15 Reasons To Flirt With Your Best Friend's Boyfriend

Flirting with your best friend’s boyfriend seems like a pretty controversial topic. But when we take a closer look, we realize that it’s not as taboo or scandalous as you might think. Remember, we must look at the situation from more than one perspective. Have I piqued your interest? If so, let me dazzle you with what situations you could get away with flirting with your best friend’s beau. It might seems tricky, but once you read the article, you’ll have a better idea of how and why to do it. Consider this your Intro to Flirting 101: The Best Friend’s Man Edition. It’s not so uncommon to flirt with your best friend’s man either.

There’s no need to feel ashamed at this point. The fact that you’re reading this article means that you are into him. Whether you are into him for some gratification or for another, deeper reason, then just be honest with yourself before taking the plunge. There’s nothing wrong with breaking social norms as long as you’re certain about your intentions and, more importantly, as long as you’re certain that you won’t hurt those around you. Although, if you deliberately want to hurt your best friend to get even, then this is as good as any action to take – and it will get you the results you seek.


15 If your best friend is cool with it

Relationships between besties can be really quite unique. Case in point, if your best friend is alright with you flirting with her man – or maybe even likes it. She doesn’t even need to have a specific reason. She just for does. Or maybe you’re the kind of friends that share everything, so there is no jealousy between the two of you for any reason, especially not for a man. If your best friend is cool with you flirting with her boyfriend, and you are 100% sure that it won’t cause any drama between the three of you, then sure, go for it. But like the seasons change, so do we. So be mindful of the possibility that your bestie’s attitude on the subject might change. Just be prepared for it and pull back if need be. Don’t get all stuck on flirting with him when there are plenty of men in the world to flirt with.

14 If both of you are into that polyamorous thing

We have long held monogamy as the standard, only to realize that human beings have been polyamorous since, like, forever. It became more natural for us to have multiple lovers at the same time instead of devoting ourselves to just one person. That concept surfaced when religion was created. So maybe you and your best friend are so liberal that you realize you can love different people at once – and all without anyone getting hurt. Well, that’s good for you two because not everyone is that open minded. If you two are ok with that, fine, go with the flow, and enjoy that lifestyle. To each their own. But make sure that the people you are involved with are also into that sort of lifestyle. If your best friend’s boyfriend is a one woman kind of guy, you might just end up complicating things between the three of you.

13 If you know your best friend is cheating on him, and you’re interested in him

She maybe your best friend, but that doesn’t mean you should support her when she’s been doing dirt – especially hardcore dirt and on a good man. Her boyfriend is a good guy and you know that, but it seems that she’s forgotten how good he is. That’s why she’s out there doing her thing. So if you want to wake her up a little, really shock her into realizing that she’s wrong for cheating, then flirt with him. If she seems unresponsive, like she doesn’t care, then she might not care for him at all. She might be too preoccupied or distracted to focus on the relationship. This might be your chance to swoop in and steal her man if she’s ready and willing to let him go. Remember, one woman’s trash is another woman’s treasure. If you miss this chance, you might never get another one again.

12 If you want to test if he’d cheat on your best friend

This is a classic. Which one of you hasn’t asked your best friend to flirt with your man to see how he responds? We’ve all done this, ladies. While this test isn’t exactly accurate because some men are already onto the game, it does work in some cases. Therefore it’s worth a shot. If she’s doubting his loyalty and asks you to invite him out, flirt with him, and propose a night of lascivious behavior – then you know you’ve got to help her out. She’s in desperate need of help. And as her bestie, you are obligated to help as long as it doesn’t compromise with your own values or lifestyle. Unravel the clues and see if that boyfriend of hers is a sleeper or a keeper. If he is as sleazy as she thought he was, then at least you helped him get rid of her. However, if he is a saint, then you might want to keep it a secret that you and your best friend were just testing him. He might be offended that she doesn’t trust him.

11 If you’re trying to start a fight with your best friend

Looking to start a fight with her? Then here’s a surefire way to get the show on the road. This will be even more effective if your best friend is the super jealous type and doesn’t like it when people talk to her man for more than a few minutes. She’s always got her doubts, which could be a result of his bad behavior in the past or because she’s insecure in general. If you really want to make her more insecure and have trust issues, then start flirting with her man. But be warned that such behavior is bound to end the friendship for good. Because if she’s really your best friend, even if you two had a fight, there’s no reason to push her to the edge, try her patience, and make her even more insecure. That is just plain cruel. Take your time to think before you act on this one.

10 If he’s more like your buddy than your best friend’s boyfriend (innocent flirting)

Maybe it’s completely innocent. You might not even call it flirting. And neither would your bestie. It’s just you and him are like kindred souls or something – like you just vibe. But the flirtation has no sexual undertones. It’s more like both he and your best friend are your besties. There’s a solid bond between the three of you. And you're flirting with him is completely platonic. You look at him as though he’s your brother and nothing else. If everyone involved is clear about that and there are no mixed messages, then this type of flirting is A-Okay. But like we’ve mentioned earlier, if it reaches a point when your best friend suddenly finds this situation uncomfortable, then keep your distance right away. After all, no matter how close you and this guy are, he’s still your best friend’s boyfriend.

9 If you’re trying to get a trio going

When you catch yourself flirting with your bestie’s boyfriend (even with your bestie, at times) all of a sudden, this might be your subconscious’ way of saying that you want to engage in a threesome. Girl, there’s no point denying that you’re into that freaky stuff and that’s cool. Roll with it. Embrace it. Or maybe it’s not your subconscious talking and you know exactly what you’re doing. You have been plotting this scenario the entire time. Maybe you’ve talked to your bestie about it or maybe not, but it’s something you want to see go down. Perhaps you might want to talk to your bestie first before you set any wheels in motion. After all, hoes before bros. So don’t start something without her permission first. Because you never know what her stance is regarding these things. You’ll thank me for this later.


8 If your best friend asked you to do it, she’s into voyeurism

Is your bestie into watching others get it on? Like watching others in sexual scenarios? Well, if she’s asking you to flirt with your man because she likes to watch, chances are your bestie is a voyeur. She might not even realize it. If you’re down to help her get her game going, then go for it. Why not? It will be fun for all involved, as long as it stays between the lines. Ask your bestie what she wants from you, what she hopes to witness, and what she desires from this interaction. Make sure everything is clear, otherwise you might run into some problems that you didn’t foresee. It’s best to be straight up honest from jump, that way no one gets hurt. Most importantly, also make sure the guy is into this scenario, as well. This way, all of you are on the same page.

7 If your own partner is into it, again for excitement sake

Like your freaky bestie, your own partner is into watching you flirt with others. And it’s not just with her best friend’s man either. Your partner wants you to flirt with everyone, actually. But he feels most secure when you flirt with a man who is already taken. To him, it saves him the hassle of worrying about cheating. (Little does your partner know that many affairs happen between friends and close acquaintances, but don’t tell him that. Let him believe whatever he believes.) As long as everyone involved is ok with the scenario, there appears to be nothing wrong with a bit of group flirting. Be prepared that this might lead you all down to a swinger’s path, but if you’re cool with that, then there’s nothing wrong with it at all. But considering you are engaging with more partners than usual, make sure you stay protected.

6 If your bestie isn’t as committed to him

If your bestie is just with this guy temporarily, like she’s already told you that she doesn’t see a future with him whatsoever, then, girl, here’s your chance to let your feelings be known. It doesn’t have to be overt or even in-your-face type of flirting. It can be subtle, it can be small signs of affection or gestures to let him know you are interested. You already know your bestie is going to let him go, but you don’t want him to walk away and get lost for good. You also don’t want to get lost in the crowd, the sea of woman that seem to dance around him. He’s a catch and you want to be sure that you’re next on his list. Since your best friend isn’t even that invested, she shouldn’t mind if you flirt. Actually, she should welcome it and see it as a way to finally get him off her back. But before you make your move, make sure you are on the same page with her, just to be cautious.

5 If y’all don’t have any problems with flirting because it’s just flirting, after all

You aren’t bound by any categories or form of jealousy. You are all well aware that flirting is just flirting in most cases, and should it lead to more, then so be it. Basically, you enjoy living on the edge and you like it that way. The fact of the matter is that flirting is healthy, so your best friend, her partner, you, and your partner are free to flirt with each other. It’s a good way to build up sexual tension as well as trust between all parties. Flirting shows more than just sexual interest, it demonstrates care and concern. So since y’all already knew that, this entry is null and void. Keep living that liberated life, breaking free of boundaries, and focusing on light and love. Who cares what anyone else thinks? As long as everyone is enjoying themselves, then there’s no problem at all.

4 If you want to end the friendship

Want to say goodbye for good to your best friend in a cruel way? Then by all means, start flirting with her boyfriend without any restraint or shame and your wish will soon become reality. When you approach another woman’s territory, things can get ugly. You and I both know this. Women are territorial by nature. After all, no matter how advanced human beings are, we are still part of the animal kingdom. If for some reason, you need to call it quits with your bestie, then this will get the job done. Be warned, though, that if you’re looking to repair things with your best friend in the future, it will be difficult after doing this (but not entirely impossible). You are making a bed into which you will sleep on – so be prepared for all of the consequences that come along with this act.

3 If you’re practicing your flirting skills

Maybe you need help in the flirting department. Many of us might agree that flirting can be tough sometimes. And with technology so advanced, flirting face to face has never gotten more confusing. So why not practice flirting with your best friend’s boyfriend? The beautiful thing about this is that there is no danger of anyone getting hurt. All you want to do is learn some flirting skills. Ask your best friend to be present while you try your hand at the wonderful skill of flirting. Feel free to ask for constructive criticism that can help your next flirting lesson. And with this arrangement, you also get unrestrained input from a male perspective. You could use this to your advantage once you find someone you really like. As long as everyone involved knows the objective, this reason is the most harmless one on the list thus far.

2 If you have an innocent crush

So he’s cute - Ok, he’s really cute. And it’s hard not to flirt with him. He’s also charming AF. You’re not the only one who sees this either. Tons of women flirt with him – all the damn time, actually. You’re not sure how your best friend manages it all, but she does. Maybe they have some secret agreement that she’s not yet told you about. But there is something totally irresistible about him, and every time you’re around him, you act like a silly, little school girl. You have a crush and it appears that you’re not alone. We all have crushes that come and go. Don’t feel too badly about this one. And don’t get your panties in a bunch if it seems like your bestie is already hip to the fact that her man is a charmer. Perhaps a little flirting is all you need to scratch this itch.

1 If you give zero f*$#s

Are you just one of those girls who likes to live on the edge? Then F it, go ahead and be as careless as you want to be. Flirting with your best friend’s boyfriend without any consideration for her feelings or what it might do to their relationship is selfish and crazy AF. If you’re all about that life, and you think you can find another bestie in a heartbeat, then this is no reason not to flirt. It’s probably the dumbest reason of all, but if you’re totally stuck on that Bad Girls Club lifestyle, and you are void of feelings, go for it. Your lack of humanness will eventually seclude you far, far away from real humans and you will finally understand, hopefully, all the hurt you’ve caused throughout your lifetime as a result of living a selfish life. That do-whatever-I-want to-do attitude is so exhausting – and so will you.


More in Love