Tag Archives: dating

On the millionaire matchmaker, and the worst date of my life
I am the opposite of The Hulk, in that apparently people really do like me when I’m angry. I know this because every now and then someone emails me a link to something unconscionably awful and says “get a load of this bullshit!”
A couple of months ago my sister emailed me to say “Have you ever seen The Millionaire Matchmaker? Honestly, watch it. You will shit a brick, then hurl that brick through the telly” – or words to that effect. As a lover of both shit telly, and having the excuse to write watching shit telly off as ‘research’, when it popped up the other day I refrained from turning over and settled myself in for a few minutes of relaxing, blood-boiling rage.
The premise of the programme is that millionaires are looking for partners. That’s basically it, although I should point out that on the one I watched all the millionaires were men and all the potential wives were women. I don’t know if this is the case for the entire show, so I’ll simply state that, naturally, if this is the case, then it’s sexist as well as offensively awful. But I’m not here today to talk about sexism, I’m here to talk about one of my biggest turn offs.
Look at all of my money!
I have a difficult relationship with wealth. Money’s great, of course. Without it I’d have nothing with which to purchase gin and crisps. But there are certain people who have a lot of money who seem to define not only themselves by it, but what your opinion of them should be. Wealth makes some people twats in the same way that good looks make some people arrogant. As if they are possessed of some magical, special quality over and above the contents of their wallet that will give them a headstart in your affections.
If you’re wealthy, then congratulations. You’re great, and you’re lucky, and you probably buy the gin in the fancy blue bottle rather than the stuff with the ‘Tesco’ logo on it. But above and beyond that, your wealth is nothing except a slightly awkward non-sequitur. If you got your money through talent, tell me about your talent. If you have it because of your background, tell me about your background. But waving fifty-pound notes and announcing your salary in a booming voice impresses me as much as a child who tells a roomful of adults that they’ve just done a poo in the potty.
The worst date I ever had
I got in trouble last week because I criticised The Rules, partly because one of them states that men should pay for things while women – save the occasional treat – should keep their purses firmly shut. Given my general hatred of discussing money, or having a guy’s wealth wafted in my face like it’s an enticing aphrodisiac, this advice reminded me of the worst date I ever had.
The gentleman arranged to meet me for a drink. This was at a time when I was pretty broke, and my weekly ‘beer’ budget was about a fiver, so I asked if we could go to a cheap pub I knew well, where I could guarantee I’d get at least one round in before I had to crack out my credit card. The cheapness was a condition of me agreeing to go on the date, and he agreed.
I arrived at the pub only to find him waiting outside, which struck me as a bit odd.
“It’s cold,” I informed him, pointlessly. “You could have waited inside with a pint.”
“I know,” he said. “But there’s a great cocktail bar around the corner and I wanted to take you there first.”
Like most Londoners, when I hear the words ‘cocktail bar’ I can’t help but picture a meat grinder, into which someone is stuffing ten pound notes. I told him again that I was quite broke, and that if possible I’d prefer to go somewhere I could afford to get a round in. After all, I explained, conversation is more important than cocktails, and I don’t really like being at the receiving end of someone’s redundant generosity.
“Sure,” he said. “Let’s have one cocktail then head back to the pub.”
Three cocktails later, I’d given up on asking. We had a couple of nice chats about his family, his job, my poor excuse for a life at the time, and were getting on relatively well. I’d managed to quell the panic that had hit me when I’d seen the prices on the menu, and relaxed into a fairly decent evening. Then we moved on. Not to the pub, because by that point he was pissed enough that all he could focus on was showing me exactly what he could buy. He hailed a taxi, which took us about 400 yards down the road, and into a wine bar which didn’t even have prices on the menu.
“What sort of wine do you like?” he asked, gesturing towards the bottom half of the menu.
“You know, I’m not really that fussy about wine,” I replied. “And if I’m honest, I’m a bit uncomfortable with you buying so many expensive things.”
A long pause, during which I shuffled nervously and tried not to look anxious.
“It’s OK – I’m not expecting anything in return,” he guffawed. “I just like nice things, and I’d like you to share them with me. We’ll have the [insert name of posh wine here].”
Until this point, I could have believed him. I could have thought – you know what? He’s a lovely guy, and isn’t deliberately trying to show off his money, he just wants to spend it. I should just suck it up, enjoy his company, and get over myself. I could have thought that, and I almost did. If he hadn’t followed the wine decision by proudly announcing:
“It’s only a hundred pounds a bottle!”
What are you trying to prove?
The moral of this story, if indeed there is one, is probably that I’m an uptight arsehole. One of the main things that made this the worst date of my life was that I couldn’t let go of the money factor.
But although my reaction might be a tiny bit extreme, the money factor is still a significant obstacle. Why? It’s not sexy: it feels suspicious. Filling my face with millionaire’s mojitos and one-hundred-pound wine is the equivalent of spending the entire date telling me that you do lots of charity work or that you don’t usually wear brown loafers. It makes me wonder what he’s trying to hide. Does he think he’s mean, so he needs to mention charity work to redress the balance? What’s wrong with brown loafers? Is there something innately shameful about ordering the house wine, or preferring pints to cocktails?
Look, if you’re minted and you want to buy champagne on your dates, that’s fine. If you love your money and want to find someone who will love it just as much as you do, that’s fine too. But that person is not me. If I’ve told you how much I hate pricey cocktail bars, then each time you buy something expensive you just demonstrate that you either haven’t listened or that you don’t care. What’s more, all I see is a huge flashing neon sign that says “I’m RICH! RICH! Fuck what else I might be, I’m RICH!”
It’s not that you can’t spend money on me if you want me to fancy you. It’s that I’ll struggle to fancy you if all I can see is your money. Put away your wallet and show me what you’ve really got.
On sex practice
So, here’s an odd statement, which the guy who emailed me was kind enough to allow me to publish:
I sometimes want to try things out – I have zero or little experience and I worry about that. Would be wrong to use a girl as just like to practise on and improve?
The word ‘practice’ bothers me, and not just because of its context-dependent spelling of ‘s’ or ‘c’. This gentleman was asking, after my article on virginity, whether it was OK to find someone to practise sexual things with (kissing, oral, and other delicious non-penis-focused activity) without having to have actual sex.
The answer to this question is a wholehearted ‘yes’, but also a wholehearted ‘no’, because of the way it was phrased.
Not having sex is totally fine
If you meet someone and want to do sexy things but without having what you’d class as ‘full sex’ (i.e. train goes in tunnel) then that is not only fine but, if the other person you’re with is a fan of kissing, oral, frotting, etc, utterly delightful. There’s a deep and gutwrenching joy in having things that aren’t ‘full sex’, and although I am personally a bit of a penetration fetishist (I find it hard to get off if I’m not being pounded, or at least under promise of being pounded in the very near future), there are hundreds of other things that are fun.
However, the word ‘practice’, makes me shudder with discomfort, because it implies some things that make me sceptical of how you actually feel about your partner.
There is no sex Olympics
The key question, really, is what are you practising for? Is there some sex competition that I didn’t know you could enter? Are there skills and techniques you need to know in order to pass a shagging exam? Is this hard work going to pay off ten years down the line when you meet someone who refuses to sleep with you unless she can see your Doctorate in lovemaking? No? Then what you’re doing isn’t practice.
It’s an uncomfortable word because usually we practise on something that isn’t the real thing. We learn to drive with supervision, in cars that have a spare set of pedals so our instructor can slam the brakes on when we almost power headlong into a roundabout (and Colin, if you’re reading this, I’m really bloody sorry). We practise exam questions on past test papers. Above all, the results of our ‘practice’ don’t really matter, because the marks aren’t real or final.
But in bed, the person you’re with is real. They have real nerve endings, real emotions and desires. To reduce them to a GCSE test paper, in which the marks (i.e. their feelings) don’t really matter sounds deeply disrespectful. This, coupled with the word ‘use’ was what gave me shudders in this guy’s email.
There’s nothing wrong with having consensual sex fun with someone that doesn’t involve penetration, but there is definitely something wrong with viewing any individual sexual partner as just a stepping stone towards the amazing sex that you’ll eventually have with someone else. Heavily implied there is ‘better’. You practice on the not-quite-real person, then have better sex with someone… well… better.
Eww.
Sex practice doesn’t make perfect
Most importantly, the idea of practice implies that if you do enough of it you’ll eventually become ‘good’. This is one of those bullshit beliefs we hold because so many advice columns, sex books, and articles about ‘Ten Ways To Blow Her Mind In Bed’ insist on peddling the myth that everyone likes the same thing. That you can be, objectively, a ‘good shag’. This – and I cannot stress this enough – is bollocks.
Sometimes you’ll have sex with someone for the first time, and loads of your trademark moves will genuinely blow their mind. They’ll sigh, and writhe, and moan in delight as you rub, lick, suck, and fuck them into a glorious and delicious climax. But this is rare. Most of the time you’ll do some things they like, some things they love, and many things that make them want to say ‘left a bit’, ‘a bit softer’, ‘no, wait, a bit harder’ until you do something exactly the way they like it.
I’ve slept with a fair few guys as well as a few girls. Each and every one of them was slightly different, with some of them doing things in ways I’d never have anticipated but turned out to love. Others did things that worked well for their previous partners but turned me right off. I’m sure the same is true of what they thought of me, and generally with those people I was with for longer, we got better at pleasing the other one and knowing what they wanted. No amount of practice can prepare you as well as the knowledge that everyone’s different. So practice doesn’t make perfect – it doesn’t even make ‘good’ – the best revision you can do is to talk to the person you’re with, and listen when they tell you what they like.
Don’t ‘use’ anyone
You don’t owe it to any hypothetical future partner to be the best you can be in bed. It’s not the case that you can pick people who don’t matter to help you perfect your techniques so that you can wow the love of your life at some point. Firstly because the love of your life may well want something completely different, secondly because whoever you’re practicing with may turn out to be the love of your life, and finally because it’s just a shitty thing to do. If I had wild and sticky sex with someone and subsequently found out that they were just ‘using’ me for ‘practice’, I’d kick them out of bed before you could say ‘I am not an unfeeling shag-robot.’
I don’t think this guy is deliberately being mean, or callous. After a few emails back and forth I think he’s just under the impression that he needs to be the best he can be. But you can be at your best not by learning techniques or practising your cunnilingus skills, but by being empathetic, caring and considerate of what your partner needs and wants. Not a hypothetical future partner – the one you’re with in exactly that moment.
On making your sexual fantasy come true
Sometimes guys ask me for my advice. Stop laughing at the back.
Although I’m as incompetent as the next person, feeling my way through sex and relationships like a horny blindfolded girl groping for the light switch, people occasionally email me and ask for help with their problems. The following predicament concerns a guy who wants to make his fantasy come true, and it struck me that there’s a theme which runs through most emails I get about this subject: whether it’s throatfucking, swinging, threesomes, or something beautifully sweet and simple like the one below, quite a few ‘how do I achieve my sexual fantasy?’ emails share a common theme. So, to try and kill a few extra birds with my stone of shoddy advice, I asked the guy for his permission to post the question, and my response.
Please chip in your own advice in the comments – I’m not an expert, and I am frequently wrong about things.
The problem: how do I make my sexual fantasy come true?
I am obsessed with girls and especially the female body. I absolutely love the female body and how it reacts to sexual stimulation.
I am 19, male and I haven’t had actual sex yet. I have been masturbating and fantasizing for several years now and really want to finally have some sexual action with a hot/cute girl. I don’t want full sex with her but I really really want to make out and pleasure her. I am very curious about how it feels for a girl and how close sexual stimulation feels with her body and words.
So as you can tell I am absolutely mullered by the fantasy of making out with and pleasuring a hot/cute girl who’s OK with not having actual sex.
The thing is: I live in a Christian community and I’m not really attractive or athletic and I don’t have a girl friend. I’m extremely introverted and so I think it’ll be while I’m in my mid or later 20s when I ‘d find a girl friend.
And my parents would wonder what I’d be doing (and against it) if I just went into town to hook up with a girl for a bit. I can’t be openly driving to people’s houses or strip clubs or whatever with my parent’s car.
So I think the best bet would be that I take a walk and have the girl pick me up while I’m doing that and us make out in the car or something like that.
But so far I haven’t found a legitimate website that I can find actual local girls to hook up with for free. I live [location redacted – somewhere rural in the US]. Do you know of any legit and free sites that will allow me to possibly find a girl willing to do this with me?
So far all I have found are scam sites and ones that I need to dumb paid membership for. And for me, I really can’t afford that risk atm. I’ve tried CraigsList but that’s all a bunch of scams..
Oh what am I to do?!?
Answer:
The good news (OK, the fantastic news) here is that what you want isn’t in any way unusual. There are lots of people who want to make out – they want the awesome touching, horny kissing, etc, but not necessarily the sex. Perhaps because they’re not ready for sex, or just because they don’t enjoy sex as much as the other parts. But I assure you, there are many people who want this. So you’re in a good position.
However, there’s a really big problem with your exact situation, and that is that you seem to want a very specific thing, and you don’t seem willing to do anything even vaguely out of your comfort zone in order to achieve it: you can’t drive anywhere, you won’t pay money, you won’t use free sites because of scams, you won’t speak to women because you’re shy. In short: your easily achievable fantasy becomes almost impossible because you need it to land directly in your lap with very little compromise or effort on your part.
If I knew what the effortless solution to your problem was, I would have bottled it, sold it, and be typing this on a gold plated laptop right now.
I don’t blame you at all – this is not my way of calling you a wanker. It seems that you are worried about so many things that all seem insurmountable. Instead of trying to overcome one, or all of these issues, you have made them conditions of your fantasy and I think that’s why you’re struggling to achieve what you want.
To sum it up, your ideal fantasy is one in which you kiss, touch, and generally have sexy fun with a girl without having penetrative sex. Big tick in that box: loads of people like doing it, so your pool of potential partners is huge. But you don’t want to have to speak to a woman much, or develop a relationship with her, because you’re shy (totally understandable, by the way: some of the guys I’ve been hottest for have been shy). You don’t want to pay for membership of a dating site (and who does? They’re pricey!). You can’t use a free site because you might end up getting scammed. You don’t want to have to drive and pick her up in case your parents find out (again, understandable, if you think that the consequences of that would be horrible for you). Basically you want all of your ideal conditions met. And that makes giving you advice almost impossible, because any advice I give would mean compromising on one of your conditions.
So, bearing that in mind, here are three advice options:
- Keep trying with free sites (I am a big fan of OKCupid, and I think you have that in the States, but if anyone else has suggestions please leave them in the comments!), and trying to weed out possible scammers wherever possible. Accept, though, that you will meet people on it who are either scamming you, who want something slightly different, who might want a relationship before makeouts, or who don’t have their own car: that’s just how humans work, and it’s impossible to recommend a site which can deliver you someone guaranteed to fill every aspect of your fantasy.
- Go pro. When I read the first half of your email it occurred to me that if you really want this specific thing, but without having to develop a relationship, then speaking to a sex worker could be ideal. Find someone in your area (on Twitter I see adultwork mentioned often by sex workers, so I’d recommend heading there first, unless any sex workers have better suggestions that they can leave in the comments, pretty please!) who you can have this experience with. This involves compromising on your ‘free’ rule, but it’s one of the simplest ways to guarantee that you can have what you’re looking for.
- If you don’t like the above ideas, then the only thing I can recommend is to compromise on the ‘shy’. Which I know I know I know is hard to do. Speak to women, and try to develop a relationship with one who would like to do this with you. You don’t necessarily have to be boyfriend and girlfriend if that’s tricky for you, it might just be a girl you get along well with who also wants to have a go at making out and touching: it’s fine. I know this is scary if you’re shy: incredibly so. But it won’t get any easier if you never do it, and if you don’t manage to find a girl who’s willing to do this with you, you may still have met some nice people and had fun with them.
And that’s it, I’m afraid: I don’t have any magic bullets. As I said originally, I’ve been asked similar questions quite a few times, and I struggle to give advice because often I think what the guy wants is for his fantasy to just happen. You’re luckier than others in that usually their fantasies are things that are a bit more niche or kinky, so their original pool of potential partners is limited by the fact that only a small slice of the population would be up for the act itself. But either way I’ve seen lots of variations of “I need X but I have to get it without doing A, B or C”. As with you, they’re all usually legitimate concerns, and understandable problems. The trouble is, when you add them all up, the only way the fantasy is actually going to happen is if a passing woman just happens to fancy making out with the stranger she’s driving past, and has the confidence to shout out of her car window and ask for it.
So, to summarise, my advice would be that you need to pick one of your conditions and either compromise on it or make some effort to overcome it, or you need to cross your fingers and hope really hard that the very unlikely happens, and do a hell of a lot of wanking in the meantime.
Oh, and worry about the car situation when you get to it.
On inappropriate acts vs romantic gestures
Once upon a time I was sitting in a tiny greasy bar with a boy, when a rose seller came along. She had a basket full of dozens of roses, each one tied up nicely and ready to be hawked to the nearest soppy romantic.
I growled my customary ‘don’t disturb me in the pub’ growl. The boy looked interested.
Romantic acts
Romantic acts don’t have to be the obvious ones: diamond rings, flowers, breakfast in bed and the like. But these things do have a certain kind of charm, and if you want to impress someone, it might be easier to reach for a bunch of flowers than a deeply personal something-or-other that has the potential to backfire.
I have a deep and sincere admiration for people who perform romantic acts. Those who know exactly when to shower love, and in exactly what quantities, to make someone melt.
But it’s not easy. One person’s romantic gesture is another’s worst nightmare, and the success of the gesture in question all comes down to how well it’s received. I was reminded of this recently when a friend told me a story about a guy she knew: madly in love with one of his friends, he journeyed the two hours it took him by train to turn up at her house. Rather than knocking on the door and sobbing his undying love directly at her, he decided to be a bit more subtle. He knew she was a chess lover, so he left two chess pieces: a king and a queen, on her doorstep, along with a dozen red roses and a letter that explained how he felt.
“Aww,” said I “how romantic.”
“Fuck that,” said she “it’s creepy as all hell.”
The roses and the romance
I hate that this is the case, but it is, and I have no idea why. Romance is a fantastic thing, and I’m sure many of us would love to have more of it in our lives. But it seems like the main thing that makes a difference between a romantic act and an inappropriate one is something the romancer can’t always know: whether your crush actually fancies you.
If they do, you’re a hero. If they don’t, you’re a loser. And possibly a creepy one at that.
I’m going to tell you two different versions of the roses story now.
Version one:
The rose seller approaches me and the boy, and my heart is beating far too quickly, hoping against hope that this shy, nerdy first date doesn’t turn into a mush-riddled disaster. All I know about this guy is his name, his occupation, and a story he’s told me about how his sister once pushed him off a swing. I don’t know him well enough to anticipate whether he’s cheesy enough to think the ‘rose for a pound on a first date’ gambit is a good idea.
He does.
Red-faced, I accept the rose. Later that evening we part, and his post-date text seems unnecessarily gushing. We never see each other again.
Version 2:
The boy grins at the rose seller, and I whisper to him “seriously, dickhead, don’t buy me a rose. I’d only have to carry it home.” He squeezes my leg under the table, looking slyly at me in the way he knows makes me want to lick him. For the last two, three, four years I’ve alternately mocked and raged at him for his lack of romance, his lack of spontaneity.
“How much for a rose?” he asks the lady with the basket. I’m looking away now, too embarrassed to make eye contact and show that, secretly, I actually really want a bloody rose, even if it’s drooping slightly and will end up getting left on the bus. She tells him how much they cost, and there’s a long silence. Ages. Aeons. Millennia pass while I stare at the rings of liquid on the bar and fiddle with the plastic twizzly gin and tonic stick and just wish he’d get on and tell her ‘no’ so that we don’t have to eke out the embarrassment.
Years, or perhaps five seconds, later, he speaks.
“I’ll take the lot.”
And he hands over note after note after note from a wallet that’s rarely opened unless it needs to be. And I walk home arm in arm with my boyfriend of many years, drowning in roses and love.
There’s no right way to do romance
Arguing with my friend over the chess incident made me sad for the boy who’d tried so hard. For his unrequited love and his inability to read the girl’s reaction. Assuming they were both in earnest, no one did anything wrong here: it’s just a misjudged gesture and a mutual tragedy. But from my friend’s point of view, it’s a stupid guy making a desperate play for a girl who’ll never want him.
As she put so succinctly: the difference between creepy and romantic often just comes down to whether they actually fancy you.
I don’t think I want this to be true.

Someone else’s story: first time sex
I love guest blogs that talk about ‘first times’, and this week’s post about first time sex is an absolutely incredible one. My favourite guest blogs usually fall into one of three categories:
- People talking about things I have no experience of.
- People disagreeing with me on something.
- People saying things that make me horny on the bus.
Today’s is firmly in the latter category. Everything about it reminds me of the excitement of meeting a stranger who you just want to squash yourself up against. This author, from A Sex Blog of Sorts, is a brand new sex blogger (you can find her on Twitter @sexblogofsorts). And as is appropriate given that it’s her first time guest blogging, she’s guest blogging about her first time. Enjoy.