Tuesday 12 October 2021

Should a man date his mate’s ex-girlfriend?


Strategize the comic.  Humour the strategist.”


Reader rolexhandyman raises a question that hasn’t previously been explored in detail on this blog:

Hi Vinay
What is your take on dating a woman that had a sexual relationship with a close male friend. Would you ever do it? Is there any red flags?

My response:


A man’s essential function in life is to desire a woman who he is uncontrollably sexually aroused by.  A woman’s ultimate motivation is to be desired by men, and to feed off the internal feeling of this ego boost over and above the projected feelings she holds onto him.  Exceptions exist, but on a wholesale basis this is the course of events.

I’m sure any man with even limited experience with women has been romantically involved with at least one woman who, at any given opportunity or even without a conversational link, mentions an ex-boyfriend.  Worse still, you may have been entangled with an ex-girlfriend who blabs on about numerous exes.  It isn’t a very nice feeling, is it?

On the other hand, whilst women will also say that they don’t like the inner feeling when their current boyfriend talks about his ex-girlfriend/s, there is a discrete difference between the two equivalent gender dynamics.  Whilst a man is neither impressed nor further attracted (and in fact is less attracted) to his girlfriend mentioning her ex, a woman, although her ego is squashed in the immediate emotion, is actually more attracted to a man when thinking of a woman he was once nailing (providing his ex is not significantly less physically attractive than her). 

With all that said, it is no surprise when you hear about, and see with your own two eyes, women attempting to poach another woman’s man.  Sometimes this can even be a man who is a female “friend” of hers.  However, when it is the inverse scenario – one woman acting as the triangle with two other men – the matter is a little more complex to understand and explain.

A first-hand example

A good time ago now, I sat in the health centre steam room when a man I knew walked in sporting a bruised and cut eye that would not have been inferior to the aftermath scars seen in last Saturday’s Fury/Wilder III fight.  I knew him on a conversational basis, not only through seeing him in the gym, but also as we had recently played on opposite sides of an indoor soccer match.  He had an excellent body, an ideal height of 6ft 1”, although facially average (even before the black eye!).

I naturally asked him what had happened.  He paused a little and sighed, but then went on to tell me that his best mate had clocked him one.  I then asked whether it was just a drunken fight on a night out.  He responded by confessing that he had slept with said best mate’s girlfriend.  My first verbal response was to the words of who needs enemies when you have friends like him - with the dig being at him doing the dirty.

I don’t know what either the woman or other man in the dynamic look like, which is a shame as I’m a firm believer a person’s physical attractiveness level lays the foundation to many explanations of bewildering, and sometimes logical, occurrences in the world regarding emotional decision making.  My guess, with no proof, is his mate would be below him in overall physical attractiveness by a pronounced degree, and she was somewhere between cute to lower end hot.

I did press him a little to the ins and outs and the hows and whys, but I could tell his shame didn’t want to elaborate much more.  He was probably no older than twenty-two back then, and I could tell there was still that immature mentality of notch count precedence over male friendship loyalty, however even at that age I’d like to think that a couple of the other men in that male group disowned him for a period of time.  If people have no fear to the consequences, they will continue to commit the same crime.  Whoever said the phrase of “bros over hoes” is universal?

What is my take?

Rolexhandyman asks for my take on the consideration of dating a woman who had a sexual relationship with a close male friend.  I think you already know my answer, but it is a straight, direct, and unequivocal no way.  This stance is reinforced even further if it is a man’s brother.  I’ll expand on this…

·       First, recall what I documented at the top about the irritable feeling you have when your girlfriend mentions ex-boyfriends.  If you choose to date a woman who was once convoluted with your close friend, you are effectively giving your mind a free passport, with no prior proverbial travel checks, to feel this negativity inside such is the high likelihood that you will collide with him in frequent passing or she simply keeps mentioning him by accident or deliberation.  A slight mitigation would be if the two of you moved to another location far away from his residence. 

·       Second, and connected to the first point, is the topic of sex.  No honest man really likes the thought of another man previously nailing his current girlfriend, but in today’s realistic world you have to accept that most woman you meet over the age of eighteen (and often younger) will have experienced at least a handful of other penises inside her.  If you have knowledge of who the other men are, and compounded once more if that other man is a close friend of yours, I expect this bitter feeling to be five-fold greater.

·       Third, relationships with women are complex, demanding and infuriating enough at the best of times.  Why make this any harder in dating a woman who was once sexually involved with your close friend.

·       Fourth, in spite of his possible blessings, and even in light of possible early banter that the two of you have nailed the same girl, there is a greater chance that your friendship bond with your mate will never be as strong as it was prior to all this.  Good male friends are far, far harder to find than a woman you want to have sex with.

·       Fifth, whilst belonging to a minority in the whole scheme of things within the female population, there are plenty of cute and hot women out there.  Some of these even have a half-decent personality, and some still are potential girlfriend material (granted, this percentage is shrinking year on year).  With this in mind, there are numerous other women who could take the place of a close friend’s ex-girlfriend 

Why would the man and woman do this?

Take another look at the Q-tip above.  The man in the anecdote would have been led by his penis.  I doubt it was her unbelievable likeability that made him sleep with his best mate’s girlfriend.  Simply put, it was nothing more than his sexual urge, possibly on a drunk night, which made him do such a thing.

Conversely, the girlfriend in this triangle attained far different emotions.  Sure, if, as suspected, her boyfriend was less physically attractive than the man she cheated with, then there would be a biomechanical function, not dissimilar to how men process, which made her adulterate.  Nevertheless, these following reasons are what would have motivated her beyond her sexual attraction.  This can be taken as a general concept, and not isolated to the three people within the anecdote:

1)    The need for further attention.  It wouldn’t surprise me if she was the perennial girl who spends more social time going out with her boyfriend and his mates rather than her own female friends.  It wouldn’t surprise me further still if she was the type of woman who says she gets on better with men than women.  In easy interpretation language, a woman of this kind is an attention seeker who can’t bear the thought of any other women (especially other hotter women) having more spotlight on them than her.

2)    The need to feel important.  Dating a lesser looking man in gender comparative terms can give a woman a short to medium ego thrill feel boost, however this feel-good factor is perishable.  Over time, she will seek other sources to feed her importance/popularity needs.  Cheating with another man, even a man who is a good friend of her boyfriend, will alleviate this hunger in the immediate term at least.

3)    Associated with 2), the need for people to talk/gossip about her.  Magnified by the social media world we live in, the female craving of being talked about or attaining comments/likes on her social media page is at an all time high.  There is no sign of this slowing down.  A woman sleeping with her boyfriend’s mate will know exactly what she’s doing before an ounce of alcohol is consumed, and her motives of this having people talk about her will be a factor.

4)    The need for partner validation.  Many women don’t enjoy being single for long.  Most women of this nature will already have their next boyfriend lined up prior to the current relationship ending.  If it means having a boyfriend, or more important to her being of girlfriend status, she will have no care in it being a friend of her ex.

5)    Dating only within her social network.  Exacerbated by the last eighteen months of COVID-19 (and the social mixing restrictions that went hand in hand), women have seemingly over recent years been inclined to seek boyfriends who are already within their social circles.  A lot to do with this is a by-product of 1), 2) and 3) as given above.  In simple terms, dating a man who her existing social circles know about will bring more highlight onto her life.

Are there any red flags?

The red flags, from the potential girlfriend (or lack of girlfriend) material perspective, should be self-explanatory as spelt out in 1 to 5 above.  Fundamentally, you are running the risk of being tangled with a woman who holds an attention-seeking mindset and who is far more interested in feeling good about herself and popular in the eyes of others than she is barely, if at all, bothered about who she impacts negatively along the way.

As a best analogy that comes to mind, a woman of this type will happily drive recklessly if it means making her destination on time, in not even looking in her mirrors to who she has killed along the way.  And if one day the police did come knocking on her door, she would have little remorse, hiding behind weak excuses and justifications to why she acted in such manner.

A final thought

There are so many giveaways, even in the early days when women are on their best behaviour, to whether a woman you become romantically involved with will be good girlfriend/long term material.  It begs belief to why so few men pick up on this, or more likely, why they are petrified to accept this reality.

And I’m not going to be a total hypocrite here.  Whilst I have never been sexually involved with a mate’s ex-girlfriend, there was one time when I was eighteen that I pursued one of my best friend’s exes.  He gave me his blessing, although if I’m honest part of my incentive was because he hunted her after he knew I was interested.  I guess it was innocent naivety on my part, to be kind.

I have also been involved with married women.  Whilst this may come across as a contradiction to what I have documented in the past – that it is far better to be with a woman who is single than a woman who has another man in her life, all else equal – by majority it was more a sense they were married/engaged than knowing with confirmation.  Also, knowing that most women perceive me as poor long term male partner suitability, deep down I knew they were only using me for their physical requirements.  The end results (hence them going AWOL shortly after), more often than not, proved my instincts to be correct.

So, my final words to the ultimate question – dating a woman that had a sexual relationship with a close friend - would be to not even consider it for a single minute.  There is truly little to gain, in relation to what you have to lose or will detrimentally go through.

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