Insecure is the show that just keeps on giving, and no matter how long ago the show ended, we still talk about the friendships, relationships, and unforgettable moments that occurred on the show. One of the recurring conversations is who Issa Rae’s character, Issa Dee, should have really ended up. All the Insecure fans know that the men on the show were FIONE, and Issa had quite the roster. From Lawrence to Nathan, and who can forget Daniel? The men had our eyes glued to our TVs as well as the drama that came along with dating them chile.
However, have you ever wondered if the real people dated like their characters? Issa revealed whether or not they were dateable in real life during her sitdown with Cosmopolitan’s YouTube series Cheap Shots. Starting at the 9:21 mark, the actress and producer who recently released her very own Prosecco brand Viarae, ranked co-stars Jay Ellis (Lawrence), Y’lan Noel (Daniel), and Kendrick Sampson (Nathan) from most to least datable.
“Now, I could go the easy route and say, Jay, he’s married, so he’s technically the least dateable,” she explains. “The second least dateable is for sure Kendrick Sampson because, out of his mouth, he does not like to date,” she reveals. “He’s not a player, but he’s just a lot.”
So, that leaves Y’lan in the number one spot, which I’m sure sounds like music to the ears of Daniel fans everywhere. But not so fast. “And then Y’lan, I think he’s probably the most dateable, but even he’s like…just don’t date actors. All actors are trash, honestly.”
Oh, Issa! While most of the actors keep their personal lives private, there is some information available about their romantic pasts. Here’s what we know.
Y’lan Noel
Y'lan Noel
Photo by Amanda Edwards/Getty Images
The Photograph actor actually dated a certain Insecure co-star. Last December, Amanda Seales revealed on her podcast, The Amanda Show, that she and Y’lan used to be a thing. She even recalled a time when he made her birthday a special moment she wouldn't forget. Let's just say it involves a romantic boat ride, dolphins, a live art performance, and a picnic.
Kendrick Sampson
Kendrick’s dating life has been pretty nonexistent except for a few rumors here and there. The Miss Juneteenthactor was rumored to be dating Naomi Campbell after they both graced the March 2019 cover of British Vogue.
Jay Ellis
Jay Ellis
Photo by Amy Sussman/Getty Images
Jay is officially off the market after tying the knot in 2022 to longtime partner Nina Senicar. They share a daughter together. Prior to Nina, he also dated The Game actress Brittany Daniel.
Issa Rae Takes Cheap Shots at THESE Celeb Alcohol Brands | Cheap Shots | Cosmopolitan
Issa Rae showed up to Cosmo the morning after a fun night out, and we decided to keep the party going as we presented the writer and actress trays of cheap a...Let’s make things inbox official! Sign up for the xoNecole newsletter for daily love, wellness, career, and exclusive content delivered straight to your inbox.
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Taja, an actress known most for her role on BET’s The Oval, and businessman/model Ryan Easter tied the knot on July 27 in an intimate and beautiful wedding in LA - surrounded by friends and family. During our 40+ minute conversation, the newlyweds opened up about the inner work journey they both went through individually to become their best selves.
Taja revealed that her grateful and light spirit came after being in a depressive state and doing a great deal of healing and education. And Ryan shared how losing a parent as a youth affected how he showed up in the world and the truths he had to face to embrace who he is wholly.
The pair also chatted about the power of intention, the importance of working through trauma, and the work they do every day to honor their partnership. There’s a reason their glow is so beautiful! It comes from the inside.
“You're meeting me now after I've done all this work, but I had to go through it to get to that space and be in a very happy, healed relationship,” Taja says. Check out the layered conversation below.
xoNecole: I’ll start with the most obvious question: how did you two meet, and what were your initial feelings about each other?
Ryan Easter: We connected through friends. At the time, I was in New York, and she was back and forth between LA and Atlanta. But our mutual female friends were together and decided they needed to set me up. So they confirmed I was looking for something serious and then sent me her picture.
And I was like, "Okay, she looks good - a chocolate drop." But then I thought, "What's wrong with her? So, I called them up, and one of them was messing with me and said, "Oh, she's a little crazy." I was like, "Whoa, I can't do crazy anymore. I've dealt with that before. I’d rather stay by myself than deal with that again." Then she clarified, "No, I'm just kidding. She's crazy in a good way. She's a lot of fun and has her stuff together. That’s how it started for me.
Taja Simpson: I was just going about my life, getting ready for another season of The Oval, when I got a text from my friend Natasha. She said, "Hey, I don't think you're dating anybody, but I have a friend I think you should meet. He's a great guy." She gave me this huge pedigree, saying they had been friends for 19 years. I thought, "Wow, he sounds amazing." But when she sent me a photo, I didn’t like it.
Later, I thought about it and figured it could just not be a good picture. So she sent his Instagram which had all these modeling fitness pictures and stuff. And then I was like, wow - you had my whole husband this time and didn’t tell me - now I told her she could give him my number.
"I was just going about my life, getting ready for another season of The Oval, when I got a text from my friend Natasha. She said, "Hey, I don't think you're dating anybody, but I have a friend I think you should meet. He's a great guy." She gave me this huge pedigree, saying they had been friends for 19 years. I thought, "Wow, he sounds amazing." But when she sent me a photo, I didn’t like it."
Taja Simpson & Ryan Easter
Photo by @jorgemezaphotos
xoN: I love that because, you know, there's all these conversations about the ways people meet, and I still feel like friends and family are one of the best ways. It’s like they know you! What are your thoughts?
Ryan: Yeah, absolutely! You feel a great sense of obligation to be the best version of yourself because you’re not just representing yourself; you’re also representing the person who referred you. I can’t go out there acting like a fool and have them looking at their friend like, "Why did you hook me up with this clown?" It’s like, we're gonna be clear and honest about our intentions. And if it works, great, and if it doesn't, it's okay.
Taja: Exactly. When he called, we spoke that day for like, an hour. The rest was history. We just connected, and it was great. After that, we started talking every day, and now here we are.
xoN: Okay, so tell me about your first date! Do you remember where you went? What did you do? How was the vibe?
Taja: Our first in-person date was two months after we met over the phone. This was during COVID, so we got introduced in July 2020 but didn’t meet until September. From July to September, we were doing video dates and phone calls, building up this excitement about meeting in person. I was really nervous. I thought, "Oh my God, is it going to be like it was over the phone?" We really connected and vibed. I was there to pick him up at LAX, and I felt like this was it. I thought, "God put this brother in my life to be this good, this perfect." It felt too good to be true.
I actually had a friend meet us at the airport to film our meeting without him knowing. I told her to stay in the corner and keep the camera hidden. When he was coming down the escalator, I had this whole plan to run up to him in slow motion and jump into his arms. When I saw him, I froze. I was so nervous that I couldn’t move! He came up to me, gave me a big hug, and swung me around, and I just thought, "Wow!" Everything I planned went out the window.
Ryan: I was really excited to meet her, too. Technically, our first date was at Firestone Brewery. After the airport, we went back to her place to drop off my stuff, and then she said, "I like to drink beer," so she took me to a brewery nearby.
I remember being there, and we were kind of embracing, but not too much since it was technically the first time we were in physical proximity. You still have to play it cool, even after talking for a while. But every time I touched her, it felt good. I thought, "Yeah, this is it." When we hugged at the airport, I felt like, "Yo, this is home." At that moment, I knew she was the one.
xoN: Ugh, I love that. So when did the courtship start to develop into a relationship? Did y'all have that conversation?
Ryan: Initially, we were very clear about our intentions. We were both dating with purpose and had similar aspirations of eventually finding someone to marry, start a family, create businesses together, and live our lives to the fullest. We knew from the beginning that this was our goal and checked in with each other to see if we were on the same page.
After establishing our intentions, it was about having those small conversations. We discussed what was important to each of us—our needs, wants, likes, dislikes, triggers, and traumas. All those details are crucial for building a solid foundation for a healthy relationship. We spent a lot of time getting to know the real person, not just the representative we might present to the world.
Sometimes, it’s difficult because it requires us to be extremely vulnerable. For men, especially in our society, vulnerability is often frowned upon, making it hard to expose that sensitive side. You never know how people will react—some might use it against you, while others might protect you.
I think for her; it took her understanding that mentality that men have and use that to her advantage to make sure she's like, look, this is a safe space for you to allow me to see the full person that you are. I appreciated that because, like, I would tell her, if you really want a man to value you, he has to feel safe with you, right, not necessarily in a physical capacity but more so from an emotional standpoint; I need to feel like I can be safe with you emotionally.
So that courtship was a lot of just having those serious, sometimes difficult conversations about things we're going through in the past to things we aspire to accomplish in the future, to things that we're currently dealing with, and started to gain that understanding about who we are and what we aspire to be, and just continue to flow.
"So that courtship was a lot of just having those serious, sometimes difficult conversations about things we're going through in the past to things we aspire to accomplish in the future, to things that we're currently dealing with, and started to gain that understanding about who we are and what we aspire to be, and just continue to flow."
Taja: I mean, that's exactly right, and a lot of it we spoke about even before we met. Because it was this free thing where we didn’t know each other. We didn't have to be a representative. I was just my authentic self. It’s like - I'm an actor, and I got five or six characters that may come out in our conversation. I'll be funny, then the next moment, I'll be serious. It just happens.
I was very vocal about how I foresee my life going. Also, because I'm in entertainment, that played a part. I had met people before who couldn't handle that. They wanted a woman with a nine-to-five, a teacher, or just somebody with a very strict schedule. But that wasn't me. So I think we were super intentional when it came to dating and making sure we can build and grow together. So, we made that commitment prior to him leaving. He came to LA for a week, and the day before he left, it was like, okay, so this is it.
xoN: I’ve noticed that intention and vulnerability are both powerful words that you two keep using, which I think is essential for any long-term relationship. What are some of your other shared values?
Ryan: Also, we both understood the power of mindset. When you see successful or unsuccessful people, sometimes others will attribute their state to their family or money. And I'm not saying that that doesn't help. But there are a lot of people who have come from very humble beginnings and very troubled past that have gone on to do great things, and it all had to do with their mindset. They had to leave and see themselves doing what they desired to do before it became a reality in the physical realm.
I think a lot of those beliefs and mentalities that we shared was refreshing because, you know, we've all known people that every time you talk to them, something bad is going on. And it's such a drag because they can bring your energy down. We don't subscribe to that. Not saying that we don't go through tough times. But when we do, the question that we always ask ourselves is, what is it that I'm supposed to learn from this? I think those type of elements of just being in alignment mentally about how we view the world definitely help to solidify our relationship and our connection.
Taja: When we met, I was in a headspace of growth. We now call it believe, evolve, become because you have to believe that thing right in order to show up. We both understand that your vibration precedes your manifestation, so you have to vibrate and believe at a certain level. Act as if you have to be in that space, that energy, in order for that thing to come so you can evolve and then become whatever that said thing is. But I was in that headspace before we met, and I was clearing out people in my life.
I was really intentional with finding someone that was in that headspace, too. I was not okay with anyone being stagnant.
Taja Simpson & Ryan Easter
Photo by @jorgemezaphotos
xoN: You two seem so evolved individually and collectively. I'm curious, were there any challenges that you two had to get through together, and what did you learn from that experience?
Ryan: Being parents. And if your partner doesn't have a great pregnancy, then it can be tough, and it stretches you in a lot of ways. But I would definitely say the first five months of being new parents was a lot because we were both exhausted. And she's also trying to heal her body because giving birth puts a tremendous amount of stress on the woman's body. It gives you a different respect for the strength of femininity because I wouldn't want to go through that. And I was there the whole 29 hours.
So during that time I'm getting snappy because I need to rest. I have not been able to rest, and I'm sleep-deprived, and I don't feel like I got my foot in yet. And, and then, on top of that, you have this, this really small human that's completely dependent upon you. They can't do anything for himself, and that, even psychologically, that's a lot to carry. But the thing that I think that has helped us is that we understand that we won't always be on the same page. It's okay to have disagreements, but you always have to lead with love, meaning that if I'm upset with her or she's upset with me, we focus on what the issue is.
Taja: I had a horrible pregnancy and was still feeling like I want to be productive; it’s just part of who I am. And during the newborn phase, like he said, we were exhausted. We were zombies. I'm getting whiny. I need sleep. He's getting snappy and short, and we're having to figure out us. The hardest thing is trying to still learn how to effectively communicate in the midst of this space where you are exhausted; you don't feel good, nothing's going your way.
But I'm a big believer of being accountable, especially for women, because women are not always accountable. But we encourage each other to address the trauma and encourage positive self-thought and talk. Because what you think, speak, and do creates power for better and worse.
xoN: Were there any past traumas you had to heal from in order to love each other correctly, and do you feel comfortable discussing them?
Ryan: For me, the biggest thing was my father’s death at nine. You’re young, and you don’t know how to process the loss. It’s one of those things I thought I dealt with, but when I got into my adult years, I realized it didn’t. I always felt like I had to go above and beyond because I didn’t have my father there to be a man - I excelled in sports and academics, but it was based on an inadequate feeling.
I understand the importance of fathers in children’s life but you still have the power to be the best version of yourself whether your father is there or not. And I believe the almighty Creator will put people in your life to be the best version of yourself. I wanted to be that confident person for her and our children - and I didn’t want to carry that trauma into our relationship or our son. So I worked on it before us and I continue to now.
Taja: Mine was colorism. I grew up where the brown paper bag thing was a thing. There were kids I couldn’t play with because “I was too Black.” I had a family member who called me “Ew.” Like she’d literally say, come here, Ew, you ugly thing. And my family, for a long time, didn’t realize how it was breaking me. But eventually, my mom noticed and taught me more about self-esteem and then I started to do the work. But it still shows its head. I still would have thoughts that I’m not good enough because of how I look. I’ve literally not tried out for roles because of that. One of my friends’ friends has literally called out once that I was the only dark person at an event.
So when I started doing the work, I noticed the ways it showed up, like I just wouldn’t want to be in the sun long. I mean when I was younger, I used to pray to God to make me “better” or lighter. It took a long time to really get over that. There’s a book I wrote called Women Who Shine - where I got my thoughts out about this.
So he knows my sensitive spots and speaks to the little girl in me. It's so interesting how the things we go through when we’re young affect us in adulthood. Mental health is as important as physical health - and I’m grateful that he understands the importance of both of those.
xoN: Thank you for your vulnerability. I hope it helps someone else. Finally, I’ll close with this: what’s your favorite thing about each other?
Ryan: Definitely her mindset. She doesn’t have a victim mindset; she’s empowered. That’s so attractive. I believe that she prides herself on being a good, great communicator. She moves with integrity, you know, I think that's important. And you know, she also understands the importance of taking care of her physical, emotional, and mental wellbeing.
Taja: There’s so many. Where do I start? My husband is supremely supportive. I absolutely love that about him. Also, I love his intention. I love how effectively he communicates. I love how he fathers our child. I love how he looks. Because, praise God. Okay, I'm just gonna put that out there.
But you know what, my favorite thing about him is that I love that he's a man of integrity.
Integrity was the highest things on my list when I’d write out what I wanted in a partner. Because it’s everything. And so I love that I feel the level of safety that I feel with him, that I can completely be my 100% authentic self. I know that he's taking care of me, my heart, and our family. We're good.
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Feature image by @jorgemezaphotos
