Is It Wrong To Date Your Ex's Best Friend? No, BUT...

Adhideb Ghosh
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Entering the stage of dating drama is quite an enchanting world of reality. As much as we want some scenes to be a “play”, it turns out to be real-life scenarios! Dating your ex’s best friend is one of such scenes that hold every possible emotional and mental push and pull you can think of within itself. 

Dating your ex’s best friend can be a funny irony to experience or it can be a brutal situation tearing apart otherwise beautiful relationships. Due to such immense complications, when such situations arrive, people tend to get utterly confused and suffer from various dilemmas that eventually affect their relationships. 

So, if you ask me if it’s wrong to date your ex’s best friend, I would say, NO! it is not wrong to date your ex’s best friend. However, if you are in love and considering walking towards this person, rest assured that it will test the dynamics of their friendship and emotions with you in which everyone is involved. 

Look, I agree that friendship is indeed a bonding that needs to be valued. But when things come between your love and someone else’s friendship, there’s no wrong to put your steps forward and let the person on the other side take his/her decision. 

Giving you a better approach to this thoughtful situation, here is an article I am sharing in order to make things lighter for my beautiful readers. Hopefully, this is gonna help you to clear the smoke of confusion and dilemma and take things forward in a healthy way.

Ask Yourself WHY?

Identifying the reasons and rationale behind anything is the first step of solving any problem or confusion no matter how complicated it is. If you’re aware of your own intention behind what you’re doing, the path ahead is gonna be crystal clear hence easier for you.

So, your ‘WHY’ behind any and every action in life is the only thing that matters. In this context what we’re discussing, the consequence of a relationship you are approaching with your ex’s best friend will reap the fruits of your truest intentions only.

So, before moving forward to understand the reasons and rules of dating this best friend of an ex-partner, I want my readers to ask themselves WHY.

WHY do you want to date this person? Is it a move of a revengeful plot for the past breakup? Is this only to spy or for staying close around your ex?  Is it just a hookup story? OR, Is this connection genuinely meaningful where you both are serious

Breakups are indeed messy affairs and are traumatizing to thousands of people. However, if you are forwarding with a revengeful mindset, I suggest your approach is only going to mess things up further and get you nowhere. 

But, if you are intuitive about a genuine connection with your ex-partner’s best friend, you should take a chance, no matter how difficult things may look in the beginning. 

So when you’re in doubt or suffering from an initial dilemma, question yourself first. Then have the courage to listen to the voice that comes from within your soul. Be sure of the reasons why you want to go for your ex’s best friend. The rest will follow! 

When Can You Date Your Ex’s Best Friend?

If you just got a green signal from yourself to proceed with this connection of dating your ex’s best friend, it is now time for a thorough think-up! Always remember that sometimes our decisions play no role to be right or wrong. It’s the TIME who decides everything and makes things work. So, if you choose the wrong time all your efforts may go into the vein no matter how much potential it had. But you pick the right time, you may not have to put that much effort to make things work in your favor. So, learn to choose the right time and see your date blooming into a beautiful relationship.

But always remember that your current situation is far different from any regular dating story. Thus, it will require more of your efforts, understanding, and acceptance to make this date work at the right time. 

Mentally Prepared To Start Fresh

Entering the dating stage after a breakup can be quite hectic mentally and emotionally. But, when it is with your ex’s bestie, it will only require more of your mental preparation. Being a close observer, he/she will know most of your past details both good and bad.

Thus, before hitting the cafe with your new date, make sure you are pursuing him/her with a fresh mindset free from all your past wounds and breakup trauma. After all, dating his/her best friend’s ex is possibly awkward to him/her too. So, it’s your duty to make things comfortable between you two. 

There Is No Lingering Energy Of Your Ex-partner

Any woman/man must not date their ex’s best friend out of a revengeful mindset. That is a big NO-NO! You can only date him/her if you are emotionally free from all the lingering energies of this past connection with your ex. Connection with his/her best friend just to make your ex-boyfriend/girlfriend jealous, insecure, and awkward, or to stay around in close vicinity should never be your goal. 

Understand that it will not help you trail out of past trauma or fix everything with your ex. Rather, it will simply create more problems and potentially ruin their healthy friendship too. So, date his/her best friend only if you are completely over him/her and have genuine feelings for your ex’s best friend. 

You Are Emotionally Healed

Oftentimes we move on after a breakup. But, many times emotional trauma, stuck in our subconscious, remains otherwise unnoticed and stops us from moving forward in a healthier relationship. I have felt it myself and no matter how hard I tried building a new connection with another woman, I ended up emotionally tired and alone. 

So be it your ex’s best friend or any other man/woman, before you start dating again make sure to heal yourself emotionally off all your past trauma baggage. Seek help from a professional healer, therapist, or life coach if you need it. At this time, people tend to choose those persons for dates who are very close to your ex-partner, and thus your emotional traumas can only mess things up and ruin relationships further. So, before you proceed with anything, evaluate your inner being. Work on all your emotions and then put steps forward. 

It’s Not A Mere Infatuation

Sometimes, due to some toxic past experience with our ex, we tend to think how sweet it could be if it was his/her best friend instead of him/her! This state is called a mere phase of infatuation when our mind starts comparing our ex with their closest ally. Make sure that you’re not going within such a phase. Again, self-evaluation plays a critical role in this context. 

Set Things Up With Your Ex And His/Her Best Friend

Saying this, I want to highlight that it is not only about you and your ex-partner. This situation also involves your date and his/her best friend. In order to keep things healthy between all three of you mutually, I would suggest a few more ways to make things work out a little better.

Communicate Clearly With Your Ex

There is nothing like a soulful open conversation to clear the air of any possible confusion or misunderstandings. As you are planning to date your ex-partner’s bestie, an open conversation about what is going on becomes utterly important.

It is not that you owe an explanation to anyone, but your date is a dear friend to your ex. Dating you should not lead to losing his/her friendship. 

This is a very fragile and emotional situation for all three involved and hence it has huge potential to make things messy. Having a healthy one-to-one conversation if possible will be proven a great remedy for all possible mess. 

Clear All Misunderstandings From The Past

If you and your ex-partner still have any misunderstandings and fights that are to be cleared up, go ahead and do whatever is needed. Breakups can be messy and painful or sometimes mutual splits. Whatever it is in your case, make everything clear before initiating a date or entering into a relationship with your ex’s bestie. This will help you to start afresh and avoid any sort of future misunderstanding and mess-ups.  

Be Open To Understanding And Accept Any Clash

Your ex-partner may not appreciate the idea of dating his/her bestie, even after having open and clear communication with him/her. Well, honestly there is not much you can do here. Simply, be open enough to understand his/her mindset regarding this situation and put your best efforts to not act from momentary triggers. 

Be wise enough to clear any misunderstandings and not let the past ruin your present. If you have genuine and mutual feelings with your ex’s best friend, be courageous enough to make a healthy choice for yourself. Fingers crossed for the rest to fall into place!

Build Healthy Boundaries

When it comes to building healthy boundaries, people always tend to step back and allow others to walk over their personal space. I have done this myself and seen fellow men and women doing the same. 

Learning to build healthy boundaries for ourselves is highly important, especially while dating an ex’s bestie. Be vocal about your relationship boundaries and let your date know about the same. Joking about your past relationship with his/her best friend, or discussing internal affairs of your relationship with his/her friends is not something to be encouraged. Remember, this is only to keep things healthier mutually. 

Allow Space

No matter how healthy things are in-between you, your ex-partner, and your current partner, respecting one another’s privacy and space is very essential. Understand that your current date is THE best friend with your ex-partner. Things may be awkward and may feel uneasy, but they will require a bro-zone to be in without your interference. 

Things To Keep In Mind While Dating Your Ex’s Best Friend

I hope, by now you have a crystal clear idea of exactly when you can consider dating your ex-partner’s best friend...

However, as you are dating this new person already, here are a few rules especially for this person as he/she is already from your past. I want my readers to keep in mind that this new connection is NEW, hence no matter how many memories it carries from the past, they should never interfere in the future. 

Do Not Keep Talking About Your Ex

While in a relationship with your ex’s best friend, do not only keep talking about him/her every now and then. This often pinning up can make your partner insecure and plant seeds of doubt and misunderstandings. This has the potential to not only disbalance your new fresh start with this relationship, but also mess up their friendship. It is thus important to be careful about what you say and how you say it. 

Do Not Date Only To Hook-up

If you’re feeling lonely after breaking up with your ex and it’s been quite some time that your body and hormones have not felt the rush, get a new adventure maybe. But, getting your ex’s best friend is not a good idea at all. Do not hit on your ex’s bestie for only hooking up. You are only messing things up for yourself and that is not the right way to stride out of a past breakup. 

Do Not Rush

I understand that you know this person and maybe for a long time now. You have spent time before in friends’ groups and walked in front of them holding your ex’s hand. You share a strange comfort zone with this person and hence you think, this time that comfort zone will work as well. This is the first mistake many people make while dating their ex’s best friend. 

However, it is never wise to rush a relationship, no matter how well you know the person. Relationships have different dynamics than friendships and known acquaintances. Take your time to know the person better and take things slow. 

Do Not Compare

Never make the mistake of comparing your current date with your ex-partner. In your case, as he/she is your ex’s best friend, a comparison is the worst thing you can do. Every person is unique on their own. Whether you feel for the person or not, be ready to accept them with all of their pros and cons. Comparing your current partner with your ex, who also happens to be their best friend will only create more insecurities and problems in your otherwise blooming relationship. 

I hope this has answered, “Is it right to date your ex’s best friend or not?”. Love is love! And if you are in love and feel a genuine connection with this person, there is no right or wrong here. Follow your heart’s calling and hope for the rest to fall in place with time. Simply remember to not do anything for all the wrong reasons. Dating your ex’s best friend is that simple! 🙂

Related Queries:

Here are some frequently asked questions people generally tend to ask while dating their ex’s best friends. Hope this will help you too. 

Should I hide anything specific about my past while dating my ex’s best friend?

No, you shouldn’t. Don’t see your ex’s best friend as some alien. Treat him/her as just another simple person you are dating. First, make it clear that the connection between you two is completely new and it has nothing to do with the past incidents. Then slowly and gradually tell him/her everything whatever you feel is necessary. But maintaining some healthy secrets is good for all relationships no matter whom you’re with.

How long should I wait before having sex with my ex’s best friend?

It totally depends on person to person. If you feel comfortable and sure that he/she won’t judge you with the physical intimacy, you can go for it. But it’s advisable not to rush while being in such complicated relationships and being with someone for just hooking up is a big NO-NO. 

Does a relationship with an ex’s best friend have any future?

Yes, why not! Again, I wanna say that if you two can make things work properly, it can last forever. If everything goes right, after a certain point of time, you’ll start forgetting that he/she was your ex’s best friend. Who can say, he/she is the person who is the perfect match for you. 

How should I avoid talking about my Ex?

Don’t force into anything. If any topic related to your ex is coming up during a conversation, don’t avoid talking about it. Rather, deal with it sportingly. Believe me, it’ll help to strengthen your relationship. But obviously, you shouldn’t initiate any conversation about your ex and avoid talking about your past all the time. If your partner is doing so, a clear conversation is the ultimate way out. 


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