A Gentleman's Guide





Almost all of us can attest to having that one problematic friend. He’s the friend who’s late to everything, arrives empty handed, and the one who is as pessimistic as they come. He’s dramatically inappropriate, low key prejudice and while you’re not one hundred percent certain, you’re almost sure he’s transphobic as hell. His expectations are unrealistic, he’s constantly complaining and can almost always be found in the midst of some kind of drama, gossip or argument. He’s the living embodiment of the word as he is difficult, always in the mood to be disagreeable, and has somehow found time to master the arcane art of being simultaneously loud and wrong. We know the problematic friend, hell, some of us are the problematic friend. The behavior is easy to identify to some but isn’t always spotted by the radars of others which is why we’re dedicating this month’s Front Page to identifying some problematic behaviors and some ways in which they can be dealt with.  

The key to identifying any issue is to define it, so it should come as no surprise that we’re about to hit you with the definition of the word. Problematic, as a term is over used but at its core represents anything that presents, encourages or promotes difficulty. The word found its second wind in 17th century French, but originates from the Latin “problematicus”. However old the word may be, the behavior that defines it is as old as time, and can be viewed as either subjective or objective. If you’ve been following us for a while you know we’re going to tackle this topic objectively.

Before we dive into ways to address problematic behavior, we should all be aware that the only reason we find anything to be problematic is because we disagree with it, and that’s our problem. Again, we’re looking at this objectively, so if we find ourselves bothered by a video from Walter Lee Hampton or a tweet from Candace Owens, we’ve got to own up to our own emotional investment in the situation. It is for this reason that our first suggestion in confronting problematic behavior is to confront the way the behavior affects us. This is the ‘why’.


Problematic is problematic, and the first step towards dealing with it is to identify our connection. We’re going to need to explain this when we confront Tyrone and his consistently pessimistic ways.The next step is going call for us to be able to produce as many receipts as possible, so we’ll need to remind him of why we don’t like being called “gurl”, or “sis”. We’ll need to let him know why we’re pressed about him doing it for the gram at XIX Nineteen, and why we’re bothered when mentions how skinny we might be.

We know the why the whys bother us. We don’t like being called ‘sis’ because we’re men, and while the term might fly with other, its got no wings here. We lent him that money in good faith, and the fact that he hasn’t paid it back is indicative of him taking advantage of us, and we can’t help that we’ve got a high metabolism and are already internally struggling with our weight in the age of thickness. Regardless of what the problem is, its a problem, and it needs to be addresses crucially and in conversation.

So how do we summon the courage to have a crucial conversation with our problematic friend, and what do we need? We’ve already talked about the first two things we need, which is a problem (or problems, depending on the situation), and a list of receipts. With respect to the third thing we’ll need, well, you’ve just read over that--courage. Let’s assume that we’ve got our problem, receipts and our courage. Where do we go from here?


A good place to start is with other friends. Ask them. Does Tyrone treat the rest of the friends in our circle like this, or is it just us? If the consensus is that he treats everyone like this then we can find relief in his behavior not being personal, but if it we discover the opposite then we’ve got more problems than previously anticipated. Either way, we’re going to use the information we’ve gathered from the mutual friends we share with Tyrone and add it to our arsenal.

The next step to this process is to figure out exactly what we want. What do we hope the outcome of the conversation will be? Changed behavior? An apology? What is it that we really want to happen for us and our relationship with our problematic friend? A word to the wise would be to never advise a friend on what we want them to do moving forward, because we’re only responsible for how we operate moving forward. Hopefully they’ll listen, as any true friend should, but if they aren’t interested in making these changes for the sake of the friendship then we need to decide if we’re going to continue the relationship or completely dissolve it. ***

And now, (drum roll please) for the conversation. Okay, we can do this. We. Can. Do. This! A conversation as crucial as this requires for us to step outside of our comfort zone, because conflict is never comfortable. Make sure that the conversation takes place in a neutral zone and in private. This will assure that we’re on the same level as our problematic friend. Starbucks is almost always the safest bet on account of it offering an atmosphere that will more than likely prevent either of us from getting out of control and in that they don’t serve alcohol. Also, since this is essentially our problem, it's only fair that we pay for whatever bougie drink our friend wants to consume.  


Remember to start from the heart. Starting from the heart is entering the conversation with a goal and an understanding that the goals we’ve set may not be met. Remember the problems and remain clear on why they affect us.Consider what it is we really want this conversation to achieve

So we’re face to face with Tyrone, who’s already greeted us using a female pronoun. Exchange pleasantries, buy the drinks, find a table and then lay it on him. We start from the heart by telling him about our concerns and share what’s true for us. We’ll mention the misgendering, the money and comments he makes about our weight. We’re going to pull receipts which shouldn’t be too hard because he “sis’d” us about ten minutes ago, just posted another picture of him eating at a fancy restaurant, meanwhile April’s debt still remains. We’re going to use this opportunity to share our story, We don’t want to make this one of those “lead-with-your-pinky”, conversations, but we do want it to be one that gives us the opportunity to express the ways their behaviors lead us to feeling and the impact they have on our relationship with them.

One thing a lot of us tend to forget about communication is that it is a two way street. Conversations are communication, so we need to remember that we’re not talking to ourselves and allow space for our problematic friend to interject and, if possible, defend himself. Maybe he didn’t know these things were problems for us, that he was just acting in a way that comes natural for him. We’ve got to allow him the opportunity to say his peace, Some of us might know what its like to make a joke and accidentally offend, but the only reason we know we’ve offended someone is because they told us. We’ve got to give others that same opportunity and remain open in our belief that maybe, just maybe, Tyrone didn’t know that any of this was a problem to begin with.


While conversation is key, it’s important to set some expectations. Let’s say that everything goes well with our conversation with Tyrone. What’s next? Again, this isn’t about what we want them to do for us, it's about taking steps to make sure the relationship stays in tact. This might mean instituting the “ouch” “oops” rule where the person committing the offense yells ouch, while the other, in acknowledgement of the offense responds with “oops” This is a great example of us working with Tyrone in being mindful of the things he says or does as opposed to him constantly working to make sure he doesn’t say or do anything problematic.

So in the event that we do have that problematic friend who we can only take in small doses, remember that he’s our friend for a reason. Whether he mirrors some of our most endearing personality traits, adds balance to our personality or has shared a personal trauma or experience with us, he’s our friend for a reason. This doesn’t mean that he can’t be problematic.He’s cheap, has a foul mouth, and he’s late to everything -- but he sent the biggest bouquet of flowers to our mother’s funeral, will take a bullet to the head before he lets us down ourselves and is the only person we know who can quote Jackie’s Back word for word. He doesn’t judge us, and though we’re not going to excuse his problematic behavior, we’re not going to judge him, either.

As problematic as this friend may be, we owe these crucial conversations to him because chances are he’s not being problematic on purpose.  Remember to identify why the behavior bothers you, to operate on facts and not feelings, and to softly interrogate your mutual friends to see if you’re the only one in your feelings. Make sure that you not only identify what you want to gain from the conversation, but that you’re prepared in case the entire thing goes left as well. Be mindful that the goal should be one that involves you both, and not one that requires your friend to do all of the changing.

Remember to inquire within first, to identify why the behavior bothers you and to ask your mutual friends about their interactions with your problematic friend. Couple these things will setting an intention for the conversation while simultaneously staying in tune with the reality that the outcome may not be what you expected. Refrain from entering into this with a one sided perspective, because relationships require both parties to bend, and expecting a one sided behavior change is as unfair as it is unrealistic. Lastly establish a safe word. Remember how Issa and Molly got into that fight after all the tea was spilled? The two agreed to work towards being more honest with each other in difficult times and implemented the use of the word “Malibu” to signal that one was about to keep it totally one hunned with the other.

Jeremy Carter