for the last 20 years.

“I think maybe it’s time I moved on,” he tells her dejectedly, “but I don’t know where I’d go. I’m probably too old now anyway, y’know. I feel so middle aged, I can’t compete with all these hotshot young things; they won’t want to hire an old git like me…”

This downtrodden version of Simon is nothing like the sparky chap Lucy knows from WhatsApp. He seems tired and defeated, which makes her feel rather sad for him. Probably not the reaction he was hoping to get, TBF.

Not that she doesn’t sympathise – because of course she does. Life can be tough and it’s hard being on your own. But this is a date – they’re supposed to be having a laugh. She’s supposed to want to lean in and kiss him, not give him a hug and the phone number of a good therapist.

She wonders if Simon’s lack of confidence has anything to do with not having been to university. Lucy’s not a snob about education per se – she’s met plenty of people with degrees who are Olympic-level morons, and plenty without who are among the most brilliant go-getters she’s ever met, so she knows a degree is not the be-all-and-end-all. But there does seem to be a correlation between further education and confidence – as though three years of getting pissed in student union bars and writing the occasional essay somehow give a man a sense of his place in the world, a certain sense of pride which the guys who haven’t been through those formative years seem to lack. So while she certainly wouldn’t rule out a guy without a degree, she does seem to prefer them. Because confidence, as we all know, is sexier than Tom Hiddleston in a three-piece suit carrying a plate of chocolate cake.


Pep talk

She tries to cheer him up a little. “You’re not middle aged!”
“I’m 43,” Simon says sadly, rebuffing her efforts with determination.
Lucy fights back. “That’s only three years older than me, and I’m definitely not middle aged. Being middle aged is a state of mind, and I’m simply not ready for that. I still get pissed on a Tuesday night and wear skinny jeans and dresses with trainers… and if you say you’re middle aged then so am I, and I’m Not Having That!”
“Oh I couldn’t wear t-shirts and trainers any more!”

Lucy’s valiant efforts to lighten the mood are falling on deaf ears. There’s just something a bit gloomy and beaten down about Simon that’s casting a massive fucking downer on the entire proceedings. She can almost see him fading away into middle-age invisibility before her very eyes. But if age really is a state of mind then it’s definitely Simon’s attitude that’s ageing him, not his date of birth.

Not to be defeated, Lucy redoubles her efforts to brighten him up.

“Of course you can wear trainers! You can wear whatever you like!”
“Well maybe I should have a cool makeover. Get an earring and a tattoo too!” he jokes, cracking a smile for the first time.
“Sure, get a tattoo,” encourages Lucy, “but definitely not an earring. Earrings on men are bloody terrible.”
“All the girls say that,” says Simon sadly, sounding like a little boy who’s just been told Father Christmas isn’t real.

Lucy tries to make up for having just crushed his dreams. “You really don’t look middle aged,” she says. You could definitely pass for 38. And you have great hair and you’re really slim. No middle aged spread there!”
“What do you mean? I’m a bit fat. I need to work out more.”

Lucy heaves an internal sigh louder than her neighbours’ kids yelling at each other at 11 pm on a Monday. FFS man, lighten up!

She’s still hoping the sarcastic and funny version of Simon she met on WhatsApp will put in an appearance soon. Maybe a second drink will help bring Fun Simon out from wherever he’s been hiding.


Opening Up

Over another round of cocktails they get chatting about their past relationships. Simon tells her his longest lasted two years, but that was a while ago.

“It’s hard to meet women these days,” he tells her. Most women my age either have kids or want them, and I don’t. I never have, I just find them really boring. I have a nephew, and that’s quite enough for me.”

It’s as though Simon is quoting directly from Lucy’s own head. Hallelujah! A man who feels the same way about children as she does! Maybe he could be perfect after all, if he would just cheer the fuck up a bit…

“What about you?” he asks.

Lucy tells him about The Ex, and about how she’s been single for four years.
“It amazes me that you’re single, a beautiful woman like you,” he tells her.

She shifts uncomfortably and pretends not to have heard the compliment. “Well I feel like I missed the boat. I was in a serious relationship from age 30-36, which is when most people settle down. Everyone else got married while I was with the wrong guy.”

Without warning a wave of sadness crashes over her and begins to spill out of her eyes. Fuck’s sake! Is this the alcohol making her weepy, or is Simon infecting her with his negativity?

Fork In The Road

They finish their drinks and Simon suggests going for a wander along the Strand to get some dinner. It’s a nice offer, but Lucy’s unsure. He seems sweet, but sparks are hardly flying between them, and his low energy is putting a serious downer on the evening. Plus there’s the small matter of the repellant aftershave. Maybe she should just cut her losses now and not drag the pain out any longer.

She wonders whether Charlie’s still available. Perhaps this evening can still be salvaged some other way…

And yet. Simon seemed more promising than anyone has in a really fucking long time, and she’s not sure she’s ready to admit defeat. Maybe he’s nervous. Maybe he’s only gloomy because he hasn’t met her yet – after all, Lucy’s hardly one to judge someone for feeling a bit negative from time to time. Perhaps they are each what the other needs to put joy back in their lives.

Also, and probably more importantly, she’s hungry.

While she tries to make up her mind, she goes to the loo and texts Charlie. Ever reliable, he immediately replies saying he’s now made other plans, which makes Lucy feel even sadder. She realises she’d been hoping he’d be free to step in at her hour of need and console her in yet another dating disappointment, but instead, she’s only ended up doubly disappointed.

So OK, dinner it is. She goes back to give Simon the good news and discovers he’s paid the bar bill.

Fuck. Now she feels guilty too. Jesus Christ.


A short walk up the road they find a small tapas restaurant – all dark wood paneling and candlelight. It feels charming and cosy: the perfect venue for a romantic date. Though obviously this date is fast becoming less romantic than a trip to the STI clinic.

They’re squeezed into a small corner table, at right angles to each other, knees almost touching. It’s a little too close for comfort, and as she’s done so often before Lucy’s forced to slide as far away from Simon as possible. She realises she’s hoping he doesn’t do anything forward like try to press his knee against hers or touch her hand, and then feels another wash of disappointment that her skin isn’t prickling with the sort of desire she’d been hoping for when she optimistically squeezed into her pencil dress.

FFS! she thinks. Why don’t I fancy him? He’s nice!

They order a selection of small plates to share – pork belly, meatballs, salt cod, patatas bravas – and manage to agree with no difficulty at all. Well that’s a win, she thinks, clutching bravely at straws like a drowning man clinging to a lifebelt.

“So I saw from your photos that you like travelling,” says Simon. “Where’s the coolest place you’ve been?”
Lucy tells him about her recent four-month trip to Kenya. “What about you?” she asks.
“Oh I don’t travel,” he states baldly. I’m too much of a workaholic. And I worry too much about work when I’m away to enjoy it. I only take ten days’ holiday a year, over Christmas, and even that I only do because they make me.”

Lucy’s absolutely horrified. A man who doesn’t like going on holiday? Is that even a thing? All hopes that Simon might be The One finally vanish like the bar tab at a work drinks event.

She lapses into stunned silence.

Digging a hole

“So, what have you got planned for the weekend?” asks Simon, clearly running out of conversation now.

Lucy, who never has anything planned with her weekends because her friends are mostly fucking married with kids and spend their Saturdays and Sundays at farm parks and playgrounds, says she’s pretty free.
“Oh! We should do something!” announces Simon enthusiastically.

Lucy hesitates for just a fraction too long. “Yeah!” she manages unconvincingly. “Maybe!”

But that extra second’s delay has given the game away. Simon rushes to backtrack. “Oh… Ha! Maybe not then! That’s me told!”

Lucy cringes and tries to save her face and Simon’s feelings. “No, no!” she garbles, embarrassed. “It’s not like that, it’s just that I have a lot to do. You know, errands, and writing, and I was planning to go to the cinema…”

But it’s too late. Once again Lucy’s complete inability to act or lie in any way has proven to be her downfall.


They split the bill and head back to the tube station.

“It was lovely to meet you,” says Simon. “Let me know you got home safe. Not that I think you won’t make it. Why do we even say that?”
“Maybe women are less likely to make it home than men. Or maybe it’s just the patriarchy speaking. Are you oppressing me?” Lucy grins, trying to break the awkwardness.
“Well it’s hard for us men,” Simon laments. “We can’t get it right!” He smiles, gives her a kiss on the cheek (during which Lucy tries not to breathe in the toxic aftershave), and walks away.

As Lucy makes her way through the tube station she feels another huge wave of sadness wash over her and tears again start tingling at the corners of her eyes. She had such high hopes for this one, she really did. He seemed so great. So why was there no chemistry? Why did he just make her feel sad, instead of happy? Why didn’t he make her laugh? Why did he smell so wrong?

Good as her word, she messages to let him know when she gets home.

Oh fuck. Why did he have to send such a sweet message? Now Lucy feels even worse. He’s a nice guy, so why doesn’t she fancy him?

But maybe she’s been doing it all wrong. Maybe instant chemistry is not the answer. Maybe, if she gives him a chance, he’ll grow on her. Maybe he’ll be more cheerful next time. Maybe she can train him to like travelling. Maybe she can save him from getting an ear piercing.

And so, determined not to give up on the first decent guy she’s met in, like, fucking forever, she decides to give Simon a second chance.

Next time: Will a second date change Lucy’s mind about Simon?

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  1. ckav86
    8th June 2019 / 7:46 pm

    Oh dear. It’s a no from me, I’m afraid. No point in meeting him again, you’re only leading him on unnecessarily and he’s not at all the kind of fella I’d imagine you’d go for. Men who whine and steadily refuse to put their best foot forward on a first date are disrespectful to you and to themselves! What a dud.

    • Lucy
      12th June 2019 / 10:18 am

      You’re probably right, but I had such high hopes for this one I’m really not ready to give up just yet! What if he grows on me? He probably won’t, but I need to give him a chance!

  2. 9th June 2019 / 6:43 pm

    How tall is he?
    Remember you and high heels and and…
    I hope he stops draining and becomes as fun as when he texts…
    Like you didn’t meet Charlie for him common!!!
    All the best…

    • Lucy
      12th June 2019 / 10:17 am

      He said he was 6’3 but might have been a touch taller. And yes, I’m hoping the funny side comes out next time!

  3. Nick
    9th June 2019 / 8:22 pm

    Bit harsh from CKAV86 but they have a point about Simon not being your type. He sounds a bit like ‘Tim Nice-But-Dim’ but maybe not quite as dim.
    The real question though Lucy is do you see yourself with a guy from Sevenoaks who has worked in IT for the same small firm for 20 years and has never travelled (unless you count Charing Cross as travelling)?
    That said, Wonderwall springs to mind, though you will be doing the saving.

    • Lucy
      12th June 2019 / 10:16 am

      Hi Nick. No, I’m afraid I don’t really see myself ending up with someone so quiet and unadventurous. But all the guys who are more my type are taken, so what can I do? Maybe I need to force myself to think outside the box…

  4. Sophie
    11th June 2019 / 7:23 am

    Lucy, it is so sweet of you to keep the conversation positive and give him a second chance, even though he does not seem very deserving. Hopefully he steps up on the second date !

    • Lucy
      12th June 2019 / 10:15 am

      Thanks Sophie! He was a nice guy and I felt sorry for him. I also wasn’t ready to give up on him just yet because he ticked a lot of boxes. So yes, let’s hope all the people who say you don’t need to have an instant spark are right!

    • B
      14th June 2019 / 10:59 pm

      ‘She wonders if Simon’s lack of confidence has anything to do with not having been to university. Lucy’s not a snob about education per se’ …… but you clearly are, and it’s screamingly evident from the way you word this. It’s a sweeping generalisation and you should be utterly ashamed of yourself

      • Lucy
        15th June 2019 / 11:54 am

        Mate. Breathe, calm down, wipe the froth from your mouth and then read the entire paragraph.
        I’ve dated men with and without much education. It has never worked out – usually because they have so much insecurity about me being better educated. As I quite clearly said, it’s about confidence, not education.

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Names and some minor details have been changed to protect the innocent. And sometimes the guilty.
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