So, you’re interested in your ex-boyfriend’s best friend – talk about awkward. Dating your best friend’s ex or your ex’s best friend is a no-no in any rule book you will ever find. It’s in the bro code, it’s in The Rules and it is generally the source of so-called “drama”. But then again, there’s always the exception that proves the rule, so today we’re talking about how to date your ex-boyfriend’s best friend. A taboo, for most people? Maybe. But that doesn’t mean it can’t be done; just that you need some tact.

Of course, when you first realize that you are attracted or seriously interested in the best friend of your ex-boyfriend, you may feel slightly weird about it. It’s a serious dilemma, and most people experience feelings of shame or guilt, in this situation. Do you go after the guy, and risk pissing the ex-boyfriend off? Do you let him get away and then always wonder what could have been? It is quite a pickle. But let’s take things step by step, shall we?

1. First thing’s first – figure out just how interested you are in this man. Is he just a passing interest or do you seriously want to become his girlfriend, because there’s a difference, and one is worth the hassle and the other just isn’t. So before you start wondering how to date your ex-boyfriend’s best friend, first take the time to realize if you really want him or not. Once you’ve got it all figured out, you can proceed to step two.

2. Now that you know that you really want to do this, you need to realistically assess the situation. Think back – how did your relationship with your ex end? Was it on friendly terms or did you have an ugly breakup? Do you still talk to each other regularly or have you ceased all contact? This information is important, because it makes the difference between needing to tell him about your new-found interest in his best friend or not.

 

3. Another thing – how serious was the relationship with your ex, to begin with? Were you in a serious, long-term relationship which you agonizingly decided to end, or was it just a short stint during which you realized you were just not that into each other and mutually called it quits? Because chances are, if it’s the latter, your ex won’t even care that you’re trying to get with his friend; he might even offer to help you! If things were serious, however, you need to watch out, because he will most likely be a little hurt, or at least, confused.

 

Pro tip: If the break-up is “fresh”, give it a few months; no one wants to see their ex moving on so quickly, particularly not with their best friend.

 

4. This brings me to my next point: how was your relationship with the best friend, previously? This question is important for a number of reasons:a. It helps you assess whether or not you would be compatible – were you friendly? Did you have stuff in common? Did you get along well? This is the perfect opportunity to look at it objectively and decide, based on past experience, if you make sense together and if you actually like him, as a person.b. It might lead to some trouble with the ex – for example, he might think that the two of you fancied each other the whole time or that you were together behind his back, cheating on him, etc. So if this was an accusation that has come up before from his part, maybe jumping on his best friend is not the best idea, especially if the break-up is relatively new. That might spark feelings of intense jealousy and even physically aggressive reactions, particularly towards your new beau.

 

5. Whatever you do, tell your ex-boyfriend beforehand – It’s the mature and honest thing to do, for everyone involved. Say you have established contact, he knows you like him and he has given signs that he is also interested in you. You might think the job is done and that you have solved your dilemma of how to date your ex-boyfriend’s best friend. Not so fast! You’ll have to tell your ex, first.

 

Pro tip: Preferably, the two of you should tell him together that you want to date. This is not asking for permission as much as it is informing him, so he doesn’t get blindsided.

 

6. Keep in mind that you might both (you and the best friend) lose your ex as a friend. Sure, he could take it well and have no problem with the two of you dating. Or he might feel really betrayed and stop speaking to either of you altogether. What now? Depending how strong his feelings are, the best friend might decide to stick with you and hope for the best or he might ditch you in favor of his friend, realizing it’s not worth destroying a friendship for a chick. Either way, you’re going to have to be ok with it. It’s not ideal, but you knew this was a possibility, right from the start. You took a chance for love and this is the consequence you have to accept.

 

7. Even if you do get the green light from the ex-boyfriend, proceed with caution. What this means is that maybe you shouldn’t parade your new relationship around in the ex’s face or start a really intense make-out session while you’re out with a group of friends which includes him. That’s just awkward for everyone involved.Pro tip: Don’t mention your ex in front of your new boyfriend. It’s true that he’s a person the two of you have in common, but no guy wants to hear about previous boyfriends. Especially if they know them (or they’re friends!). Especially in bed. You have been warned.

This is how you proceed when you are wondering how to date your ex-boyfriend’s best friend without the guilt. Advance slowly, think about it every step of the way and treat everyone like adults and you should all be just fine, including the ex-boyfriend’s ego.