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Keeping it casual in toyboy and cougar relationships

Keeping It Casual

With all the literature surrounding dating, several questions often get overlooked or are only given uncomfortable lip service by the average Joe-public.


Is it okay to date multiple people at the same time?


If it is, how many should you date?


These questions often come to the fore of my mind when I’m single as I don’t know if I should feel liberated for dating multiple women at the same time, or feel really awful.  One thing I have learnt is that there are 2 types of singleton.  Which one you are can drastically define your approach to dating:


  1. The singleton who is looking for a relationship
  2. The singleton who is looking for casual sex


There is overlap.  For example you can start dating one person you think you like and would like to try monogamy with only to realise a few weeks later that “Actually, this isn’t the one for me.” and end up either ending it, or sleeping with someone else when you’re still technically dating the one you know isn’t right for you.


There is also confusion.  For example one person might think they’re in a relationship whilst the other feels it is just a casual affair they can conduct along with several others at the same time.


In both cases the issue is usually the same; lack of communication between both parties.  I remember going out with a woman called Alexa several years ago who after our 3rd date (and aided by wine) we ended up back at hers and spending most of the night not sleeping.  The next morning whilst we were chatting, I casually mentioned that I wasn’t currently seeing anyone else when she asked.  Here’s where the confusion started and where I should have been far clearer in my communication.  She took what I said to mean “Oh, John has just said he isn’t seeing anyone else currently, which means he obviously just wants to see me.  Fair enough.  I won’t see anyone else either whilst we’re going out.”


Captain Idiot here took my own statement to mean “I’m not currently seeing anyone else…it doesn’t mean I won’t if I meet someone else.”  As it turned out I met a woman called Cecilia a week later, and we ended up in bed together after one date.  I told her before I slept with her that I wasn’t looking for a girlfriend at the moment, and if she wasn’t okay with that then I understood.  To my surprise she was fine with it and thanked me for being so honest.  Of course that’s when I realised I should have said that same thing to Alexa. We live and learn.


I know Alexa assumed I wanted to just go out with her because I talked to her about it a year later when we met up for a drink and did what we should have done when we first slept together; talked properly.  I apologised and she did too.  We were very mature about it all.



So coming back to the original question; is it okay to date multiple people at the same time?


Yes.  I think it is.  The fact you’re reading this makes me certain that you probably have several people lined up for dates already.


But is it okay to sleep with multiple people at the same time?


Yes.  I think it is.  As long as you’re open, honest and – I can’t stress this last part enough – safe about it, then who is anyone to judge?


Despite the massive temptation not to let anyone you’re sleeping with know you’re sleeping with other people as well, I would always recommend talking to all the people you’re seeing about what you’re doing.  You don’t have to go into graphic detail – no one needs nor wants a blow by blow account of what you did last night!  However by just letting someone know that you’re not open to a monogamous relationship at the moment enables them (and you) to decide sooner rather than later whether or not you’re happy with just sex, or if you want something more.


For a guy there is this fear that a woman will not sleep with him if he tells her he’s seeing other women as well as her.


For a girl there is this fear that she’ll be considered easy or labelled a ‘slut’ if she sees other guys at the same time.


Both fears are understandable, however they do both man and woman a disservice to each other.  Why?  Simple really; both parties are making assumptions about the other without giving the other person the courtesy of talking to them openly and honestly about how they feel and what they want.


There is nothing more damaging to any relationship – casual or committed – then a failure to communicate.


So just be open and be honest with yourself and with your partner…or partners.


As to how many people should you date at the same time, I’m afraid only you can answer that question!

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