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What one Englishman learnt from 2 years of online dating in New York - Part 3

 #dating #onlinedating #datingadvice #NYC #NewYork #datinglessons #datingblog #love

Lesson 3 - Wistful observations about the changing nature of human connection

So I learnt my first two big lessons in the NY dating game fairly quickly, in case you missed them they can be summarised as: 1)  that guys are mostly expected to take the initiative in dating, and 2) girls also date to get laid.

The third and final lesson I wish to impart here took somewhat longer to crystallize, and I’m still not sure I’ve quite got a firm grip on it. The first bit of the lesson might simply be: ‘life isn’t all about sex’, but the second bit of the lesson regarding what else it is about is where things get tricky, (especially when trying not to resort to any sentimental hokum that I so despise.)

These days I’ve noticed the newspapers like referring to ‘Hook-up culture’ as if it is somehow clearly distinguishable from ‘Dating culture’ and ‘Not-wanting-to-die-alone culture’. Different people in the dating scene are undoubtedly looking for a wide range of different things, but I think it’s false to proclaim that there just two sets of people and one lot are just out to get laid and the other lot are out to find life partners; there’s a whole wide spectrum between those two extremes. These days though it does seem like there is a genuine shift towards ‘living life in the moment’, and when this is combined with expectations of quick and easy gratification, and also an abundance of choice because we can meet new people easily online, of course things are going to get crazy.

I’m not sure if anyone is in a position to say if modern dating culture is ‘good’ or ‘bad’, but I think there are specific downsides that should be highlighted. One risk is that with the abundance of choice we can end up making lots of weak and transient connections with people but when things get tough and we need a genuine partner or firm friend to fall back on for emotional support then we can find ourselves all at sea.

On the flip side these days it is so much easier to find someone with compatible interests to you when you can go on a dating site where they list their interests up front! With all this choice no one should really feel stuck in a relationship they definitely don’t want to be in because they’re worried they won’t be able to find someone else....

However maybe this diverse free-market of potential dates encourages a kind of dating prescriptivism, perhaps more so amongst women, who as I’ve mentioned tend to act as the gatekeepers in this dating economy (at least to begin with). ‘I want my partner to be this, this and this’ reads someone's dating shopping list, but constructing a fictional ideal to measure partners by seems likely to serve as a kind of dream catcher for future happiness. Also is having completely compatible interests with your partner always positive? How are we going to grow as individuals if we only date people who think the same as us and do the same things as us?

If you date more people it should make it statistically more likely you will find ‘THE ONE’, or at least the ‘The ONE of SEVERAL optimal matches out of the very limited percentage of the worlds population you will encounter in your life’. Anyway if we assume ‘true love’ is a genuine thing then maybe dating around a lot does increase our chances of finding it...

But then how does one know when one is really in love? Maybe there is such a thing as ‘love at first sight’ but personally I’ve never experienced it, for me it has always been something that’s grown with getting to know someone. Sometimes you can feel the attraction growing faster with certain people, but rarely have I had long enough for that attraction to grow into a mad infatuation that I’ve called ‘love’ for lack of better word (or psychiatric diagnosis). With a culture of casual dating it might be that we don’t give love a chance to grow in any given relationship. Perhaps though that’s because we’re scared of love in the first place? Does dating lots of people actually increase your chances of accidentally skipping over a connection with the potential to develop into true love, because we're blind sided by all the ‘chemistry’ of short term attraction? Also what’s the optimal number of times you should date someone before you can safely write them off as not ‘the one’? Does one 1st date conversation in a bar actually tell you anything meaningful about who someone really is and if you can really rule them out as your soul mate?

‘Fuck knows’ is my answer to all those questions. However I think they need to be asked. We live in a world so advanced that fantasy and reality seem within a hair's breadth of each other and when the later doesn’t quite match up to the former some people decide that their reality isn’t quite good enough. If we want to actually be happy I think we need to appreciate that fantasy and reality will always be separate. It might also help to recognise the intricate and unpredictable beauty of reality that fantasy can never match. Reality might not always work out as we hope it will, but it sure as shit is a lot more interesting.

That’s the approach I’m aiming for anyway, unfortunately I’m not sure it is shared by many people in the New York dating scene. New York can be amazing (I certainly have had plenty of kinky sex), but sometimes this city makes me feel like a ghost. Strangely in this multitude of people it almost seems like human connection is just a mirage, or an illusion, conjured to manipulate people into buying or selling some part of themselves. I have had so many great dates where conversation flowed and laughs and smiles were present in abundance. However after our lips parted and my date was whisked away in a taxi or subway car it was as if a spell was broken, and again and again I was cast into a purgatory of silence and unanswered text messages. Maybe it’s just my nature as a scientist that I can’t stand absent data or unresolved questions, but those silences were the one truly awful part of New York dating that really tore me apart. If someone told me they weren’t into me it might sting for a minute if I was into them, but I can pick myself up and dust myself off, ‘I am a grown up’ as they say. With silence though your imagination is free to roam and probe at the darkest corners of your identity, it tears at your ego and claws around inside your self consciousness. Your imagination finds the absurd weak spots in your character and exploits them, making you assume painful personal deficiencies or foolish mistakes are the reason you have been left in limbo…

It is also possible that an absurdly large number of my dates were eaten by bears, or suffered other unfortunate accidents, and that’s why they never responded to my texts. However the odds of that seem small, so instead I am just left with my unanswered questions and a sense of broken connection.

I think online dating is the thin end of the wedge in this ‘the age of loneliness’; it exposes the ugly and shallow side of our natures all too easily, and highlights the diminished empathy we feel towards strangers and the low value that we place on the connections we make with people. However, I don’t think ‘hookup culture’ is the root cause. I believe that you can value people highly while still sleeping with a lot of them, and I hope my New York adventures don’t contradict this notion. Instead though I think it’s the crushing rise of ‘individualism’ that’s truly forcing us apart, and other commentators have already described this better that I could.

But what great ‘dating lesson’ am I striving towards with all this waffle about individualism? I suppose what I’m trying to say is that we should all try to assign greater value to the connections we make in our lives, whether it’s a romantic connection with a random date we meet though the internet, or a friendly connection with a work colleague, or just the person behind the counter selling us our bread and milk. Humans are social creatures at the end of the day and it’s the connections we make with each other that hold the keys to our happiness. And yes that may well sound like the sentimental hokum I was trying very hard to avoid, but that doesn’t mean it isn’t also true!

As for how to best apply this philosophy to dating without accidentally coming on too strong is still something I’m trying to figure out. Maybe over-valuing connections has sabotaged me from time to time, but then perhaps I’m over thinking things again, and maybe the best dating advice is simply this:

Find someone that makes you happy, tell them they make you happy, and if you make them happy too, try not to let them slip away.

...Oh and spank them occasionally if that’s what they’re into!

What one Englishman learnt from 2 years of online dating in New York - Part 2

Lesson 2 - Girls like sex too!

(Click here for part 1)

Shocking title huh? From the way courtship and seduction has historically been talked about anyone would think that sex is the horrible ordeal for girls, which they have to be persuaded to go through in exchange for marriage or some other righteous reward. Hopefully in this day and age most people have realised that this is hogwash and that sex can and should be a mutually gratifying experience. However what I didn’t realise until I moved to New York is that a large number of women will actually date primarily out of a desire to find good sex [1], and for them finding a relationship is a secondary ambition, or even superfluous.

Of course for women the requirements for ‘good sex’ can be significantly more stringent than they are for men. And when I say that girls are looking for good sex; they are not out looking for five minutes of awkward humping followed by ten minutes of soothing your ego. For many women looking for sex might seem like a buyers market, but it’s also a market where it’s difficult to predict whether a guy is going to be good in bed, or bad in bed... or a serial killer.

So if you’re a guy don’t get over excited by the revelation that there are girls out there looking for casual sex, it’s unlikely that a message along the lines of ‘Hey babe, wanna fuck?’ is going to cut the mustard. Projecting confidence, intelligence, and generally not sounding too much like a murderous rapist is also generally recommended.

Another thing I have learned from my New York dating spree is that apparently the presence and number of female orgasms is not an infallible metric of the quality of the sex. Some girls cum easily, some cum with difficulty, and some hardly ever cum at all (but this does not mean they don’t enjoy sex). I am also told that women experience great variability in the intensity of their orgasms and may in fact experience multiple types of orgasm, (although at present the science of orgasm defining still seems somewhat vague...)

Unfortunately for someone attempting to induce one or ten of these climaxes it seems to me that spotting when a girl achieves orgasm can also be remarkably difficult. Don’t get me wrong, it can also be really fucking obvious; if everything contracts incredibly tightly and she drenches your sheets, then that’s a pretty good sign. However everyone is different; one individual might make incredibly animalistic and orgasmic noises while she digs her nails into you so hard that they draw blood, but it still might turn out she was just having a lot of orgasm free fun. Conversely a girl might murmur quietly among the pillows and perhaps after a while her inner thigh will start to twitch a little, and so you look up and ask her if she’s close, and then find out she’s climaxed multiple times already, (but that doesn’t mean you should stop!)

So what does all this mean for someone attempting to be good at sex? I guess my advice would be ‘keep calm and carry on’... (advice that is applicable to many many things)... Is that helpful? Maybe don’t over-think sex and get desperately focused on trying to give a girl X many orgasms as quickly as possible. If you’re treating sex as a task with goals and strategies and accounts to be kept that may inhibit some of the spontaneous greatness of it. Probably the worst thing you can do if you’re sleeping with someone who has difficulty achieving orgasm is to make a big deal out of giving her one; that kind of psychological pressure is only going to make it harder and encourage her to fake it. If she feels she has to lie about that sort of thing that’s definitely going to make it harder to improve the sex life in the future. Communication and all that.

So apart from ‘keeping calm and carrying on’ what else had New York taught me about doing sex good? I would not claim that 2 years of dating has turned me into some kind of ‘sexpert’, and for me the word ‘sexpert’ inspires a kind of gag reflex born out of disdain for anyone who would be arrogant enough to call themselves by such a title [2]. In fact maybe I’m just shit at sex and no one has had the heart to tell me yet, but personally I don’t think having good sex is that hard. Just be open minded and non-judgemental, and learn to read your partner and respond appropriately, oh and try to stay in the game for a respectable length of time! [3]

The problem is that society has invented so much bizarre stigma around sex that it fuels our our collective self-consciousness, which I think disconnects us from each other. Maybe it’s all some ancient and complex plot formulated to keep the masses dissatisfied, frustrated and ‘motivated’, and maybe now this frustration helps drive our pointless materialist culture of status symbol consumption… However I digress.

Most people like sex and I everyone needs to get over this. Obviously there are dangers to it, especially if it becomes an obsessive pursuit, but perhaps people have problems putting sex in its proper place because its conventional place has been THAT TERRIBLE THING YOU SHOULD NEVER EVER DO (except when you’re married, then it’s fine for some reason...). We seem to be getting over some of the stigma around sex these days but our attitudes are very much in flux. Sometimes sex seems like THAT AMAZING THING YOU SHOULD DO ALL THE TIME AND IS ALL THAT REALLY MATTERS AND IF YOU DON’T HAVE IT A LOT YOU ARE WORTHLESS AND MIGHT AS WELL DIE. I think that as well as accepting sex we need to chill the fuck out about it. Yes, sex is bloody great, but at the end of it all you are left with are the memories, some moist sheets, and, depending on your due diligence, the chance of offspring or an STD. Similarly a lot of emphasis seems to be put on sex as the maker or breaker or human connection, as if there’s something magic about it that cements the bond between two people and if it’s not mind blowing all the time a relationship isn’t meant to be. This also seems unrealistic; sex is just a part of a much bigger picture and unlike a lot of things that might cause incompatibility between two people at least sex is something that can be improved upon and isn't always dependant on personality.

So what are specific sex skills you can improve on reading this at home? Well the best person to ask is probably the person you’re sexing, and for almost 100% of you that is not me.


Both genders seem to lose their shit about sex. I managed to turn this to my advantage when dating in New York as I set up a profile offering girls kinky fun times and it was surprisingly successful. (More details on that here). Kink is another thing that people seem to lose their shit about and all kinds of myths and fantasies completely distort the often very sane, safe, and consensual things that people actually do. A lot of folks also seem to think that having kinky fantasies is somehow ‘fucked up’ and that it reflects some deficit in the psychology of whoever has them. I believe this is total bullshit and I met a massive variety of personalities through my kink profile that I couldn’t even come close to grouping let alone labelling as one thing or another, but you can read my book and judge for yourself.

So yeah, a big thing I learned from New York is that a lot of different girls will have kinky sex with you if you just ask nicely… Well maybe not overly ‘nicely’, but if you ask them in an assured and confident way that doesn’t creep them out and make you sound like a manipulative uber jerk or serial killer. (Maybe the serial killer/uber jerk routine sometimes works as well but I didn’t want to go down that road.) Oh and having an English accent helps too.

Does New York dating sound pretty great to you now? Kinky sex here there and everywhere? Well it definitely has its moments. However the biggest lesson I learned from from dating in New York was not how to smoothly get a girl into bed, or how best to tie her arms together, or how to sext, or flog, or spank, or fuck. I spend most of my book trying to subtly establish in this lesson in the background through various rambles and tales of dating haps and mishaps, but if you’re not a fan of subtlety and just want me to spit-it-the-fuck-out-already the lesson is this:

“Man cannot live on kinky sex alone.”

And I’ll explain a bit more on what I mean by that in the next post...

Lesson 3 - Wistful observations about the changing nature of human connection.



[1] If you think that this is bad and that sexually liberated women are somehow bad people or deserving of shame, then I get the feeling we’re not going to get on.

[2] Although I think it's acceptable to call yourself a 'sexpert' if you work in the sex industry as I assume some actual knowledge is required to succeed there financially...

[3] Sure there are sexual dysfunctions, but then there are drugs and treatments for a lot of the common ones and I don’t think people should see using them as any more shameful than using aspirin when you have a headache. But still... OH THE SHAME! (To make you feel better here’s a funny story about a time I couldn’t get it up and the girl didn’t take it well...)