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I'm Dating My Ex's Best Friend - And She's Trans Too | LOVE DON'T JUDGE
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Sep 7, 2025
WHEN Jesse and Elena first met, they were with their exes, and so were only platonic friends for a year. However, once they split from their respective partners, the relationship quickly blossomed into a romantic one. Since the beginning, their love has been marred in controversy, as Elena is a transgender woman, and Jesse is a straight man who is now in his second relationship with a trans girl. Jesse said, "Yes, she originally was a man. We all know that, but truly in her heart, she is a woman. So, therefore, I feel I am straight." He continued, "I've never seen a photo of Elena before she transitioned." Elena spoke about her journey, "I have medically transitioned. When it comes to terms with my breast augmentation and my facial feminization, as for SRS, which is s** reassignment surgery, I have not, mainly because I'm proud of being a transgender woman and I wouldn't change what I was created for." Online, the couple has received a lot of trolling. Jesse explained, "People online call me gay because I've been in relationships with two trans women." Commenters have said that Elena is "a man, still a man," "a man cosplaying as a woman", and the pair are "two dudes hanging out."
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0:00
I'm dating my ex's best friend and she's transgender too
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Yes, she originally was a man, but truly in her heart, she is a woman
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So therefore I am straight. I have medically transitioned. As for me and Simon's surgery, I have not
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People online call me gay because I've been in relationships with two trans women
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She's got a glizzy, he's gay. Two dudes hanging out. You are a man cosplaying as a woman
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This last two years of dating a trans woman, It's been very rough, I've lost a lot
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It's the hardest thing I've ever been through. She's a real Barbie, right
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We need her makeup to look good in the gym all the time. She's a real life Barbie right here
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I love her, and this is now my fiance. She's trans, I love putting it out there
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We don't do gender norms, and what we mean by that is what? I don't know
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I don't know what you mean. Gender norms. Yeah, and what about it
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We've been together for a year. Elena and I have met in Miami as friends
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to a bunch of other trans women, and we were friends for a year. We became an official couple four days after he became single
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People online call me gay because I've been in relationships with two trans women. Let me see that bubble
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You're not sweating. You're not doing it right. We're not done, baby. Let's go. We want that summer butt
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Elena helped me build myself and build my character, and she helped me realize what it is that I like in the bedroom
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Cut. Get my butt a smack. My wife loves grabbing my butt, so I've got to have that booty, too
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You feel me? Let's go. Perfect. Perfect. Go down more. We both met up at a time when we were both broken
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This lady got me sober. She got me clean. The only reason I'm alive is honestly because of her
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We're in the happiest place we've ever been. Two. Let's go. Three. Let's go
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Sacrifice is paradise. If you're not taking care of yourselves, then you're not taking care of your relationship
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Everybody in my life gave up on me at one time. And what did you do for me? I stuck beside you
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When I have what? Nothing. Nothing. We're gonna be the ones to show everyone
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what a couple like us is all about. I love you. All right, let's get out of here
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My transition journey has been rough. I've been on my own since I was 14
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So finding out who I was took a little time. I have medically transitioned when it comes to terms
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with my breast augmentation and my facial feminization As for SRS which is Reed and Simon surgery I have not Mainly because I proud of being a transgender woman and I wouldn change what I was created for
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A lot of people question my sexuality because they think that I'm gay because I'm a trans woman, because yes
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she originally was a man, we all know that. But truly, in her heart, she is a woman
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So therefore, I feel I am straight. I've never seen a photo of Alayna
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before she was transgender, no I have not. Do you want to? Yeah, let's do it
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Yeah, let's do it, because I love you and it doesn't matter. I love it. Let me see it. Yes. Look, that is a handsome man
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I will put it out there. I can say a man's handsome. I'm comfortable with my sexuality
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That is a handsome man. And if I was a girl, I would go for that guy too
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This last two years of dating a trans woman, it's been very rough. I've lost a lot. I've lost a lot
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I've lost my entire family. I lost all my friends from back at home, everybody that I thought was closest to me
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And I want their love back. I want my family and my life
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Oh, gorgeous. Gorgeous. And we get a ton of hate online. The judgment we get is that I'm gay
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You are gorgeous, baby. Yeah, yeah, flex them abs for me. Let me see a little bit of abs. Women can have abs now
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Yeah. Woo! Let's say it. Those are two dudes chilling on the couch
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Those are two dudes or two bros hanging out. Give me more muscle
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Yep, that's what I want. Definitely get a lot of comments. I'm a man, still a man, two dudes hanging out
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You are a man cosplaying as a woman. She's got a glizzy, he's gay
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She's got a glizzy, I love it. I used to be that guy with the negative comments online
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One of these people that would make fun of a guy like myself or make fun of somebody for being gay
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or somebody for being trans. And it's opened my eyes dating a trans woman to see the greater significance of someone like her
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Look at that, dude. Ain't nobody doing it like me, bro. I like a piece of that cake
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We definitely have a lot of supportive followers online. We have followers that have been in our journeys from the beginning, constantly sending us love
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This is real life stuff. People come at men like me. I will not stop fighting until trans women like my girl get accepted and looked at differently
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A lot of people don't know that I really did suffer from a bad drug addiction
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I was lost I took a lot of work to find myself and I owe it to that lady out there Well I was always religious I was born and raised Christian
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and my religion solidified when I seen him at his lowest, and I thought I was at my lowest
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The lowest of the low is watching my girlfriend have to sell all of her diamond jewelry
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and all of her designer bags so she could get me another bag or get me another shot
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And the last time that I got high, I said, goodbye, I don't want to live anymore
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I woke up 28 hours later I didn't know where I was I found God when I was in the hospital
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through the cracks of the curtains I saw my wife sitting there like this
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saying I love you, don't give up, I need you from that moment on I found it pretty important
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to try to bring God into our life because there's something bigger and greater
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out there than us and we truly believe in that around here so we're going to pray
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initially my friends and family wasn't so sure about our relationship because of his past with his addiction
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She begged, I don't know what I'm going to do with you. But she never gave up on me. Rehab after rehab
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Try 16 rehabs in six months. That's how much she didn't give up on me
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I'm just coming up on just about nine months sober because it's just about waking up sober and going to bed sober
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I've been very proud of his sobriety. At the end of the day, seeing it firsthand, his experience
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has been so rough for the both of us. Him being sober and showing me that he can do it
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proving everybody wrong, has been the most proudest moment of my life
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It's been hard. It's the hardest thing somebody will go through. It's the hardest thing I've ever been through
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I made it out. Don't give up. We made it out, so thank you
6:54
Jocelyn is one of Elena's first friends that I met. Is Jocelyn on her way right now
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Yeah, she should be here any minute. Okay, I think the last time I saw Jocelyn, I was strung out. Right
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Jocelyn has definitely doubted our relationship based on his addiction. And I remember she said, you better take care of my girl
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This is my best friend right here. I don't think she was too confident on it, honestly. Hey Carl It so good to see you It been so long Hi Jesse how are you What up girl What up
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So have a seat. When I first saw you guys get together, I definitely was skeptical
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Because the Jesse I knew back in the day was a very interesting character
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Very, very skeptical. It was very fast. Yes, it was. I think I was single for like four days, five days
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We kind of just fell into it, and it was unexpected. But obviously, I probably gave you a bad taste in your mouth
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And you know, the only reason I'm really alive is because of Elena. Of course. You saw the route I was going
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It was disgusting. It was bad. Jasmine, I want you to understand I'm not perfect, but a year and a half later, I have a lot of work with myself
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You look very different. You look very healthy. You're glowing. Life's been good
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I put her through a lot. It took a lot out of her. I told you don't play with my girl. Yeah, and I did it
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I played with her for a while and you know for some reason she stepped by because that's who Alayna is
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You know a lot of girls in our community don't have healthy relationships
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Obviously not every relationship is perfect but to have somebody who stands up for the trans community the way that you do
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when a lot of men are scared and ashamed to be with trans women it means a lot
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You know a trans woman changed my life. You know I was that guy that would make fun of men like me or women like you. I was that guy
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Look at us now, you know what I mean? I've never felt more love in my entire life
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That's so sweet. Well, thank you for having me over. Thank you for coming
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I miss you so much. I proposed to Elena at a restaurant in Miami
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in front of the whole place, on a microphone, so the whole place can hear it
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So specifically, she can hear me loud about how serious I am in wanting to marry her
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Jesse has definitely shown me what love really means, what dedication really means
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He wears his heart on his sleeve. People who judge our relationship keep doing it
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because you're only making us stronger. You're not putting a dent into our heart or souls
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You're not putting a dent into the trans community. Try to not put hateful comments out there
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Try to put something positive out there. Less hate more love. Thank you
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