From Childhood Friends to Lifelong Lovers

How Jason Earned His Best Friend's Blessing to Date His Sister

If you don’t believe in soulmates, this week’s Love Letter couple might change your mind. Jessie and Jason grew up down the street from each other on Long Island, and have been a part of each other’s lives for as long as they can remember.

From friends, to dating, to engaged and expecting their first child at 18, Jesse and Jason have been ready to spend their lives together since almost the moment they met. The couple have been together for 23 years and are parents to four kids.

Below, they tell Meet Cutes NYC about the power of love at first sight, the complications of having a thing for your best friend’s younger sister, and what they love about each other most.

How did you two meet?

Jessie: We've lived one block over from each other since we were 3 or 4 years old. And we definitely think we played together, because we had a lot of the same friends. He was best friends with my brother, and I was very good friends with his sister. And then when we were probably 16 or 17, a really good friend of mine brought him over to hang out. And I actually whispered to her “I’m gonna marry him.” I just got a really good energy from him.

Jason, what was your first impression of Jessie?

Jason: I always thought she was beautiful. But her brother was my best friend. And I felt like I didn't want to cross that line. But as the years went on and we started hanging out more, I asked for permission. And when I was blessed with that, I just went from there.

I’ve been in love with her ever since I met her. I just never felt like I was ever good enough for her. But I just knew that she was the one I wanted to be with from the get go. 

Was it hard to ask your best friend if you could date his sister?

Jason: That was very nerve wracking. I had very few friends and I just didn't want to ruin anything. And I also didn't know how he would react to that. He was very protective of her, he watched over her like a big brother does. It was huge for me. It was almost like asking her dad.

I didn’t expect him to be so accepting of it. But he was. He actually said I was the only one out of all his friends that he felt that way about.

Jessie, what was it like having a crush on your brother’s best friend?

Jessie: He was always very protective of me, and I kind of didn’t ever say anything because I was like, “this isn’t gonna happen anyway.” Because he was always like, “no,” to everybody.

What happened next? Did you start dating right away?

Jessie: We’ve been together ever since. Would I tell an 18-year-old to get married? No. But we were 18 when he proposed to me, and of course I said yes. And then – I’m not kidding – probably four days later, I found out I was pregnant with our first child.

I wanted to wait until I had the child to get married, but he really wanted to do it before. So we did get married before our first baby was born. That was in 2002.

Do you believe in love at first sight?

Jason: Yes. I’m not good at explaining myself in terms of how I feel about things. But I will tell you from the get go, since I saw her she’s been the one. I have no eyes for anybody else. She’s the only woman that I love. I’m speechless when it comes to it. And that’s 23 years later. I 100% believe in love at first sight.

Do you think teenagers should be able to make lifelong commitments like you did?

Jason: It would be very hard for me to say no to that, because I have kids that are teenagers right now, and because of how I felt. I am not that person that says “oh, you’ll just get over it.” I think [love] could happen to anybody. It happened to me. And I’ve gotta be open and understanding of that.

Jessie: I feel the same way. For us, we had very similar experiences. Growing up with our parents, we didn’t have a great upbringing. So for us, we had each other. And to this day, that’s all we have. I wouldn’t be able to tell someone they’ll get over [young love]. 

What are your favorite things about each other?

Jessie: From day one, what I always noticed about him was he is a gentleman, like the one that opens doors for you. We get up at 5 a.m. to get ready for work and he has my coffee made. He writes love letters every morning. And it's just all those simple little things that are my favorite thing about him.

Jason: We’re going to need more time, because there’s not one thing I don’t love about her. I’ll start with her heart. She’s got a heart of gold. She’s always been a motherly figure. She’s always worried about somebody else. I love the fact that she’s beautiful no matter what, inside and out. She’s got the greatest ears, eyes, nose, lips. She’s got the greatest mind. She’s very smart. She’s just all around a totally, totally beautiful person.

I love every square inch of this woman. She is my queen. The best way I can put it is I would do anything for her. I know it’s said a lot but I would literally lay down my life for this woman if I had to. She’s totally worth every second of my time. There’s not one thing I don’t love about her. She’s just the sweetest person in the world.

Do you love the same things about each other now that you did when you were 16?

Jessie: Just from being together for so long, it’s like we kind of grew up together. We’ve just learned so many more things about each other.

Jason: It’s like it’s grown more. We started out with love, yes. But it’s just grown over the years. Obviously through life it’s not always peaches and cream. You have your ups and your downs. But love grows over time more than anything.

Do you have any advice for someone who wants to express their love to a crush?

Jason: Do it. It’s easier said than done, I understand that. But you’ve gotta follow your heart, you’ve gotta follow your mind, you gotta follow what you believe. I can’t explain it. When it happens to you, you know it. You just feel it. I personally say just go for it. You never know what’ll happen.

The best love is the kind that awakens the soul; that makes us reach for more, that plants the fire in our hearts and brings peace to our minds"

The Notebook

🤔 Poll of The Day:

Have you ever had a crush on your friend’s sibling?

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📊 Last Week We Asked…

Do you think it’s important to share your main interests with your significant other?

  • 57% said “Yes! Shared interests are a must”

  • 43% said “No! Enjoying different things is fine”

And one meet-cuter shared:You don't have to be joined at the hip but it is super important to have some things you do share and love is fundamental to growing in the relationship.”

Do you or someone you know have a meet-cute story for the Love Letter? Get in touch here!

Interviewed and transcribed by Nicolas Vega. This interview has been edited for length and clarity.