Dating: A man’s perspective – by John Doe

Today I have a guest post. It’s from a male friend of mine who prefers to remain anonymous but I was really thrilled when he offered to write it for me, partly because I love his writing but also because I thought it would be interesting to get a man’s perspective of dating. I may not be throwing myself back on the market any soon but it’s still all useful research.

He did suggest that I might like to split it into two posts but honestly it’s so easy to read that I thought you would prefer it all in one go. Enjoy!

Dating for men

After planning our ‘big day’ investing time, care and – yes – money into an endeavour that now seems faintly ludicrous; I found myself spat out of the other end of the relationship sausage machine; shrink wrapped with a ‘Divorced…’ red sticker slapped across my cellophane.

I think there is a belief that the recently separated man will go on a gonad numbing shag-a-thon, Tindering his way through every available woman he can match with like a modern day Viking. I must admit, the temptation is there – there is no shortage of available and willing women – but alas I am cut from a different cloth and I like my relationships to be meaningful. So what’s a stereotype-busting man to do?
The first thing that happens – after a reasonably respectful mourning period – is that I was subtly (and not so subtly) introduced to single, female friends, friends of friends and other tenuously connected ladies. This is incredibly awkward. One feels obliged to like them – like eating your children’s cupcakes – but you are thinking a couple of things:
  • They probably know my history – maybe better than me – and they have already (probably…definitely) formed an opinion of me.
  • If we do get together and it doesn’t work out (for whatever reason) then I will have to inquire about the guest list of every social engagement for ever, until I die, to avoid awkward moments. Or leave the country.

So, as a general rule, I subtly (and not so subtly) avoided these introductions. Mainly for the above reasons but also, importantly,  my friend’s view that they were ‘pretty’ or ‘gorgeous’ rarely correlated with my opinion of what constituted ‘pretty’ or ‘gorgeous.’  These introductions were almost exclusively arranged by my female friends.

So, what is a 42 year old man to do next? Hang out in bars and pick up women? Really? Does that even happen any more? Do I even know a bar where that would even be an ‘thing’? I have been married for 8 years and spent the 2nd half of that time (seemingly) watching box-sets, walking around shopping centres and not having sex. So I categorically do not know bars like this.

So, you go online. I felt a bit weird about it at first, because it almost felt like an admission of failure: that I couldn’t, in the traditional sense, get myself a date by other means but I soon got over this as it is a perception rather than a reality.

I used Tinder and OKCupid – firstly for ease of use and secondly they are free. I didn’t want to pay a dating site. A lot of them want to you pay for 3 or 6 months up front and I simply didn’t want to do that – feels like a weird form of prostitution. These apps basically base all your decisions upon photos. Are they hot or not? – put simply. It feels brutal – totally carnal – to judge people purely on their looks but I figure: I would do the same in a bar, so why not here?

After I put in my criteria (no one under 35 and no one over 47) I guess I found 40% attractive enough to say yes to. My final figure I matched with was 37 women (on Tinder). I messaged about 10 women on OKCupid and EVERY SINGLE ONE of my matches on Tinder. I got 9 replies on Tinder and 4 on OKCupid.  I got a bit indignant at first  – why the hell didn’t they message back? Why are they so rude? But I came to realise (and learnt from women who were dating) that women really hold all the cards at this stage and they can be as picky as they want because their match to message ratio is way, way higher. That’s the bald truth – but there you have it.

Then you start chatting. I would say that the number one question asked was: how tall are you? Luckily I am 6’2” so I passed muster – but God help me if I were 5’6”. I would then be asked what I do. I lost two because I wasn’t an investment banker / hedge fund manager / CEO etc. You know what? Good. Like I need another woman obsessed with money.

I lost another because I told a joke that she didn’t find funny – it was about dating and I thought it was funny (BTW the joke is: finding decent men online is like looking for parking spaces; all the good ones have gone and the only ones left are either too short, too tight or too far away…). So I am down to 6 on Tinder and OKCupid is notorious for how slowly people respond to messages.

The important thing is to set up a date quickly because otherwise you end up having a ‘textual’ relationship and this can get serious and you (or her) might get disappointed when you finally meet. I do, however,  give women my full name so they can stalk me a bit and ensure that I am legit and not a nutter as there are many, many nutters out there. A girl I know told me about setting up a meet with a guy who turned out to not be the 6’0” slice of honed muscle she was expecting but a actual, genuine dwarf who proceeded to pleasure himself there and then. So, be careful out there ladies!

I have 3 basic criteria: they should be witty, intelligent and not a minger. Simples. I keep this list front and centre in my brain before jumping into the fray:

1st Date – Anna (not real name)
I never know what to wear on dates so I keep it simple with no cologne or aftershave as it screams: douchebag, and besides I hate the stuff. We meet in a wine bar and I am so nervous my knees are practically knocking. She is very, very pretty and very smiley but… it is like interviewing someone for a job at Wickes. She is so boring that I cannot muster up any more conversation. I can talk to anyone, for ages, about anything, but she is a conversational North Face. I bail, getting a mate to pretend to be the babysitter. I really cannot question someone for two hours. Who am I, Jack Bauer?
1st Date – Fiona (not real name)
We meet in a bar and she turns out to be slim, good looking but not in a showy way and well dressed. Nice shoes – I like a woman with nice shoes. I was nervous but we chat easily about not much at all and conversation flows and she laughs at my humour. She is easy company. She says she likes me, a lot, and finds me very attractive and would like to go to my place and take me to bed. We have been chatting for 15 minutes. I am shocked and a little bit scared and (I admit) a little bit tempted. I try to explain my dilemma and make a bit of a fist of it. She says: ‘well, there is not point mucking about, is there? Maybe we’re not meant to be…’ She leaves. 30 minutes have elapsed. I go home and watch The Walking Dead and each nachos.
1st Date – Claire (not real name)
I have learnt from my mistake and arrange to meet for coffee, then I can bail early if it’s bad or arrange to meet for a drink later if it’s good. We got along marvellously on Whatsapp but she has omitted to inform me that the pictures she used were of her former, married self before she comfort-ate herself out of her post-divorce depression. I honestly don’t give a shit if someone is carrying a few kilos, but I do care about the deception. I am a bit guarded but we get along really well – we do kiss at the end – mainly because she is attractive and secondly I haven’t kissed another woman in nearly 11 years, so any port in a storm. Sounds callous, and it probably is, but I wanted to see what it was like, and it was nice, but I wonder if it could have been nice with anyone? I need to think if a 2nd date might be worthwhile as I like her. But the deception niggles at the back of my mind, so I’ll hold off arranging it until I have met my 4th 1st date.
1st Date – Megan (not real name)
We meet for coffee again. She seems nice, open and attractive. We chat in a relaxed way for a bit. We even flirt a little – it’s very subtle but it’s there. I am starting to think I might be onto a 2nd datee but, because my OKC login name has cat in it somewhere, she asks a question, out of the blue:
‘So, do you love cats then?’
‘Well…they’re okay I guess,’ I said.
‘You do have a cat?’
‘Yeah, but I only got it because of the kids,’ I replied.
‘So, you don’t love cats?’
‘They’re okay…I guess.’
‘I think we’re done here,’ she says and leaves.
So, this is all going down while I chat with the chat happy women and slow repliers (it’s instant messaging, so it’s just game playing I think…). I organise a date with one of the slow repliers and one of the chat happy’s and a 2nd date with Claire…because we got along. Plus a new woman matched with me and we quickly organise a date.
1st Date – Donna (not real name)
One of the chat happy people. We got along famously on Whatsapp and she seemed very witty and intelligent. She is that in real life too and we have a great evening that is funny and easy going and I could see us having a lot of fun together. We kiss at the end, but nothing heavy as I have to catch a train. I kissed her mainly to kiss another girl. I think about her on the train home and realise that although I like her I don’t find her attractive, not enough, which sounds a bit shit, because I kissed her, but I made a promise to myself to be as honest as I could without hurting anyone’s feelings. I go radio silent for a couple of days and tell her that it was fun, but I could only ever see us being friends. She takes it quite badly and says I have been playing games with her. Hmm, have I?
1st Date – Eliza (not real name)
Eliza is the youngest woman I have met (exactly 35) and is pretty and turns out to be an opera singer. It also soon emerges that she is quite possibly – maybe definitely – crackers. She flits from one subject to another and seems to be into everything from aromatherapy, heavy drinking, yoga, doom metal, tantric exploration and Pokemon. She is really touchy and is it quite off putting, She says she is a non-smoker but nips out of a cigarette halfway through. She wants to show me her record collection and sing to me at her place. I make my excuses and leave. I think she might eat me alive – literally as well as metaphorically.
1st Date – Clara (not real name)
One of the slow repliers. Organising a date with her is like trying to dock with the international space station – but we eventually meet for supper (her suggestion). She is pretty, intelligent and easy to talk to. We have a nice evening – there is no fireworks though so I have no idea where I stand with her as she is not very emotive. I don’t get any chemistry from her but think it’s early days and maybe she is like that. Which would not be easy as I prefer a bit of feedback from my partner. She is a possible 2nd date. But I am not feeling overwhelmed. We don’t kiss at the end: never a good sign.
2nd Date – Claire (not real name)
After some gentle pressure from Claire we meet again, this time in the evening. We are relaxed and flirty and have a nice time. We don’t drink much because she is driving – and I figure that getting drunk on a 2nd date is probably the worst idea EVER. She offers to drive me home which I accept – we kiss and it gets pretty intense. She suggests going to my place and I am no Tom Tom but I know where this is going…I put the brakes on and say that that might be too quick for me. She is cool about it. The thing is is that sleeping with someone is a big deal for me (I know it is not for many guys – I have only slept with 3 women, ever; and one of those was a mistake!) and I want it to be with someone who I really like. I was really, really tempted to sleep with her anyway, just because I could. But I think that is not enough of a reason even though I haven’t been laid for (shit!) nearly 3 years. I go radio silent for a couple of days and say that I want us to stay friends but nothing more. She takes it badly. I feel a bit shit. But better end it now than later, right? God I hate this.
I hold off arranging dates for a couple of weeks. The whole process has left me feeling a bit shit about myself and I wonder if I have behaved like a bit of a arsehole. I cannot decide if I have or not but resolve that I am going to hold off meeting anyone for a while. Clara wants to meet again but I don’t know why. I stall her a bit and in the end I don’t need to as arranging a 2nd date with her is as complicated as string theory.
I get a random message from a girl called Selina, who I messaged ages ago but got no reply. She has been travelling for work and has been working her way round to my message. She says she is finding Tinder men a bit one dimensional and she has been on a bunch of first dates but they all turned out to be duds. We chat openly and honestly about the process. We don’t arrange a date.
Clara is pushing hard for a 2nd date but I keep saying I am busy. I am not in the mood for it and I don’t know what she wants. I go on a huge cycle (I have managed to lose 12kgs since my divorce – ha! Take that, ex wife!) and when I take a break it transpires, through some texts, that I am about a mile from Selina’s work. She suggests meeting for lunch. I haven’t shaved for a week, am in Lycra and have no money and helmet hair. I probably smell a bit. Against my better judgement I agree.
1st Date – Selina (not real name)
Selina turns out to be a very shy and softly spoken woman from Luxembourg. She is so pretty she is edging into beautiful and I actually quietly gasp when I see her. I am, for once in my life, a bit tongue tied. She has bought me a sandwich and a juice and we go to the park and chat. It is easy and relaxed, I make her laugh and she makes me laugh. She is completely out of my league but easy company. Besides, who doesn’t want to have lunch with a beautiful woman? We don’t arrange anything, but part with a kiss on the cheek. We spent an hour together but it felt like 10 minutes. She says the same.
Clara is still pushing for a 2nd date. I finally relent, just so I can try and halt any progress in person – seems the more dignified way to do it. Selina messages me and says she is going to see a band tonight in a bar and would I like to come? Its very relaxed but she will be with friends and work colleagues. I say that I am, unfortunately, busy but it would be a bit weird meeting her for a 2nd date with all of her friends and work mates there. She agrees, but says they are really nice people and it wouldn’t be awkward. Hmmm.
Clara cancels – what a surprise, saying she is tired. I wrestle with it but finally decide to go see this band. It’s going to be awkward, but ho-hum.
2nd Date – Selina (not real name)
Selina is terrible at social situations, it transpires, and is quiet and watchful. I am, however, in my element and keep her friends and colleagues entertained and make them laugh. Selina is never far from me and she misses nothing and we manage to speak – tops! – 1/2 an hour all night. I have to leave to drive home, she walks me to my car. We kiss…a lot.
Anyway, long story short I am now dating Selina. She is utterly awesome and turns out to have a wicked sense of humour and I am – rather like a supertanker hitting a beach – slowly and inexorably falling in love with her. So, sometimes it does work out online – but boy, it is sometimes trying and reveals more about oneself than I thought.




  1. 29 May, 2014 / 2:48 pm

    Very funny and interesting post! I’m struggling with online dating, mostly because of my location, but this has given me a bit of a push to try harder! I hope things continue to work out for him!

    • Jo Middleton
      30 May, 2014 / 11:33 am

      Thanks for reading! It was interesting wasn’t it? I found it very reassuring!

    • Casparthecat
      30 May, 2014 / 12:40 pm

      Don’t give up Mrs Teapot. A wise woman once said: ‘don’t let geography get in the way of good friendship or matters of the heart.’

  2. Simon Howes
    29 May, 2014 / 7:19 pm

    To the mystery writer… Thank you. Thank you for showing not all men are douches. I wish you well with your relationship!

    • Jo Middleton
      30 May, 2014 / 11:34 am

      It was great wasn’t it Simon? Lovely to get in glimpse inside a man’s head!

  3. Sarah
    30 May, 2014 / 11:22 am

    You’re 42 and you’ve only slept with 3 women IN YOUR WHOLE LIFE?

    That’s hilarious! Loser badge in the post to you.

    • Jo Middleton
      30 May, 2014 / 11:32 am

      How on earth does that make someone a loser Sarah if they choose to only sleep with people they really care about??

    • Casparthecat
      30 May, 2014 / 12:33 pm

      Hi, I am ‘guy’ who wrote this. I have an old friend who has been married to his childhood sweetheart all his life and they are still very much in love, have 4 kids and (from what he tells me) a voracious sex life – she is the only woman he has slept with, is he a loser too?

      Also, If I had known the secret to happiness was how many notches I could put on my bedposts then I should have slept with a different woman every week. All this ‘finding a soulmate’ and ‘falling in love’ business is way over-rated…

    • Casparthecat
      30 May, 2014 / 12:35 pm

      Oh, and: 4

      • Simon Howes
        30 May, 2014 / 1:13 pm

        I’m three for 31years with hopefully zero chance of that first number changing.

  4. Stevie
    30 May, 2014 / 6:17 pm

    I’m convinced this is written by a lady but I liked it lots.

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