Here’s Why You Shouldn’t Sleep With Someone On The First Date

Remember when I kissed Miss X at the bus stop? Well here’s fast-forward to the bedroom (I did promise you some action, after all). Well, this girl has an awesome little body on her – everything is just right.

At uni she was even known as ‘Miss X With The Amazing Breasts‘, and they are. But now things started to spiral down the plughole in a bad way. At this point I must confess that we had a little history in this department. Years and years ago we did once find ourselves in a similar situation, in what she unkindly refers to as The Claphamgate Fiasco. Actually it was Wandsworth (so much nicer) but suffice to say that after too much wine the entire episode resembled a man trying to encourage a recalcitrant worm to climb through a keyhole for an hour or so. I now had performance demons to exorcise, but of course knowing this only made me more anxious and therefore doubled the pressure. There was no way this was going to be easy.

Now girls, here’s something that you should know: the first time with a new person is a total nightmare for us blokes for a number of reasons:

1.  If he likes you he’ll want to create a good impression

The first thing you need to consider is that if he likes you he’ll want to create a good impression, which in turn will make him nervous. This is not conducive to stiffness in the lower parts. If he’s not nervous then he probably isn’t planning on seeing you again. Perversely this means that he might do much better (because he simply doesn’t care what you think and thus the pressure is off) but you can draw your own conclusions as to how desirable that outcome is. This is why you should never sleep with someone on the first date. It is quite likely to be your last too. Sorry, but that’s just the way we are.

2. Alcohol

Next up is alcohol. This is a double-edged tool. You’ve probably both already had a bit by the time you get naked and this is a fine thing. It makes you look more attractive to him and it certainly helped him get invited in by you, so to speak. It also works wonders in taking the edge off his nervousness but of course he needs to strike a very fine balance between relaxing just enough and being, well, just too relaxed down there. This balance is a critical point and in my experience makes the difference between having a reasonable stab at it, so to speak, and Claphamgate.

Alcohol also helps us to last longer, and this is clearly a good thing too since the first time we sleep with you we are going to be wildly excited and things may be over quickly. Take this as a compliment but don’t expect us to be up to much. And don’t expect us to be up too much either. Once we have got the dreaded first time out of the way we will be much more comfortable and things will definitely improve for you. Your time will come but you almost certainly won’t come the first time, so if you like the guy (and you should if you are at this stage) then he deserves a second chance, or a even a fourth in my case.

3. Keep the foreplay to a minimum

Basically don’t play around for too long before you get down to it. All the time this is going on we are dreading the moment of truth, so keep the foreplay to a minimum. I’m afraid that will have to wait until later on in the relationship. If you can get it in, just do so immediately. This will mean that he can start to relax, having shown you that he is minimally capable after all and not a complete loser between the sheets. Every failure enhances the dreadful thought racing through his mind that you will never experience just how good he can be because you’re going to give up on this hopeless bloke who can’t even do the simplest thing in the history of humanity. And probably tell your friends about him too, to add insult to injury.

This might all sound a bit dramatic but it is a surprisingly common situation for us men, I think. Now obviously I’m assuming that you are a woman since you are reading a fashion blog, or you’re gay (in which case my bedroom tips will be of absolutely no use to you whatsoever) so you may well have experienced similar farces from a female perspective. If you haven’t already, I hope you now know why they happen and how you might be able to help us out. If you are lucky, Miss X might tell you one day about a guy that she went out with who suffered from such a terrible spiral of positive nervous feedback that they didn’t actually manage to have sex for several months. She’s a very patient girl, and that was my eventual salvation. By the way, if you are neither a woman nor gay, and might be thinking of sleeping with someone for the first time, then why not direct her to this blog in advance just in case?

Anyway, getting back to the point, I totally blew it. Utterly, miserably. Claphamgate all over again, only worse since this time was supposed to be my redemption and I had been waiting 10 years for the chance. Every time she softly told me not to worry was an agony of embarrassment and frustration.  Could this get any worse? Well yes, it turns out. When we woke up in the middle of the night I tried again and failed yet again. Three strikes. Was I out?

Well, dear reader, no doubt you like a happy ending. So here’s the good news – we eventually made guacamole. No, really. Lunchtime the next day, and I was trying in vain to remove the skin from a tomato (is that part really necessary?). ‘Look, X,’ I said. ‘This is ridiculous. I can totally do this. It might not be up to much the first time, but by now your expectations must be so low that I can’t possibly disappoint you. Let’s go and sort out the problem like grown-ups.’ After all, we’ve been friends for 20 years, so if you can’t feel comfortable with someone you know so well then what hope is there? No booze this time to help me ‘relax’. Just two old friends who it turns out really do like each other, and don’t want to stay just friends.

So I washed the avocado off my fingers, took her by the hand and pulled her into the bedroom, leaving a trail of discarded clothes in our wake.

Want to read Mr W first column? See here.


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