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Dating Your Ex's Best Friend (7 Crucial Things)

by Sonya Schwartz

Whether you’re interested in dating your ex’s best friend or you’re already romantically involved with them, you’ll most likely be feeling that the situation you’re in is extremely complicated. However, the situation isn’t actually as difficult as you might think it is, and as long as you follow a few guidelines!

In this article, we’re going to be sharing the 7 most important things that you need to do if you’re planning on having a relationship with your ex’s best friend, or if you’re already involved with them.

1. Make Sure You’re Over Your Ex And Not Trying To Get Their Attention

The very first thing you need to do is make sure that you are completely over your ex-boyfriend. If you have just come out of the relationship with your ex, or you still have feelings for them, you might be dating their best friend out of spite.

As long as you’re certain that you want to date this person because of who they are, and not because you want to anger your ex or get back at them for the breakup, then you’re all good to move forward. 

However, if there’s even a small part of you that’s trying to date this person to get back at your ex, do not date this person - it’s not fair on them, or you and it’s just going to cause pain to people that don’t need to feel it.

2. Be Sure That You’re Serious About This New Relationship

be sure that you're serious about this new relationship

Do you want to have a one night fling with this guy or are you genuinely interested in having a future with him? If you’re going to invest a lot of time into figuring this situation out, risk upsetting your ex and potentially break up your ex and his best friend’s relationship, you need to make sure that you’re committed to having a relationship with this person, to make sure it’s all worth it.

3. Talk To Your Ex About Dating His Best Friend

Once you’re certain that you’re in it for the long haul with this guy and you’re not doing anything to get back at your ex, it’s vital that you actually speak to your ex and explain the situation to him. If possible, it’s a good idea to speak to your ex before actually dating their good friend, but if you’re already romantically involved, it’s respectful to let your ex know as soon as possible.

You should speak to your ex face to face to avoid any misinterpretation, and once again, as a sign of respect. It’s completely up to you whether you speak to your ex with his friend, or by yourself. 

You have to expect that your ex might be angry or upset, so try to be understanding and compassionate. After all, think about how you would feel if your best friend started dating your ex.

4. Create Distance

Regardless of how your ex reacts to the news of you and his best friend dating, it’s a good idea to create some distance between all of you, at least for a while. You don’t want to flaunt this new relationship in front of your ex, so avoid spending time within the friend group, and stay out of the way when your ex and his best friend spend time together. 

This is a useful and kind thing to do, at least until your ex is OK with you dating his best friend, and everything has settled.

5. Avoid Comparing Your New Partner To Your Ex

Although it’s natural for you to compare romantic partners from time to time, you should try your best not to compare your new partner and your ex. Even if these kinds of comparison thoughts pop into your head, do not vocally compare your ex with your new partner as it’ll make them feel uncomfortable, and it’ll cause tension between you both - this will obviously be amplified because this guy is the best friend of your ex.

6. Don’t Talk About Your Ex With Your New Partner

don't talk about your ex with your new partner

Setting boundaries with your new partner and your ex is a great idea, and one of the most important boundaries that you should set is to not speak about your ex or the times that you were dating your ex, with your new partner. You should never discuss previous relationships with new partners anyway, but particularly not when you’re dating the best friend of your ex!

Your new partner doesn’t want to know about how it was to date your ex-boyfriend, especially because they’re best friends and they saw you in that relationship. You may want to set a rule that you completely pass on the topic of your ex, apart from when absolutely necessary.

7. Move Forward, Being Mindful Of Your Ex

People have a right to fall in love with whoever they fall in love with, so move forward with this person and be happy - you do deserve it! 

Just make sure that as you move forward with this person, keep in mind that they are the best friend of your ex, so don’t go rubbing the relationship into the face of an ex, or act in a way that would hurt your ex or damage the friend group that both your new partner and your ex are in.


Is it OK to date your ex's best friend?

Although most people think that it’s unacceptable to date an ex’s best friend, you fall for who you fall for - sometimes things just happen! It’s OK to date the best friend of your ex, as long as you follow some basic rules that are set out in this article. 

As long as you’re certain that you’re over your ex, serious about the new relationship with his friend, and mindful about not upsetting your ex, things should be fine.

What should I do if my friend is dating my ex?

If your friend is dating your ex, it’s really important that you all practice clear communication with each other. 

You should try not to be angry with your friend or your ex, but also allow yourself to feel your emotions (they’re valid), set boundaries with them, tell them how they can respect you, and attempt to be happy for them. At the end of the day, if they want to start dating your ex, there’s not much you can do.

Is it OK to date your ex's brother?

Dating the sibling of your ex might be incredibly difficult and there will undoubtedly be a mixture of emotions that you need to work through with both your ex and their sibling. However, if you’re truly over your ex and you’re actually serious about a future with their sibling, go for it. 

Although this article is about dating the best friend of your ex, you can follow the advice and it’ll still work, even if you’re in this situation.

Is it OK to talk to an ex while in a relationship?

If you’re in a relationship and you’re speaking to your ex, it is acceptable, as long as you don’t have feelings for your ex anymore, your partner is OK with it and the conversation you’re having is completely platonic. However, if you’re in a new relationship, unless you’re still really good friends with your ex, there’s no real reason for you to be speaking to them anymore.

How do you know if your ex's friend likes you?

If you think that your ex’s friend might like you, look for these signs! They will be displaying signs of affection towards you, trying to hang out with you alone more often, speak to you more regularly, get jealous when you speak about your ex, and show body language signs that they’re attracted to you. 

You can check out the article, How To Tell If Someone Likes You to see what other signs you should be looking out for.


If you’re interested in dating your ex’s best friend, or you're already dating them, this article will help you to navigate the situation smoothly. Just be prepared, this isn't an easy thing to be involved in, but as long as you’re certain that dating the friend of your ex is what you want, then go for it.

Did you like this article and find it useful? Let us know in the comments and feel free to share with any people you feel need to read this.

You may also be interested in: 3 Easy Ways to Find Out If He's Cheating On You

Sonya Schwartz
A hopeless romantic that struggled for many years to find her Mr "Right" and made all the mistakes you could think of while dating. Known for always choosing the wrong guys or messing up relationships, Sonya was finally able to change her approach and mindset when it came to dating which helped her eventually find the man of her dreams and become happily married. You can read more about me here...

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