We are quite pleased at the amount of interest shown in the first Ask Jimmy post and he’s had a look at the questions readers left in the comments below. I’m leaving it entirely up to him which ones he answers. Till then, here’s his thoughts on a question I put to him a few weeks ago.
Question: How long should you be a player?
6 months ago I was in Central London with my old mate Xants, rolling around, helping Xants look for skirt, Xants telling me how to get rid of my beer belly, when at one point we saw an excitable young pup running sets on Oxford Street. At one point he got kicked out of set, with a smile on his face and his chin up, just as we were walking past and seeing us watching, he acknowledged us and we got into conversation. At some point he asked me if I did game and I said that I did a few years ago, but I am 40 now and….. He looked at me through narrowed eyes and sagely advised me, as he talked over the top of me, that ‘age is just a number’. He then ran off down the street, as God is my witness, a jaunty ‘I’m a pickup artist’ hat perked proudly atop his head.
He missed the point of my statement. Who at 20 would understand the world through the same lens as a 40 year old man just because they share a common pastime? So, leaning heavily on my cane and puffing my pipe, I strolled on, probably complaining to TK about arthritis or gout.
As I reported last year, I am indeed back in London, working hard, saving up and bouncing around with the lads at the weekend. My girl is with me most of the year and I am on the whole pretty settled and moved along from those amazing, free-wheeling pickup days. I am happy with it all. I don’t know if it is because of my transition in particular or just the fact that most of my mates are getting older too, but the longevity of one’s game career has been one of the dominant conversations in our friendship circle this last year.
How long should we be players? How long should we pace the streets for hot skirt? It’s a juicy topic and I generally have two return questions for people when they ask that. My first being, do you move on from game through ‘preference’ or ‘necessity’? Are you off the team because you retire just after your peak but still on a high, or because you don’t get picked anymore? That young pick-up legend I met on Oxford Street was looking at it no doubt through the necessity lens. He thought I was complaining that ‘I can’t day game because I am too old’ (necessity), whereas I was trying to say ‘at some point, you’ll be over all this’ (preference).
(NB: I’m only 40, everyone at work thought I was 27. While I joke about it, I’m hardly past it).
You surely want to eject at a point that you choose rather than a point that confronts you? This may leave you having to accept that you quit while you still have a fair bit of juice in the tank, but also while your market value is still high enough to make you a chooser in the market place. We’ve all seen the fading Hollywood star who mismanaged his finances, left having to ruin is reputation doing junk movies in his later years because he didn’t milk it and cash out in time.
My second question is, what do you want out of life? If you just want to chase hot young skirt into your 50s, you will absolutely be able to, if you know what you’re doing. It’s been done before and it will be done again long after we’re all gone. I see it all the time, but from, let’s say early 40s, onwards, every year you spend you begin to take on some tiny compromises. It’s like weight gaining on you in tiny increments. The big thing is, you can be 50 and date a 21 year old 9, but it is more than likely going to be a sport fuck. Marriage  and kids are likely off the table. If you are 50 and decide you want kids, you’re going to be attacking the market from a very challenging position. You’re not Mick Jagger and having game, as good as it is, is nowhere near as much value as having written songs like ‘Brown Sugar’, ‘Sympathy for the Devil’ or even ‘She’s a Rainbow’.
So if you don’t want kids or marriage you’re fine, you’ve got years. But don’t stop reading yet, remember you may change your mind, as I did, for reasons I state below. I can only ever speak for myself  and here are some the things I noticed about me as got older.
Waning Enthusiasm – The novelty for game will probably wear off (but not much 😉 lol). The thirst for new skirt and just getting laid in general will wear off. You’ll always look at girls tits on the tube in summer, but sexual adventure in general will just slip down the priorities list. Likely far from your top three, it will likely not even be in the top ten. Of course it’s supposed to because by your 40s you’re supposed to have a family of your own. I remember last year telling Nick that (assuming I was single) if we met two double hot, slightly drunk, naive 19 year-olds in extremely short skirts, who wanted to party with us until the early hours back at our hotel, I’d say ‘no’ if my team had an important game that I wanted to watch. He didn’t believe me, but it’s absolutely true. Watching a great game is far more interesting to me than yet another bang with yet another skirt.
Shrinking Market – In my late 30s I dated a hot 19 year old who is now 22 and she would have married me if I’d wanted (and she probably still would). But at some point your market is going to begin to shrink. At 35 you’re top of your game and you can have almost anyone. At 40, you’re starting to be a bit of a wild card, maybe even a bit of fun. At 50, I guarantee you’ll still be able to clack hot young women, but at that time a family is a big ask for her and not all top drawer skirt under the age of 30 will be willing to commit to a 50 year old. When my dad was in is 50s, after his wife died, he dated a few girls in their early 20s, but they were clearly all just flings. Some may have married him I guess, but it was thin end of the wedge (meaning he got a bit lucky and the girls would have been making serious sacrifices, such as no kids).
Mismatched preferences – The larger the gap between you and your skirt, the less you are likely to share in values, preferences and desires. When you’re both 20, you can live the same life of work, clubs, festivals, political ideas and holiday destinations. I’m 40 and I’ve seen my last nightclub, I hope. Now this isn’t a problem, but what happens at 50 when I’ve seen my last beach party or maybe even my last long haul flight? Things you don’t consider now will rear their heads then, such as at 40 you have to change your diet significantly if you want to stay fit. That means your girl probably does too. Now that in itself isn’t a problem, but straight away you need to find a girl who is willing to make more changes and sacrifices for you.
Sacrificing your bloodline – All the above considerations lead to a fairly clear likely outcome. Men have it better than their skirted counterparts (I am talking here about women, not the Scottish) when it comes to shelf life… to a point. We can crank it until our 40s until we start to worry, but we do have a shelf life. I think I got out at a decent age. I didn’t plan it, it just happened. My girlfriend is much younger than me, good looking, a good friend and good mother and wife material. All this offered to me at the same time as I just couldn’t be all that arsed anymore.
If you want the family and that whole next part of your life, and if you can see it coming, then in your late 30s be sure to realise that you want to cash your value as close to the top as you can, balanced against getting the highest value mother you can find for your children. Now I’d suggest choosing the mother your kids want, rather than the porn star you want, in the same way you put your spare coin into a pension pot rather than spunk it on a red Porsche. You’re doing your future self a solid favour. I’m not saying you should settle with a 6, just that it’s quite possible you banged hotter skirt in the past. I look down the road and see how much I love my son, and I want my son to be as happy as possible. If I’d give my actual life for him, then I can surely choose an 8 over a 9, or a 7 for an 8 for him. She’s gonna be a 6 by the time she’s 30 anyway. I wonder if some people fall into the trap of thinking ‘I’m a pick up artist with a blog so my final girl will be the one my whole game career is judged against’.
It might be hard to walk away for good from the freedom of the single life and the sexual variety. Yes I think it is, because it’s so final. You close a book and can never, ever go back, not with much hope of doing it successfully. I notice back in Burnley the lads I know who have families and kids now are all really happy. They’re at times a bit downtrodden, possibly it’s because, as I believe, they did it very early before they got their money sorted and they cashed out while their value was still low and before they’d had time to experience any real adventure. But they’re happy and they love their brats. I don’t think, once you have a child, that you worry too much what point your wife is or was, as long as she is a good wife and mother. Like I said, they all look shit at 30 anyway. They’ll drop a point easy the five years between 23 and 30 and then after that God knows how fast they’ll plummet. It’ll be like taking a new car off the forecourt. If you don’t choose someone with good character you’ll be telling your mates ‘yeah she’s a total pain in the arse but she was a 9 once!’
By the time you’re 50 you’re probably not going to care all that much about shagging, so you might as well get busy making a little lad to take on the football match. Finally, for those of you who want to be single forever, let me tell you a story from my life this last 12 months.
I met an old guy. 75 years old. I knew him through his wife (20 years his junior) and his daughter. I met him at a party. He was like my dad, handsome, charming and a deplorable Marxist, but I stupidly really liked him. He’d lived a grand life (probably on the tax payers’ dime) and we nibbled at each other about politics. I considered smashing his head in on the canapés but we said we’d go for a coffee sometime. No doubt he wanted to trick us into thinking political disagreements are just part of the ‘wonderful tapestry of life’ rather than a life and death struggle.
The funny thing was he confided in me at me at this party that he was very old. He told me straight three times ‘I’m not much longer for this world, James’. It was November when I met him and by February he’d died of pneumonia.
At his funeral there was a picture of him in his funeral magazine thingy. He looked good. He looked top of the world, in a nice suit, cool beard, smiling like the cat that got the cream. The point is, he looked a man in his prime. I asked his wife how old he was in the photo and she told me he was exactly 35.
My heart sank, a whole 5 years my junior.
I was regretful because I never went for that coffee with the old bastard and I listened intently to the service. The guy lived a marvellous life and he died at the age of 75 surrounded by his young wife and three kids. He’d done it right and he’d milked the world for everything it could give him. He’d won. I took it personally. We’re all going to die and it’s coming at us sooner than we think, so play the game as long as you want, but don’t let your opportunities pass you by. Who is going to carry you to the final resting place? Who is going to care when you go? You can die in a care home, or sort it by your own hand, or you can be surrounded by your family. I don’t believe in the myth of the lonely old man, single old men do just fine playing chess in the park with their mates or sitting in the pub watching the footy, but is it the first choice overall? What’s their final 6 years like? What is their final 6 months like?
Whatever you choose, you’re choosing it today with each decision you make and the last decade will come probably sooner than you think. Our time is finite. We’re not pick-up artists forever. Enjoy it while it lasts because what is freedom today could turn out to be a one way ticket.
 I am just using the word ‘marriage’ in this post as a reference to ‘long term pair bonding’ I’m not advocating a position on the legal stuff. It’s just easier to type ‘marriage’ then ‘long term pair bonding’, though to be honest, I’ve probably gone and typed ‘long term pair bonding’ more in this footnote than I would have done had I simply used it in the post in the first place. I’d have probably only typed it twice, and this footnote is already 85 words long and I haven’t even finished yet.
 I’m always keen to point out that I am not an expert on skirt or dating, I ‘m probably not even close, but I am the world’s leading expert on my life and my experiences and I can just tell you what happened to me. Take that information as you please, I hope it helps.