How Do you Tell Your Best Friend The Guy He’s Seeing is NO Good?

Dear Tavion,

The problem I’m having lately is with my best friend and the guy he’s been dating.  See my best friend is one of the sweetest guys in the world. He’ll do anything for you, is always there when you need him, and always tries to see the good in people.  Me on the other hand, I’m not so trusting of people, and I’m definitely not so trusting of my friend’s man.  My gut tells me this guy is using my friend.  From what my friend tells me, every time he and this guy go out, my friend always pays.  The guy doesn’t even offer.  I also found out that my friend recently paid for this guy’s phone bill. I want to scream to my friend he’s being stupid and probably being used because he has some money, but my friend can be sensitive sometimes. Last time I tried to tell him about a man he was seeing, he got upset and we didn’t speak for a few days.  Keep in mind that I was actually right. How do I handle this situation this go around?

-Philly Tommy

Dear Philly Tommy,

Thanks for writing to me. Based on what you wrote, it sounds like you’re trying to be a great best friend, even if you don’t think your actual best friend will appreciate it.  It also sounds like you may have a history of placing yourself in the middle of your bff’s love life, which can be a bit of a problem. Let’s jump right into it.

I think it’s natural for people to want to protect their best friends.  Heck, if your bff is anything like my bff, you view this person as family.  And most people don’t want anyone coming sideways at their family. I get it. So when this new guy in your bestie’s life strolls in and “takes advantage” of him, your instincts kick in and you’re ready to protect him.  Almost as if you were the mama or papa bear to his cub.  But the thing is, you actually don’t have any parental rights over your ride or die.

I’m going to assume everyone in the above scenario is grown.  Having said that, your friend is old enough to make his own choices and learn from them. And while you just want to protect him from harm, he may need to experience making bad decisions so he can learn from them.  Unfortunately, when it comes to lessons of the heart, the absolute best teacher is life and personal experience.  Which means, we as people have to date the bad guys and kiss the frogs, and hope we learn and mature in romance. Key word here being “hope.”

And I don’t care what anyone says, we’ve all had to learn from our mistakes in love, including both you and me.  Heck I can recall a few times where my friends tried to caution me about dating the stunt queen, the liar, and manipulative user. Did I listen? Nope, I sure didn’t.   However, I soon learned my lesson, and I’m sure you did too going through your own experiences.  Give your friend a chance to mature when it comes to his personal life. It may take him a few tries to get it right, but some folks are what my grandma calls hard-headed.

Now I’m not trying to cause friction in your friendship, but I think it’s odd you two can’t be open and honest with each other.  That you can’t tell your friend he’s making a mistake without him catching feelings and getting upset.  I don’t know about you, but I don’t want to have to sensor myself around my best friend. Although, I’m inclined to think your friend has more of an issue with your delivery of the truth than the truth you’re actually giving.  And if that’s the case, that boils down to your communication skills, and that’s something you’ll want to work on.

Suggestions going forward.

  1. Politely express your concerns to your bff if you think the guy he’s seeing is a real threat to your bestie’s pocket. You could say something like: “Hey man. I’m not trying to be in your business, but make sure this guy is giving to you as much as he’s getting. You deserve to be treated like a king too.”  A statement like this is honest and shouldn’t come off too abrasive.


  1. Once you plant the seed, don’t bring up your concerns about the guy anymore. Back off and let your friend learn his lesson.


  1. If your bestie gets offended by you stating your opinion in a polite way and tone, then you may want to evaluate the relationship you two have.


  1. Remember, at the end of the day, your friend’s love life is HIS to live.


  1. You may also want to consider that your friend likes to play “keeper” to the “kept.” Some individuals  like taking care of their partner. If that’s the case, you ‘ve got to butt out completely.

As always nothing but love,

Tavion Scott

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