Should I Date My Mates Ex?

March 25, 2014

This is not a common situation that arises but it’s almost like a taboo subject. Dating your mate’s ex is like facing those sticky situations we would never wish to get into.

If you’re reading this, I believe that this topic has aroused your curiosity on how to handle such awkward dilemmas. Here, we will share with you some discussions and debates in dating a mate’s ex. Evaluate them in a clear mind before deciding on how to proceed hence forth. It is certainly more complicated than meeting a London escort.


First things first, there’s no clear cut right or wrong in this. When it comes to affairs of the heart, there’s no control over who you should or should not fall for.
The decision to act is dependent on a lot of scenarios and there are tons of questions you should ask yourself before moving on. There’s also different ways to approach it dependent on if you’re a male or female.

So let’s move on to take a look at it in the various aspects, and answers you have to seek.


Jealously and pettiness is common among women. When it comes to dating a friend’s ex, there can be misunderstanding situations where by you are thought to have already harboured feelings when they were together. This easily creates disputes and strains in the relationship.

Whether it ended off amicably or in an eventual nasty breakup, it’s likely that they never really got over their ex.


I am not saying that there’s no jealously amongst men, but that pettiness is definitely much lesser in general.

Do keep in mind that this situation could fragile and take a hit at your mate’s ego. The fact that things didn’t work out between him and the ex, and that she’s getting together with you could make him feel that he was inadequate in some way or another.

Communication would probably be one of the best tools for this. You could find out a lot more about this ex from him and understand why they broke up, and perhaps understanding some of her qualities which may not be suited for you.

How close are you with your friend? Is he/she your best friend?

Your girl best pal could be the one who has been there for you through these years, providing you a shoulder when you were crying and getting drunk over a man. Same goes for your best mate who may have been through thick and thin with you these years, doubling up as your punching bag, favourite drinking mate and your best soccer buddy.

Would he/she be understanding enough to give you blessings to get together with her ex? If you do get together with her ex, is this friend someone you would be willing to forgo? If you’re not really that close to them, by all means go for it. If they meant the world to you, consider looking for someone else then.

How long were they together?

If it was just for a short term, it’s more likely that there were not deep attachments or intense emotions involved. This would give you a better chance to get them to accept the situation of getting together with an ex.

How long has this relationship been over?iStock_000010923491XSmall

Is he/she completely over the relationship already?

You of all people would probably know this better than anyone else, especially if it’s your best mate.

If you still hear them mentioning how special that past love is for her, you know it would probably be an ugly situation when they find out you wish to date the ex.

If this person was never ever mentioned again since breakup, perhaps your mate has already long forgotten that such an ex existed!

Has he/she already found someone new?

If your mate is already happily attached with someone new, you could try to sound them out on how they feel about it.

Having already met someone new and probably better and more suitable in their view, this past relationship could well been buried in the memories and you may even receive their blessings!

Are they still in contact with each other?

If they are still in contact with each other, are they now loving each other like family members, concerned for each other like friends or are they just waiting for an opportunity to get back together? You would know how you stand then.

couple in bed, man without cover, woman is sleeping, HQlypse

Who got dumped?

If your friend was the person being dumped, it is likely that they never forgiven that ex, nor got over it.

However, if the situation was reversed and the ex was the one being dumped, there’s almost no reason why you can’t go for it.

Bottom line

Ask yourself whether this person is worth losing a friend for. Is he or she even interested? There’s no point in advancing foolishly when the other party may not even know how you feel.

Communicate with your friend in a rational and calm manner and at the same time, be tactful of how you put things across.

Be honest in the things that you put across such as how you don’t wish to lose them and you respect the way they feel about such a situation. Test them out by creating scenarios of such things happening to your imaginary friend and see how they react. You would be able to get a gauge on their own reaction when facing similar situations.

As their mate, you would be able to know better whether they were giving you sincere and true blessings or if they were reacting in a surface manner, secretly fuming and wishing to exact revenge on you on the inside.

If you do eventually get together with the ex, don’t flaunt your love and flirt publicly. It may not be something easy for them to accept and give blessings to.

Do be sensitive about how your friend would feel and put yourself in their shoes.

Remember, friendship lasts a lifetime. Be careful before you threaten to ruin it.

Martin Ward
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