When it comes to my semi-sordid-somewhat-random sexual past, something that I'm pretty open about is, I had a pattern of sleeping with my male friends. What was that all about? Well, to this day, I've never had a one-night stand before and, I wasn't very quick to have sex with people either. For me, I needed more than just a physical attraction or even chemistry; there needed to be a true emotional connection of some sort—and that tended to manifest via my male friendships. Now, for a guy and I to get to a point of "showing each other our parts", clearly we were never truly platonic (check out "The Word 'Platonic' Is Sacred. Literally.")—yet, at the same time, there was enough of an attraction to wonder what it would be like to "take it there".
To tell you the truth, I'm still trying to figure out if that mindset was crazy or not. At the time, my rationale was, "I like him and I trust him. I don't really want anything super serious right now so, sex with a friend seems like the best of both worlds: the buddy and the booty." (That last part is a line that Queen Latifah said in the movie Brown Sugar). But when I tell you that sex, even so-called casual sex (also check out "We Should Really Rethink The Term 'Casual Sex'"), changes the dynamic of a relationship—any kind of relationship—it is so true. Sometimes, it alters it in ways that you wouldn't quite expect. Take if you engage in sex with a friend, believing that it will be all good and then, when it's all said and done, it's bad. Shoot, worse than that.
Even if you both went in, not expecting to pledge your undying love for each other, less-than-stellar sex can still bruise egos and make things hella awkward (I'm saying that from personal experience). So, if it ever happens to happen to you, what can you do to preserve your friendship? These five questions can hopefully help to bring you some peace and your relationship, moving forward, with some clarity.
What Made It “Bad”?
Bad sex. If you're on this planet long enough (and you are sexually active while living on it), you'll experience some at some point. Thing is, the reasons can run the gamut. You may lack sexual compatibility. Someone may not be as "sexually knowledgeable" as they let on to be. What you fantasized in your mind may not be even close to the reality. Maybe your partner is selfish, boring or both. Like I said, the possibilities are pretty endless. But knowing what made the sex not so impressive is what can help you to figure out how to proceed.
Take one male friend who I had sex with. I always refer to him as my Cirque du Soleil-in-under-15-minutes experience because, I don't know what the brotha was trying to prove, but it was like he was trying to do everything possible in the time it takes to watch half of a sitcom. Before the sex, while I wasn't interested in being in a romantic relationship with him, I did find him to be fine as hell; so, I wanted to see if he was as good in bed as he looked (hey, I'm just being honest). He. Absolutely. Was. Not. Purely on the physical tip, the sex was so wack that it was almost comical. It was so bad, in fact, that there was no reason for us to fall out or anything. In fact, in hindsight, the end result is we became just friends. It was even hard to see him as fine anymore.
But if it had been bad because he mistreated me, lied about some other situations he had going on, gave me an STD, etc., etc.—well, I could see how that could produce an entirely different outcome. So yeah, if you are trying to figure out how to recover from a bad sex session with a friend, getting down to what made it so horrible in the first place is the first thing that I'd advise you to do. That, right there, can reveal…a lot.
What Was Your Motive for Doing It in the First Place?
An author by the name of Paul David Tripp once said, "We rarely do anything with one single motive." That really is so true. A motive is what causes us to act a certain way or it's the goal that we set to attain by saying or doing certain things. Keeping this in mind, a person's motive (or set of motives) tends to reveal quite a bit about them. That said, when you decided to sleep with your friend, what caused you to do it? What end game did you have in mind? If it all boiled down to curiosity, horniness or simply trying to "scratch and itch", for the most part, those reasons are pretty superficial and, like a surface cut or wound, you can "heal" from that pretty quickly. In time, the two of you might even be able to laugh about it (maybe). But if it even remotely had to do with some of the stuff that I said in the article "When He Just Wants To Be Friends, But You Want More...", that is another matter entirely.
One of the biggest gambles that comes with having sex with a friend, even if it is just so-called casual sex, is it still has the tendency to connect you to your partner on another level (after all, oxytocin doesn't know if you like, love or are in love with who you sleep with).
So, if you weren't honest with yourself before engaging with your friend, you could be lying to both of you about what your core motive was. On top of that, what made sex bad for you could be about more than just the physical. Maybe you were hoping it would start off casual but end up with him seeing you in another light. Or, maybe you thought that you would put it on him and it could become a steady thing, while he had more of a one-and-done mentality about everything. Yeah, a lot of us end up with our feelings hurt or being the peak of pissed because we weren't forthcoming about why we set out to do something. If you are "feeling some type of way" about the sex that you and your homie had, get back to the foundation before doing anything else. Ponder what your true motive was for taking things there.
Does He Feel the Same Way That You Do?
For this particular topic, I decided to hit up a good friend of mine in order to get the male perspective, since I happen to know that he's had quite a bit of experience when it comes to sleeping with female friends. As we were discussing a message I once heard about the fact that women deal in "wire" or string (everything tends to connect to everything else) while men deal in "boxes" (they tend to compartmentalize stuff), he shared with me that this fact actually applies to this scenario.
"When it comes to us, sex has to be really bad for it to totally suck. Like, for me, I would say that if it would be easier for me to get a nut by jacking off than having sex with someone…yeah, that means she's bad in bed. Otherwise, even if the sex isn't great, I probably won't even bring up that my mind wasn't blown. For me, it's more about if you are bringing drama to the friendship outside of the sex. Can I still talk to you about other women? Are you about to have unrealistic expectations? Are you trying to be more than friends on the sly? If we can still maintain our friendship, I'll be real with you—we can still be friends and probably have sex because guys don't look at sex as being 'good' or 'bad' so much as who is better or best."
Interesting. I asked a few other fellas I know to share their thoughts on this, and they basically nodded their heads in agreement. To me, what this all boils down to is, unless your male friend has been secretly crushin' on you, chances are, you don't have to worry about unimpressive casual sex with him ruining anything. That is, unless you choose for it to.
If It Was Truly “Casual”, What’s the Problem?
I'm pretty word particular. That's why, personally, I'm not a fan of the word "casual" being used in the context of relationships. Casual means without serious intention. Casual means careless. Casual means apathetic and unconcerned. Seems kind of weird that two friends—two true friends—would intentionally participate together in anything that falls in line with those definitions. But if you have, again, I get it. Because I didn't think all of this through super deeply at the time, I've been there.
And you know what? A part of what caused casual sex to ruffle some feathers in my friendly hook-ups is that I expected the sex to be casual but not the "aftercare" that followed. Meanwhile, my male friends were like, "If we're having sex with serious intention, why should I be penalized for not being super concerned if you didn't enjoy it as much as you expected to or if I'm exactly the same afterwards? We just friends, so what's with all of the 'extra'?" And, to a large degree, those guys would have a point.
If the two of you had sex one night and had some really bad sex, all with the understanding that it shouldn't have happened and neither of you want it to happen again, there really shouldn't be (too) much more energy put into it. But if something about the definitions of casual trigger you, when it comes to what went down between you and your friend, well, something tells me that it might not be as casual as you've been trying to let on. Something tells me that, even if you don't have serious feelings for your friend, you are looking for a little more interest and empathy on his part. And, if that is indeed the case…you should probably ask yourself "why?".
Do You (Still) Value the Friendship More than Anything Else?
Out of everything that we discussed in this, at the end of the day, what it all boils down to is what you value the most—holding onto a disappointing sexual experience or preserving your friendship. Now, if something about the sexual experience has caused you to question your value or self-worth, please get down to the root of that as soon as possible. No matter how unimpressive a sexual experience is, if it's with a friend, it still shouldn't affect or infect you in that way. But if it really just boils down to the bad sex making things weird and awkward, remember that this is your friend that we're talking about. Like my male friend said, chances are, it's eating at you far more than it is your male friend. Plus, he probably wants to get past it all so that you can get back to being just friends.
The main thing to keep in mind is that sex with a friend, whether it's good or bad sex, tends to alter things more times than not. And, many times, how it does that is unpredictable. If you're not prepared to deal with those odds, you might want to stay out of the bedroom. After all, there are so many other options out here. Why take this kind of risk with your male friend(s)? For real.
Want more stories like this? Sign up for our newsletter here and check out the related reads below:
Who Knew There Was Such A Thing As "Bad Orgasms"?
When Your Sex Drives Aren't in Sync
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Feature image by Giphy
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It Girl 100 became xoNecole’s most successful program, with the hashtag organically reaching more than forty million impressions on Instagram in just twenty-four hours. Yes, it caught on like wildfire because we celebrated some of the most brilliant and influential GenZennial women of color setting trends and shaping culture. But more than that, it resonated because the women we celebrated felt seen.
Many were already known in their industries for keeping this generation fly and lit, but rarely received recognition or flowers. It Girl 100 became a safe space to be uplifted, and for us as Black women to bask in what felt like an era of our brilliance, beauty, and boundless influence on full display.
And then, almost overnight, it was as if the rug was pulled from under us as Black women, as the It Girls of the world.
Our much-needed, much-deserved season of ease and soft living quickly metamorphosed into a time of self-preservation and survival. Our motion and economic progression seemed strategically slowed, our light under siege.
The air feels heavier now. The headlines colder. Our Black girl magic is being picked apart and politicized for simply existing.
With that climate shift, as we prepare to launch our second annual It Girl 100 honoree list, our team has had to dig deep on the purpose and intention behind this year’s list. Knowing the spirit of It Girl 100 is about motion, sauce, strides, and progression, how do we celebrate amid uncertainty and collective grief when the juice feels like it is being squeezed out of us?
As we wrestled with that question, we were reminded that this tension isn’t new. Black women have always had to find joy in the midst of struggle, to create light even in the darkest corners. We have carried the weight of scrutiny for generations, expected to be strong, to serve, to smile through the sting. But this moment feels different. It feels deeply personal.
We are living at the intersection of liberation and backlash. We are learning to take off our capes, to say no when we are tired, to embrace softness without apology.
And somehow, the world has found new ways to punish us for it.
In lifestyle, women like Kayla Nicole and Ayesha Curry have been ridiculed for daring to choose themselves. Tracee Ellis Ross was labeled bitter for speaking her truth about love. Meghan Markle, still, cannot breathe without critique.
In politics, Kamala Harris, Letitia James, and Jasmine Crockett are dragged through the mud for standing tall in rooms not built for them.
In sports, Angel Reese, Coco Gauff, and Taylor Townsend have been reminded that even excellence will not shield you from racism or judgment.
In business, visionaries like Diarrha N’Diaye-Mbaye and Melissa Butler are fighting to keep their dreams alive in an economy that too often forgets us first.
Even our icons, Beyoncé, Serena, and SZA, have faced criticism simply for evolving beyond the boxes society tried to keep them in.
From everyday women to cultural phenoms, the pattern is the same. Our light is being tested.
And yet, somehow, through it all, we are still showing up as that girl, and that deserves to be celebrated.
Because while the world debates our worth, we keep raising our value. And that proof is all around us.
This year alone, Naomi Osaka returned from motherhood and mental health challenges to reach the semifinals of the US Open. A’ja Wilson claimed another MVP, reminding us that beauty and dominance can coexist. Brandy and Monica are snatching our edges on tour. Kahlana Barfield Brown sold out her new line in the face of a retailer that had been canceled. And Melissa Butler’s company, The Lip Bar, is projecting a forty percent surge in sales.
We are no longer defining strength by how much pain we can endure. We are defining it by the unbreakable light we continue to radiate.
We are the women walking our daily steps and also continuing to run solid businesses. We are growing in love, taking solo trips, laughing until it hurts, raising babies and ideas, drinking our green juice, and praying our peace back into existence.
We are rediscovering the joy of rest and realizing that softness is not weakness, it is strategy.
And through it all, we continue to lift one another. Emma Grede is creating seats at the table. Valeisha Butterfield has started a fund for jobless Black women. Arian Simone is leading in media with fearless conviction. We are pouring into each other in ways the world rarely sees but always feels.
So yes, we are in the midst of societal warfare. Yes, we are being tested. Yes, we are facing economic strain, political targeting, and public scrutiny. But even war cannot dim a light that is divinely ours.
And we are still shining.
And we are still softening.
And we are still creating.
And we are still It.
That is the quiet magic of Black womanhood, our ability to hold both truth and triumph in the same breath, to say yes, and to life’s contradictions.
It is no coincidence that this year, as SheaMoisture embraces the message “Yes, And,” they stand beside us as partners in celebrating this class of It Girls. Because that phrase, those two simple words, capture the very essence of this moment.
Yes, we are tired. And we are still rising.
Yes, we are questioned. And we are the answer.
Yes, we are bruised. And we are still beautiful.
This year’s It Girl 100 is more than a list. It is a love letter to every Black woman who dares to live out loud in a world that would rather she whisper. This year’s class is living proof of “Yes, And,” women who are finding ways to thrive and to heal, to build and to rest, to lead and to love, all at once.
It is proof that our joy is not naive, our success not accidental. It is the reminder that our light has never needed permission.
So without further ado, we celebrate the It Girl 100 Class of 2025–2026.
We celebrate the millions of us who keep doing it with grace, grit, and glory.
Because despite it all, we still shine.
Because we are still her.
Because we are still IT, girl.
Meet all 100 women shaping culture in the It Girl 100 Class of 2025. View the complete list of honorees here.
Featured image by xoStaff
Then there were those who gave up their zip code altogether and found a permanent home in the skies. After years spent recruiting students for a university, Lisa-Gaye Shakespeare became a full-time travel influencer and founded her travel company, Shakespeare Agency. And she's not alone.
These stories mirror the experiences of women across the world. For millions, the pandemic induced a seismic shift in priorities and desires. Corporate careers that were once hailed as the ultimate “I made it” moment in one's career were pushed to the back burner as women quit their jobs in search of a more self-fulfilling purpose.
xoNecole spoke to these three Black women who used the pandemic as a springboard to make their wildest dreams a reality, the lessons they learned, and posed the question of whether they’ll ever return to cubicle life.
Answers have been edited for context and length.
xoNecole: How did the pandemic lead to you leaving the cubicle?
Randi: I was becoming stagnant. I was working in mortgage and banking but I felt like my personality was too big for that job! From there, I transitioned to radio but was laid off during the pandemic. That’s what made me go full throttle with entrepreneurship.
Gabrielle: I moved around a lot for work. Five times over a span of seven years. I knew I needed a break because I had experienced so much. So, I just quit one day. Effective immediately. I didn’t know what I was going to do, I just knew I needed a break and to just regroup.
Lisa-Gaye: I was working in recruiting at a university and my dream job just kind of fell into my lap! But, I never got to fully enjoy it before the world shut down in March [2020] and I was laid off. On top of that, I was stuck in Miami because Jamaica had closed its borders due to the pandemic before I was able to return.
Randi O
xoN: Tell us about your journey after leaving Corporate America.
Randi: I do it all now! I have a podcast, I’m an on-air talent, I act, and I own a public relations company that focuses on social media engagement. It’s all from my network. When you go out and start a business, you can’t just say, “Okay I’m done with Corporate America,” and “Let me do my own thing.” If you don’t build community, if you don’t build a network it's going to be very hard to sustain.
Gabrielle: I realized in New York, there was not a lot to do for Black lesbians and queer folks. We don’t really have dedicated bars and spaces so I started doing events and it took off. I started focusing on my brand, Raw Honey. I opened a co-working space, and I was able to host an NYC Pride event in front of 100,000 people. I hit the ground running with Raw Honey. My events were all women coming to find community and come together with other lesbians and queer folks. I found my purpose in that.
Lisa-Gaye: After being laid off, I wrote out all of my passions and that’s how I came up with [my company] Shakespeare Agency. It was all of the things that I loved to do under one umbrella. The pandemic pulled that out of me. I had a very large social media following, so I pitched to hotels that I would feature them on my blog and social media. This reignited my passion for travel. I took the rest of the year to refocus my brand to focus solely on being a content creator within the travel space.
Gabrielle
xoN: What have you learned about yourself during your time as an entrepreneur?
Randi: [I learned] the importance of my network and community that I created. When I was laid off I was still keeping those relationships with people that I used to work with. So it was easy for me to transition into social media management and I didn’t have to start from scratch.
Gabrielle: The biggest thing I learned about myself was my own personal identity as a Black lesbian and how much I had assimilated into straight and corporate culture and not being myself. Now, I feel comfortable and confident being my authentic self. Now, I'm not sacrificing anything else for my career. I have a full life. I have friends. I have a social life. And when you are happy and have a full quality of life, I feel like [I] can have more longevity in my career.
Lisa-Gaye: [I'm doing] the best that I've ever done. The discipline that I’m building within myself. Nobody is saying, ‘Oh you have to be at work at this time.’ There’s no boss saying, ‘Why are you late?’ But, if I’m laying in bed at 10 a.m. then it's me saying [to myself], 'Okay, Lisa, get up, it's time for you to start working!’ That’s all on me.
xoNecole: What mistakes do you want to help people avoid when leaving Corporate America?
Randi: You have to learn about the highs and lows of entrepreneurship. You have a fast season and a slow season and I started to learn that when you're self-employed the latter season hits hard. Don't get caught up on the lows, just keep going and don't stop. I’m glad I did.
Gabrielle: I think everyone should quit their job and just figure it out for a second. You will discover so much about yourself when you take a second to just focus on you. Your skill set will always be there. You can’t be afraid of what will happen when you bet on yourself.
Lisa-Gaye: When it comes to being an influencer the field is saturated and a lot of people suffer from imposter syndrome. There is nothing wrong with being an imposter but find out how to make it yours, how to make it better. If you go to the store, you see 10 million different brands of bread! But you are choosing the brand that you like because you like that particular flavor.
So be an imposter, but be the best imposter of yourself and add your own flair, your own flavor. Make the better bread. The bread that you want.
Lisa-Gaye Shakespeare
xoNecole: Will you ever return to your 9 to 5?
Randi: I wouldn’t go back to Corporate America. But I don’t mind working under someone. A lot of people try to get into this business saying, “I can't work under anyone.” That’s not necessarily the reason to start a business because you're always going to answer to somebody. Clients, brands, there’s always someone else involved.
Gabrielle: I went back! I really needed a break and I gave myself that. But, I realized I’m a corporate girl, [and] I enjoy the work that I do. I’m good at it and I really missed that side of myself. I have different sides of me and my whole identity is not Raw Honey or my queerness. A big side of me is business and that’s why I love having my career. Now I feel like my best self.
Lisa-Gaye: I really don’t. For right now, I love working for myself. It's gratifying, it's challenging, it's exciting. It’s a big deal for me to say I own my own business. That I am my own boss, and I'm a Black woman doing it.
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Featured image courtesy of Lisa-Gaye Shakespeare
Originally published on February 6, 2023