
10 Questions To Ask Your Close Friends Before The New Year Begins

Something that I try and do, right around this time of the year, is take an inventory of my friendships. Some folks think that it's weird, but I don't care. When you spend enough time working with married couples, and you see in a very up close and personal way that, oftentimes what tends to cause the breakdown of their relationship is either A) they aren't genuinely friends or B) even as friends, they haven't made the time to revisit the needs and expectations that they have, you learn how important taking regular relational inventory actually is. After all, the word "inventory" literally means "to take stock of; evaluate". And why shouldn't you be intentional about evaluating your friendships?
Why do I do it right around this time? There is something about the fall and winter that beckons us to think about where we are in our lives and then ponder how we want to move forward as we prepare to go into the new year. Plus, since a lot of us get to take at least a couple of days off during the holidays, this is also a good time to schedule in some quality time with the homies to make sure that everything's good.
A wise person once said, "A true friend accepts who you are, but also helps you become who you should be." If you want to make sure that you and your friends are doing these things for one another, use these final few weeks of the year to get clarity by asking the following 10 questions—and by allowing your friends to ask you these questions as well. I've done it. It's quite revelatory and beneficial. It definitely helps to bring new light and great insight into where things stand—and that's always a good thing.
1. Are You Happy with Where Things Are?
The reason why I semi-recently penned "What If You Love Your Friend...But Don't Like Her Anymore?" for the site is because, you'd be amazed how many people are stressed out over what to do about some of their friendships because that is exactly how they feel. They love their friend(s), but they don't like them very much (anymore). Once they allow that reality to simmer, either one of two things typically ends up happening—either a huge fight (and by "fight", I mean fall out) occurs, or they end up ghosting the individual.
I've been ghosted by a close friend before. It took me a while to heal from the experience, so personally, I'm not a fan of it. I feel like things can be handled so much better if some communication transpires. More importantly, proactive communication. That's why I recommend asking your friends if they are happy with where your friendship with them currently is. Not if it's perfect because it ain't, but if, overall, they find joy in the connection and contentment in the relationship. If they are, the rest of these questions will basically be a breeze. If they're not, there's no time like the present to hear why they're not so that you can see if anything can be done to change that.
2. What Can I Do to Strengthen the Trust Between Us?
My friends know that, when it comes to the things that I am convicted on, I'm a pretty black-and-white individual; that I see very little grey. I am fine being that way; it's a part of my core. But where I realize that I had to grow was accepting that everyone is not like me; that our perspectives and experiences can result in us coming to different conclusions on various matters. So, while my friends know that I'm loyal when it comes to keeping their business private and holding them down, I had to strengthen the trust bond by making them feel like they could come to me whether I agreed with what they were saying or doing or not. That, they didn't have to worry about feeling berated or attacked for expressing their own journey—even during the times when they knew they deserved better. I had to work on becoming a safer place and space.
When someone trusts you, it means they are confident in knowing that they can rely on you. When the trust between two people is solid, there is very little that they can't get through together. Trust is something that is ever-evolving. It can never hurt to ask your friends what you can do to make the integrity of your bond with them even stronger.
3. What Are the Strengths and Weaknesses in Our Friendship?
This is the kind of question that, if you're an ego maniac or super insecure, it can be hard to hear the answers to. But since one of the purposes of friendship is to help us to become better people, it can benefit you to hear your perceived strengths and weaknesses from the ones who love you most.
Here's why I say that. Recently, I had a rare "fight" with a close friend of mine. She said something, three times in a row, that triggered me to the point that I left her office and went home. I was pissed. Because, in times past, my pride would sometimes cause me to wait until the other person came to me first, and also because I'm working more and more on not letting the sun set on my anger (Ephesians 4:26), I called her as soon as I walked through my door. After a two-hour discussion, we talked about how a strength of mine is stating my needs and how a weakness of mine is sometimes taking out my triggers on the wrong people. I shared that a strength of hers is listening really well and a weakness is not always apologizing when she's wrong.
I'd venture to say that if we hadn't had that chat, we could've had an even bigger blow-up next year. It would be because I wouldn't be using this time to deactivate certain triggers, and she wouldn't be working on acknowledging her offenses. But now that we're both aware, we know how to encourage each other to be better. We know how to build up one another's strengths and help each other to grow where are weaknesses are concerned.
4. What Are Your Triggers? Do I Have a Tendency to Push Them?
On the heels of the last point, while reading an article on emotional triggers, I liked how the author defined them as being, "the surprises that we get when someone we love, or a situation, causes us to have a reaction that we haven't processed yet". When I reflect on my own triggers—and also the triggers of some people that I know—I truly believe that some people have conflict, not because of their relationship, but because they are constantly "triggering" each other. However, once the triggers are brought to the forefront, things are able to balance themselves back out and peace is then restored.
This is why, I most definitely recommend that you and your friends talk about one another's triggers. What they are, where they came from and how to avoid poking at them. Again, there's no telling how many friendships could be spared, just by having this one conversation alone.
5. What Is Something That You Wish We Would Do Together More?
None of us really "have" time in the sense that we're simply twiddling our thumbs and looking for stuff to do. But when you value someone, you find a way to make time for them. No matter what your actual love language may be, all of us need quality time, especially with our close friends. It's a great way to nurture the friendship and, to also be able to spend time together without any distractions.
Something that I like about my friendships is different ones tap into different interests that I have. Yours probably do too. Even if you're only able to get together with your buddies, once a month or, if they live out of town, once a year, be intentional about making plans to hang out. Do something for the first time together. Take a class. Go on a vacation. Do something that reminds you both that, no matter how hectic life gets, you've always got time for each other. And you want to make as many memories together as you possibly can.
6. Do You Think We Make Enough Time for Each Other?
Speaking of time, when you're like me and you're in your 40s and have never been married and you don't have children, sometimes you can find yourself doing most of the work to keep your friendships afloat. At least it can end up being that way until you bring it to the attention of the friends in your life who are married and/or have children. If you're married or a parent and you're reading this, I am confident when I speak for those who don't fit your demographic when I say, "Just because we're not 'your kind of busy', that doesn't mean that we still don't have plenty of ish to do." All people who are living out their purpose do. So, just like you've got to carve out time to hit us up, we've got to do the same.
This was the conversation that I recently had with one of my favorite people on the planet. I had to let her know that, when I looked at my phone, it had been about a month since she rang me, even though we speak a couple of times a week. After I said it, she didn't feel some type of way. She actually acknowledged that she was slipping a bit. Things have been balanced ever since.
Nothing grows when we don't spend time with and on it. And while none of us have a ton of time, for the sake of taking good care of our friendships, it's important that we do our best to make some. More than that, that our friends feel like we are making some just for them.
7. Is There Anything That Bothered You this Year That You’re Holding Onto?
A girlfriend of mine recently told me about how a girlfriend of hers forgot her birthday for the third year in a row. I'm a Gemini and we tend to act like our birthdays are national holidays, so I could definitely feel her pain. When I asked her what bothered her most about it, she said that it was the fact that, prior to three years ago, this particular friend made a huge deal about her special day. So, she felt like it was a passive aggressive way of addressing—or rather, not addressing—some hard conversations that she's had with her ever since her friend got into a toxic relationship.
When I asked my friend if she was going to discuss this with her friend, she said, "No. If she cared, she'd do better." Eh. My take on her resolve is, that's a lot to assume—the passive aggressiveness, the motive behind dropping the birthday ball, and also thinking that she doesn't care. And what's really crazy is her friend may be out here thinking that everything is perfectly fine. Clearly, it's not.
A good article on suppressed emotions brings up a very valid point—"If you don't face suppressed emotions, you'll stay stuck in getting over it mentality, and it'll become impossible for you to heal." If there's something that you're holding onto, tell your friend(s). While you're at it, ask them if they need to get something off of their chest as well. That way, everyone can go into the new year with clarity and a clean slate. No one will have to drag any baggage that came from holding stuff in instead of (respectfully) letting it all out.
8. What Do You Think We Currently Have in Common?
I'm pretty sure you've heard the C.S. Lewis quote that says, "Friendship is born at that moment when one person says to another: "What! You too? I thought I was the only one." Keeping this quote in mind, I've got a male and female friend who I can easily stay on the phone with for hours at a time because we've got so much in common. At the same time, because I'm single, she's married and he's divorced and also because we each live in a different state and do totally different things for a living, our life experiences constantly expose us to new things too.
My girlfriend used to totally consume pop culture; now she's far more into politics. My male friend was a homebody when he was married; now that he's divorced, ole' boy is out there (in about every sense of the word!). As they shift, there are some things that we don't have in common. We're not clones of one another, so that's perfectly fine. But, the reason why I make a point to ask them what they feel that we do have in common is so we can still feel connected via those things, as we give each other the freedom to have other interests with other people too. That way, we don't feel like we're "losing" each other so much as we're celebrating each other's growth and evolution.
9. Are Your Needs Being Met in Our Friendship?
An article that I wrote on the platform that helped me to get my own self free was "Here's Why You KEEP Not Getting What You Need In Your Relationships". One of the reasons why I kept feeling deprived in some of my relationships with people is because I was expecting others to be the kind of friend that I was—to give in the way that I do, to make time in the way that I do, to be proactive in the way that I tend to be. Another key to better relationships is accepting that you are you and others are, well, them.
Once I started to voice my needs more, one of two things started to happen. Either people fell off or they stepped up. Both results were ultimately for my good. That's why, I am a huge encourager of individuals expressing their needs while asking the people in their life what they need from them in return. If the needs can be met, cool. If they can't, well, there's no time like the present to move out of the way so that someone else can—and will.
10. What Can I Do to Support You at this Stage in Your Life?
If all of us are truly taking our gifts, talents and time seriously, we're not in the same place nor are we the same person that we were this time last year. This means that some of our goals, desires and perhaps, even insights have shifted. This also means that what we needed this time last year may be different than what we require now. That is why I'm ending this piece with suggesting that you ask the close friends in your life about how you can support them in this stage and season.
Case in point. This time last year, I didn't have my latest godchild. Watching her mom, one of my dearest friends, transition from one child to two has been remarkable. It has also meant that I've needed to help her in ways that I never had to before.
When it comes to maintaining strong, healthy and thriving friendships, support is actually one of my favorite words. It means to hold up. It means to endure. It means to "withstand without giving way". Just by caring enough to ask the close friends in your life how you can support them, it will convey a level of love and care that is getting rarer by the day. Two people who support each other, in the ways that they need to be supported, are two people who can stand the test of time on the friendship tip.
Y'all, these are the 10 questions that have truly blessed my friendships. I hope they can do the same for you. Whether it's this month or the next, make the time to connect in this way. No matter how the conversation plays out, it'll be for your—and your friends'—ultimate good.
Want more stories like this? Sign up for our newsletter here and check out the related reads below:
This Is How To Apply Love Languages To Your Friendships
10 Signs You've Got A Close (TOXIC) Friend
According To Aristotle, We Need 'Utility', 'Pleasure' & 'Good' Friends
Allow These Things To Happen Before Calling Someone "Friend"
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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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Love Is The Muse: How Skylar And Temi Built A Creative Life Together
When Temitope Ibisanmi DM’d the word “muse” to Skylar Marshai, he knew he was shooting his romantic shot. He didn’t realize, however, that he was connecting with his future business and creative partner, too.
“I was the boyfriend,” Temi says. “Everybody out there knows, you’re the cameraman at that point.”
Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Today, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak