
What A Supportive Friend Actually Does (It's Not Quite What You Think)

Thanks to the current season of Insecure, all you've got to do is hop onto Twitter—Black Twitter, I mean—put in the words "Issa" and/or "Molly", and you're going to see a real-discussion-sometimes-war about what it means to have a real friendship. A good example of what I mean is Exhibit A.
It took Andrew to make Molly look around and see that issa was actually working and not bullshitting.
Your man rooting for your friend, another black women, more than you. Embarrassing.
— Come one... Come all 🗣️ (@hearyehearye_) May 14, 2020
Shoot, everything has actually gotten so intense to the point where executive producer Prentice Penny has come to the defense of Molly in the article, "'Insecure' Showrunner: Season 4 Backlash Against Molly Is 'Unnecessary'". Hmm. As someone who has been an avid watcher of the show, pretty much since day one, I've gotta say that "unnecessary" is a bit of a stretch (more on that in a bit). Then there is Issa Rae, the show's co-creator and her take on their dynamic. In one interview, she said, "They are friends, they are real-life friends, but there exists a specific dynamic in their friendship that both of them have gotten accustomed to. They're college friends who have taken on different paths." Real friends. That's an interesting conclusion to me as well.
I don't know about y'all, but I personally think the reason why a lot of what Issa and Molly have going on has us so triggered is because (thanks to this season's impeccable writing) we either have experienced what they are going through before or, perhaps we're recognizing that the Issa or Molly in our lives has us putting up with more than we actually should. And while their relationship has a billion-and-one takeaways, for me, I think what stands out, quite possibly the most, is it seems like they both could stand to gain a bigger grasp on what it means to be a supportive friend in someone else's life; especially if you profess that they are your best friend. If you give me a sec, I'll unpack a bit more where I am coming from by sharing some thoughts on what a supportive friend should actually do.
A Supportive Friend Makes You Stronger
While I'm not going to make this entire piece about Issa and Molly, I do think they both apply to my first two points really well. On the "make you stronger" tip, to tell you the truth, I think it's Issa who could stand to remember this particular point. Although Molly really has showed her ass in a lot of ways, one area where I totally get where she is coming from is Issa doesn't seem to be the most self-aware person on the planet. There have also been times, throughout all seasons of the show, when she comes across as extremely entitled and selfish, like when she automatically assumes that Molly is going to pick up the tab while they're out (like after the Kiss 'n Grind or when Issa wrecked her car and they went through a drive-thru to get something to eat). For Molly to get to the point where she is like "enough is enough" and "grow TF up" with her bestie, that doesn't make her evil or a bad person. It's just that her timing sucked in choosing to do it when Issa was in a bind. Plus, I'm not completely convinced that Molly's motive was pure. Without a doubt, she is passive aggressive as hell, with EVERYONE. She also isn't wrong in her eyes, hardly ever. But more on that in the second point.
Anyway, for Molly to want to pull back some so that her friend doesn't always treat her as her "get out of jail free card" is a form of being supportive, because if someone is always your crutch, if they are always enabling you, how are you going to mature and evolve?
The animal kingdom has all sorts of examples of mamas who, after a time, leave so that their babies can learn how to survive on their own. If we want our friends to be able to stand on their own, sometimes that means telling them "no". Not out of spite, but out of the sincere desire for them to embrace their own capabilities. That's one of the ways that all of us become stronger individuals.
A Supportive Friend Challenges You
If I had to choose between describing myself as being aggressive or passive aggressive, I'm definitely rocking with aggressive. I don't say "I'm fine" when I'm not (or act like things are fine when they aren't). I don't hold things in while waiting for someone to read my mind. I don't seek out to emotionally punish people who hurt me. Sarcasm isn't my first language. I'm not big on giving people the silent treatment. Meanwhile, Molly? Let me tell it, she's about all of these things. And since she sucks at being forthcoming about her feelings, wants and needs—and/or acts like folks should just automatically know about them—by the time she's suppressed to the point of being fed up, she comes across as mean…if not almost evil. She was like that with Jared (the Enterprise manager). She was like that with Jidenna's character (the lawyer). She was like that with Dro. She was like that with her dad when she found out that he did the same thing that she did (he cheated while she helped someone cheat). In this season, she did it with Issa (and she tries to do it with Asian Bae, Andrew). In fact, while I can't remember where I read the comment, a man by the name of Walt Bionick brought up another great point about how Molly tends to get down when he said, "Molly is the kind of person who invalidates your feelings if they conflict with her feelings." (I mean...)
Then, whenever all of these people bring to her attention that she could stand to look at herself and acknowledge that she's the clear common denominator in her relationships, she goes on the attack and acts like a victim (when Andrew apologized to her for helping out who is supposed to be her friend only "babied" her more into her toxic coping mechanisms, if you ask me. *le sigh*). Indeed, if anyone is the walking definition of not being able to take what they and their sharp tongue can dish out, it's Molly. Hmph. Perhaps if she listened to the people who truly cared about her, it could help her to get out of the cycle of constantly suppressing and then being resentful to the point of sabotaging so often—and so much.
Believe you me, some of the biggest "ouches" I've experienced have come from people who loved me enough to call me out on my ish. Anyone who thinks that a supportive friend shouldn't do that might want to mosey on over to Proverbs 27:6(NKJV) where it says, "Faithful are the wounds of a friend, but the kisses of an enemy are deceitful." I once read that this means a real friend will tell you about yourself without broadcasting their views to others because their intent is to challenge you to become a better person without putting you on full blast in the process. A mature individual will get that this is a form of support because if you only want people to see you as you do, there will probably be blind spots that will certainly hinder your progress—if not now, eventually. Friends want to see their friends thrive in life. Growing pains can be hard, so we have to be challenged, sometimes by our friends, along the way.
A Supportive Friend Is Lovingly Rather Than Brutally Honest
As direct as I am, personal growth is teaching me to dislike the phrase "brutally honest" more and more. I know folks are out here bragging about being savage and everything, but goodness—that is a really harsh word. While savage can mean "fierce", cruel, uncivilized and criticizing to the point of not knowing when and how to let up define it too. And you know what? All of this defines what it means to be a brutal individual. And who would want a friend, someone who professes to love and care about another individual, to speak from this kind of head and heart space?
I don't care if it's advice on a relationship or job, offering up some news that can be difficult to hear or being frank with someone about their personality or character, a supportive friend isn't going to lie. At the same time, what they also aren't going to set out to do is be honest in a way that ultimately does more harm than good. After all, one definition of support is to hold someone up. How can you do that if your words are so damning that all you actually end up doing is tearing your friend down?
A Supportive Friend CONSISTENTLY Wants to See You Win
One of the reasons why I wrote articles on this site like, "5 Signs Your Closest Friends Are The Most Envious Of You", "6 Signs A New 'Friend' Is Nothing But An Opportunist" and "10 Signs You've Got A Close (TOXIC) Friend" is because, make no mistake about it, deception is real, alive and kicking out in these streets. And the thing you've always going to remember about deceit is it's designed to look like the real thing…even though it's nothing more than a fraud.
How can you know when someone who claims to be a friend of yours is anything but? One sign is if they don't show any signs of wanting to see you win in life. You set goals and they automatically look at the obstacles—whether real or actualized—in order to discourage you. You ask for help and they are rarely available to assist. You end up with something (or even someone) that they wanted and they aren't enthused, they act shady or they even completely go ghost on you. It's like, so long as they are on top or you are "in the struggle" it's all good. But when success is within your grasp (or you've obtained it), now there's a problem. And that? That is a problem. By definition, a supportive person encourages, a supportive person helps, a supportive person rallies on your behalf. You know what else they do? They celebrate you in your wins. Not every once in a while, either; consistently so.
I've had some people in my life who wanted to be there so that I could support them. But when it came to me and my needs, I couldn't name one way that they were of assistance. That is wack. That's also (one of the reasons) why I released them too. A good friend is a great cheerleader. If you've got a "friend" who you can't say that about, I'd encourage you to rethink the role and position that they play in your life.
A Supportive Friend Loves You in Spite of Yourself. Period.
Is it just me or would it be super shocking if Insecure's Tiffany was hiding a secret about her baby, Simone? As a doula, while I must say that they are penning postpartum in a really realistic way (bravo!), Tiffany has always seemed to have a shady side to me. I mean, she did know that Lawrence and Condola were dating and didn't let Issa in on it. I also remember when her husband, Derek said he had to get "rid" of the co-worker Fred. Plus, Tiffany once said they had separated before but didn't want to talk about it (dun, dun, dun, dun). Chile, we shall see. But whatever is up, if there is one thing that the girls—Issa, Molly, Kelli and Tiffany—at least strive to do (even if it isn't always perfectly) is love one another…warts and all. Just as a supportive friend should do.
I don't know about you, but I've been in situations where I thought I was in a friendship. However, those people only acted like my friend so long as I had the same views, did the same things or approached life in a similar way to them. But when I wanted to do my own thing, even if that meant making some mistakes along the way, it's like I was penalized, if not emotionally punished for it. That made me want to be my authentic self with them less and less—and when you can't be genuine with someone, the relationship ends up being pretty unhealthy. And unhealthy eventually becomes unnecessary.
Another definition of supportive is sympathetic. That's when someone tries to understand how you feel. It's also when they extend compassion whenever possible. If your friends ain't doing that, if you're not doing that for your friends, support is severely lacking. And if you're not able to lean on each other and have each other's back—really, what are y'all doing? Why do you even call each other "friends" to begin with? Because, if at the end of the day, supportive isn't a top defining word for your friendships, it really is time to shift—possibly even move on. If anyone runs into Issa and Molly, relay the message, OK? I appreciate it.
Want more stories like this? Sign up for our newsletter here and check out the related reads below:
What If You Love Your Friend...But Don't Like Her Anymore?
Always Remember That Friendships Have "Levels" To Them
Featured image by HBO/Insecure
It's kinda wild that, in 2025, my byline will have appeared on this platform for (what?!) seven years. And yeah, when I'm not waxing poetic on here about sex, relationships and then...more sex and relationships, I am working as a certified marriage life coach, helping to birth babies (as a doula) or penning for other places (oftentimes under pen names).
As some of you know, something that I've been "threatening" to do for a few years now is write another book. Welp, October 2024 was the month that I "gave birth" to my third one: 'Inside of Me 2.0: My Story. With a 20-Year Lens'. It's fitting considering I hit a milestone during the same year.
Beyond that, Pumas and lip gloss are still my faves along with sweatshirts and tees that have a pro-Black message on them. I've also started really getting into big ass unique handbags and I'm always gonna have a signature scent that ain't nobody's business but my own.
As far as where to find me, I continue to be MIA on the social media front and I honestly don't know if that will ever change. Still, if you need to hit me up about something *that has nothing to do with pitching on the site (I'm gonna start ignoring those emails because...boundaries)*, hit me up at missnosipho@gmail.com. I'll do what I can. ;)
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Are You & Your Partner Financially Compatible? Here’s How To Tell.
With nearly half of all marriages that end in divorce citing finances as the nail in the coffin to deading their relationship, financial compatibility is one aspect of long-term compatibility that doesn't get talked about enough. Beyond the circular 50/50 discourse and whatever hot-button issues regarding providers and the like, at its core, financial compatibility is about how well your financial behaviors, values, and long-term goals align with those of your partner.
More than it is about how much money a person makes or doesn't make, financial compatibility focuses on how you think about money, how you spend your money, and most importantly, how you plan for the future with your money. Think, questions about money mindsets, spending habits, debt, budget, etc. Are you a saver and he's a spender? Do you see money as a tool for freedom? Does he see it as something to hold on tightly to as a means of survival? Can you talk about your financial goals and plans openly?
Knowing if you and your partner are financially compatible can save a lot of heartache, a lot of headaches, and a lot of money in the end. Keep reading for a few key indicators to pay attention to and learn whether or not you and your partner are truly aligned financially.
Signs You’re Financially Compatible
1. You can talk about money without judgment.
Conversations about money aren't something you dread. You're able to talk to your partner freely and openly about money matters, like debts, bills, the budget, etc., even when it is uncomfortable. There is an understanding that talking about money doesn't have to be something you're on the defense about, instead it's an opportunity for transparency, clarity, and solutions.
2. You respect each other's money personalities.
What is a money personality? According to Ken Honda, author of Happy Money, a money personality is our "approach and emotional responses to money" and there are seven money personalities we can fall under. These personalities can help us understand our own relationship with money, as well as our partner's. For example, maybe you're someone who likes to treat yourself to a fancy dinner once a month and your partner is someone who believes ordering takeout and not cooking meals at home is a cardinal sin.
When you can respect each other's money personalities, neither approach is subjected to judgment and shifts can be made in each other's spending habits as needed and from a place of love versus guilt or shame.
3. You agree on what it means to have "financial security."
Whether it’s building a stacked emergency fund, paying off debt before putting a downpayment on a home or being able to splurge on a baecation without checking your account balance before the bill arrives, your definitions of what it means to be financially secure are in sync, or at least compatible enough to reach a compromise.
4. You are not each other's "financial parent."
You’re not constantly teaching, fixing, or stressing out over what the other person is doing with their money. Although I fast-forwarded through a lot of the most recent season of Love Is Blind, I did pay attention to Virginia and Devin and money seemed to be a recurring theme in their conversations. It was clear Virginia had her ish together when it came to money and her financial plans for the future and Devin was not quite on her level.
Though she said no at the altar for additional reasons, I could also see how sis could eventually get very tired of being her partner's second mama, so to speak. And that's the thing about being your partner's "financial parent," eventually, you could end up feeling like you are one-half of a "parenting" or "teaching" dynamic with your partner instead of feeling like you're equals in a partnership.
5. You make financial decisions with each other in mind, not for each other.
Whether it’s booking a trip, deciding which debt to tackle first, saving up for a big purchase, or planning out your next move, there’s a mutual respect for each other’s input. Those shared goals might look like wealth, freedom, stability, or just a debt-free life that feels soft and secure.
You don’t have to be chasing the same bag in the same exact way, but you do need to be aligned on the vision. What you're building should feel like a joint venture with shared effort and purpose, not one of y’all making major money moves like you're still single. Making financial decisions is not just about where the money goes, it's about where you’re going together.
6. You're aligned when it comes to the big stuff.
Financial compatibility extends to the long-term of money management. The legacy, structure, and shared responsibility that comes with decisions like shared accounts, estate planning, having babies, or even blending families. Will you split bills or combine income? Who’s taking time off if you have a child? How do y’all feel about generational wealth or investing for your family’s future? You and your partner have had the real conversations.
These conversations can’t wait until after the wedding or until after a baby’s here. They’re the foundation for how you function as a unit, and if you're not aligned, or at least willing to get on the same page, that incompatibility can cause friction in the end that love alone can't fix.
Love is cute and all, but building an empire together? That’s the real flex. Tap into our new series Making Cents to see what financial compatibility really looks like when love and legacy go hand in hand.
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