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:
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Feature image by Giphy
Amber Riley has the type of laugh that sticks with you long after the raspy, rhythmic sounds have ceased. It punctuates her sentences sometimes, whether she’s giving a chuckle to denote the serious nature of something she just said or throwing her head back in rip-roarious laughter after a joke. She laughs as if she understands the fragility of each minute. She chooses laughter often with the understanding that future joy is not guaranteed.
Credit: Ally Green
The sound of her laughter is rivaled only by her singing voice, an emblem of the past and the future resilience of Black women stretched over a few octaves. On Fox’s Glee, her character Mercedes Jones was portrayed, perhaps unfairly, as the vocal duel to Rachel Berry (Lea Michele), offering rough, full-throated belts behind her co-star’s smooth, pristine vocals. Riley’s always been more than the singer who could deliver a finishing note, though.
Portraying Effie White, she displayed the dynamic emotions of a song such as “And I'm Telling You I'm Not Going” in Dreamgirls on London’s West End without buckling under the historic weight of her predecessors. With her instrument, John Mayer’s “Gravity” became a religious experience, a belted hymnal full of growls and churchy riffs. In her voice, Nicole Scherzinger once said she heard “the power of God.”
Credit: Ally Green
Riley’s voice has been a staple throughout pop culture for nearly 15 years now. Her tone has become so distinguishable that most viewers of Fox’s The Masked Singer recognized the multihyphenate even before it was revealed that she was Harp, the competition-winning, gold-masked figure with an actual harp strapped to her back.
Still, it wasn’t until recently that Riley began to feel like she’d found her voice. This sounds unbelievable. But she’s not referring to the one she uses on stage. She’s referencing the voice that speaks to who she is at her core. “Therapy kind of gave me the training to speak my mind,” the 37-year-old says. “It’s not something we’re taught, especially as Black women. I got so comfortable in [doing so], and I really want other people, especially Black women, to get more comfortable in that space.”
“Therapy kind of gave me the training to speak my mind. It’s not something we’re taught, especially as Black women."
If you ask Riley’s manager, Myisha Brooks, she’ll tell you the foundation of who the multihyphenate is hasn’t changed much since she was a kid growing up in Compton. “She is who she is from when I met her back when she was singing in the front of the church to back when she landed major roles in film and TV,” Brooks says. Time has allowed Riley to grow more comfortable, giving fans a more intimate glimpse into her life, including her mental health journey and the ins and outs of show business.
The actress/singer has been in therapy since 2019, although she suffered from depression and anxiety way before that. In a recent interview with Jason Lee, she recalls having suicidal ideation as a kid. By the time she started seeing a psychologist and taking antidepressants in her thirties, her body had become jittery, a physical reminder of the trauma stacked high inside her. “I was shaking in [my therapist’s] office,” she tells xoNecole. “My fight or flight was on such a high level. I was constantly in survival mode. My heart was beating fast all the time. All I did was sweat.”
There wasn’t just childhood trauma to account for. After auditioning for American Idol and being turned away by producers, Riley began working for Ikea and nearly missed her Glee audition because her car broke down on the highway while en route. Thankfully, Riley had been cast to play Mercedes Jones. American Idol had temporarily convinced her she wasn’t cut out for the entertainment industry, but this was validation that she was right where she belonged. Glee launched in 2009 with the promise of becoming Riley’s big break.
In some ways, it was. The show introduced Riley to millions of fans and catapulted her into major Hollywood circles. But in other ways, it became a reminder of the types of roles Black women, especially those who are plus-sized, are relegated to. Behind the scenes, Riley says she fought for her character "to have a voice" but eventually realized her efforts were useless. "It finally got to a point where I was like, this is not my moment. I'm not who they're choosing, and this is just going to have to be a job for me for now," she says. "And, that's okay because it pays my bills, I still get to be on television, I'm doing more than any other Black plus-sized women that I'm seeing right now on screen."
The actress can recognize now that she was navigating issues associated with trauma and low self-esteem at the time. She now knows that she's long had anxiety and depression and can recognize the ways in which she was triggered by how the cult-like following of the show conflicted with her individual, isolated experiences behind the scenes. But she was in her early '20s back then. She didn't yet have the language or the tools to process how she was feeling.
Riley says she eventually sought out medical intervention. "When you're in Hollywood, and you go to a doctor, they give you pills," she says, sharing a part of her story that she'd never revealed publicly before now. "[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that's not fixing my problem. If anything, it's making it worse."
“[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that’s not fixing my problem. If anything it’s making it worse.”
Credit: Ally Green
At one point, while in her dressing room on set, she rested her arm on a curling iron without realizing it. It wasn't until her makeup artist alerted her that she even realized her skin was burning. Once she noticed, she says she was "so zonked out on pills" that she barely reacted. Speaking today, she holds up her arm and motions towards a scar that remains from the incident. She sought help for her reliance on the pills, but it would still be years before she finally attended therapy.
This stress was only compounded by the trauma of growing up in poverty and the realities of being a "contract worker." "Imagine going from literally one week having to borrow a car to get to set to the next week being on a private jet to New York City," she says. After Glee ended, so did the rides on private planes. The fury of opportunities she expected to follow her appearance on the show failed to materialize. She wasn't even 30 yet, and she was already forced to consider if she'd hit her career peak.
. . .
We’re only four minutes into our Zoom call before Riley delivers her new adage to me. “My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway,” she says.
On this Thursday afternoon in April, the LA-based entertainer is seated inside her closet/dressing room wearing a cerulean blue tank top with matching shorts and eating hot wings. This current phase of healing hinges on balance. It’s about having discipline and consistency, but not at the risk of inflexibility. She was planning to head to the gym, for instance, but she’s still tired from the “exhausting” day before. Instead, she’s spent her day receiving a massage, eating some chicken wings, and planning to spend quality time with friends. “I’m not going to beat myself up for it. I’m not going to talk down to myself. I’m going to eat my chicken wings, and then tomorrow I’m [back] in the gym,” she says.
“My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway."
This is the balance with which she's been approaching much of her life these days. It's why she's worried less about whether or not people see her as someone who is humble. She'd rather be respected. "I think you should be a person that's easy to work with, but in the moments where I have to ruffle feathers and make waves, I'm not shying away from that anymore. You can do it in love, you don't have to be nasty about it, but I had to finally be comfortable with the fact that setting boundaries around my life – in whatever aspect, whether that's personal or business – people are not going to like it. Some people are not going to have nice things to say about you, and you gotta be okay with it," she says.
When Amber talks about the constant humbling of Black women in Hollywood, I think of the entertainers before her who have suffered from this. The brilliant, consistent, overqualified Black women who have spoken of having to fight for opportunities and fair pay. Aretha Franklin. Viola Davis. Tracee Ellis Ross. There's a long list of stars whose success hasn't mirrored their experiences behind the scenes.
Credit: Ally Green
If Black women outside of Hollywood are struggling to decrease the pay gap, so, too, are their wealthier, more famous peers.
Riley says there’s been progress in recent years, but only in small ways and for a limited group of people. “This business is exhausting. The goalpost is constantly moving, and sometimes it’s unfair,” she says. But, I have to say it’s the love that keeps you going.”
“There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman,” she continues. “We’re still niche. We’re still not main characters.”
"There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman. We’re still niche. We’re still not main characters.”
Last year, Riley starred alongside Raven Goodwin in the Lifetime thriller Single Black Female (a modern, diversified take on 1992’s Single White Female). It was more than a leading role for the actress, it also served as proof that someone who looks like her can front a successful project without it hinging on her identity. It showcased that the characters she portrays don’t “have to be about being a big girl. It can just be a regular story.”
Riley sees her work in music as an extension of her efforts to push past the rigid stereotypes in entertainment. Take her appearance on The Masked Singer, for instance. Riley said she decided to perform Mayer’s “Gravity” after being told she couldn’t sing it years earlier. “I wanted to do ‘Gravity’ on Glee. [I] was told no, because that’s not a song that Mercedes would do,” she says. “That was a full circle moment for me, doing that on that show and to hear what it is they had to say.”
As Scherzinger praised the “anointed” performance, a masked Riley began to cry, her chest heaving as she stood on stage, her eyes shielded from view. “You have to understand, I have really big names – casting directors, producers, show creators – that constantly tell me ‘I’m such a big fan. Your talent is unmatched.’ Hire me, then,” she says, reflecting on the moment.
Recently, she’s been in the studio working on original music, the follow-up to her independently-released debut EP, 2020’s Riley. The sequel to songs such as the anthemic “Big Girl Energy” and the reflective ballad “A Moment” on Riley, this new project hones in on the singer’s R&B roots with sensual grooves such as the tentatively titled “All Night.” “You said I wasn’t shit, turns out that I’m the shit. Then you called me a bitch, turns out that I’m that bitch. You said no one would want me, well you should call your homies,” she sings on the tentatively titled “Lately,” a cut about reflecting on a past relationship. From the forthcoming project, xoNecole received five potential tracks. Fans likely already know the strengths and contours of Riley’s vocals, but these new songs are her strongest, most confident offerings as an artist.
“I am so much more comfortable as a writer, and I know who I am as an artist now. I’m evolving as a human being, in general, so I’m way more vulnerable in my music. I’m way more willing to talk about whatever is on my mind. I don’t stop myself from saying what it is I want to say,” she says.
Credit: Ally Green
“Every era and alliteration of Amber, the baseline is ‘Big Girl Energy.’ That’s the name of her company,” her manager Brooks says, referencing the imprint through which Riley releases her music after getting out of a label deal several years ago. “It’s just what she stands for. She’s not just talking about size, it’s in all things. Whether it’s putting your big girl pants on and having to face a boardroom full of executives or sell yourself in front of a casting agent. It’s her trying to achieve the things she wants to do in life.”
Riley says she has big dreams beyond releasing this new music, too. She’d love to star in a rom-com with Winston Duke. She hasn't starred in a biopic yet, but she’d revel in the opportunity to portray Rosetta Tharpe on screen. She’s determined that her previous setbacks won’t stop her from dreaming big.
“I think one of my superpowers is resilience because, at the end of the day, I’m going to kick, scream, cry, cuss, be mad and disappointed, but I’m going to get up and risk having to deal with it all again. It’s worth it for the happy moments,” she says.
If Riley seems more comfortable and confident professionally, it’s because of the work she’s been doing in her personal life.
She’d previously spoken to xoNecole about becoming engaged to a man she discovered in a post on the site, but she called things off last year. For Valentine’s Day, she revealed her new boyfriend publicly. “I decided to post him on Valentine’s Day, partially because I was in the dog house. I got in trouble with him,” she says, half-joking before turning serious. “The breakup was never going to stop me from finding love. Or at least trying. I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness, and you enjoy it and work through it.”
Credit: Ally Green
"I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness and you enjoy it and work through it.”
With her ex, Riley was pretty outspoken about her relationship, even appearing in content for Netflix with him. This time around is different. She’s not hiding her boyfriend of eight months, but she’s more protective of him, especially because he’s a father and isn’t interested in becoming a public figure.
She’s traveling more, too. It’s a deliberate effort on her part to enjoy her money and reject the trauma she’s developed after experiencing poverty in her childhood. “I live in constant fear of being broke. I don’t think you ever don’t remember that trauma or move past that. Now I travel and I’m like, listen, if it goes, it goes. I’m not saying [to] be reckless, but I deserve to enjoy my hard work.”
After everything she’s been through, she certainly deserves to finally let loose a bit. “I have to have a life to live,” she says. “I’ve got to have a life worth fighting for.”
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