Chilina Kennedy and Jacob James — High School Sweethearts With Some Stops Along The Way | Playbill

Showmance Chilina Kennedy and Jacob James — High School Sweethearts With Some Stops Along The Way Love at first sight, awkward kisses, frantic attempts to stop a marriage, divorce and a romantic reconnection. No, this is not the elevator pitch for a new Jason Robert Brown musical, it's the real-life story of how actors Chilina Kennedy and Jacob James met and fell in love.
Jacob James and Chilina Kennedy as teenagers

When James was just 14 years old he knew he had found the girl he was going to marry. She was the 16-year-old Kennedy, who was starring in his high school's production of Anne of Green Gables. They went on to share the high school stage (and Kennedy's first onstage kiss) as Rose and Albert in Bye Bye Birdie, but it took almost 20 years for Kennedy to realize James was the one.

Now that the two Stratford Shakespeare Festival alums are finally together, they are happier than ever. Their long history has helped the Kingston, Ontario natives to create an unbreakable partnership that stands up to the highs and lows of show business and the challenges of balancing career and parenthood. At the beginning of March, Kennedy stepped into the demanding role of Carole King in the hit bio musical Beautiful: The Carole King Musical on Broadway, while James, who currently lends his voice to the children's cartoon "Fireman Sam," is staying home to take care of their six-month-old baby boy, Henry.

Kennedy and James explain how, after a very long and emotional journey, they finally reached their happy ending.

Chilina, congratulations on becoming a new mother and landing the role of Carole King in Beautiful!
Chilina Kennedy: It's funny, life is imitating art: Carole King had a five month old in the show. I keep joking that I'm going to find ways to get the baby on stage. And like Carole, you are balancing a thriving career and motherhood. How are you able to do that?
CK: We have people like Carole King to thank for paving the way for people like me. And honestly I couldn't do it without Jacob. We have a great system. When Henry was born Jacob was working on a play, and then seven weeks after I gave birth I did Mary Poppins in Canada, then I took a little break and Jacob did another play, and now I'm doing Beautiful. We've been quite good at handing it off between each other, but it takes a real generous spirit to say, "Take this year to do a dream role on Broadway and I'm going to stay home and take care of the baby." It's pretty wonderful. I've got a great modern man who's comfortable with that.
Jacob James: Well, I've been after Chilina since I was 14 years old, so it's worth it to me.

You were only 14 years old when you met?
CK: It's quite the story actually. We've known each other for over 20 years. We met in high school. I was the older woman. I was 16.
JJ: As cliche as it sounds, she was my first true love. When I was in grade eight I saw her in a production of Anne of Green Gables at our high school in Kingston, Ontario. I hadn't met her, but I was watching her on stage and I said to myself, "That's the woman I will marry and have kids with one day." It wasn't so much that I hoped it was; it was like I recognized her and I just knew.
CK: It was funny because after high school we went our separate ways. I ended up getting married to somebody else and Jacob and I weren't together for years. We've only been a couple for about three years. My first stage kiss was with Jacob, though.
JJ: We played Rose and Albert in Bye Bye Birdie in high school.
CK: It was the most awkward thing you could possibly imagine. We kind of went in in the moment to kiss and right at the last moment I turned my face to go the same direction as him. We whacked our noses together and started laughing in front of the whole auditorium.

Did you know that he had a crush on you at that time?
CK: He was pretty clear with his feelings from the beginning. He was a very bold 14 year old.
JJ: That was the trouble with being the younger guy at that time in life, because it just doesn't work that way, so I suffered a bit of heartbreak as a kid. I kept fighting that knowledge that we were supposed to be together, but circumstances were not reflecting that. It got to the point where she went off to Sheridan College [in Oakville, Ontario] and I went to the National Theatre School [in Montreal] and we kind of lost touch. Then, when I was doing my first job out of theatre school, I found out she was getting married. I was in a car commuting with a bunch of other actors to a production of the Scottish play in Toronto and she was in San Francisco at the time, so I called her up with my first big Motorola cell phone and told her she was making a horrible mistake and she shouldn't get married because she was supposed to marry me.
CK: It sounds so dramatic. It was a scene right out of a movie. I was like, "What is going on? I can't believe you're calling me and trying to stop the wedding."
JJ: So, she went ahead and got married anyways. Then we went on our separate paths, but we were always in each other's lives.
CK: Years later we find out we're both single and now we're together. Two actors living a life can be complicated at times, but we've been able to make it work.

James and Kennedy with Henry

Jacob, had you been in touch with Chilina when you called and told her not to get married?
CK: No!
JJ: That was the main retort of the whole thing.
CK: He called me out of the blue after two years of silence. [We weren't talking] because he needed to get over me, but I didn't know that at the time. All I knew was that he had sort of dropped off the face of the planet. Then he calls me and he tells me not to get married. We got into a fight and I hung up on him.
JJ: It was tough in high school because I had to watch her date some older bad boys and all that so when I finally left high school and I got to Montreal, I was like, "OK, I'm living my life now."
CK: Living the dream!
JJ: I needed that chapter, but she's always had my heart.

I have a perma-smile on my face listening to this.
JJ: They should make a Broadway musical about it!

Yes, and you guys can star! How did you reconnect after Chilina got divorced?
CK: This is a funny story too, because we were plagued by not being in the same place at the same time. He was at the Stratford Shakespeare Festival for six years. I had a chance to go there, but I decided not to. I was at the Shaw Festival Theatre, but I ended up joining the Stratford company just as he was going to New York. Then I ended up going to New York with [the 2012 Broadway revival of] Jesus Christ Superstar, just as he was leaving New York to go back to Stratford. We were always passing like ships in the night, never being in the same place at the same time until we were meant to be together, which was three years ago. We were both single, we had lunch and that was that. I thought, "Oh my gosh. Where has this man been my whole life? I'm supposed to be with him."
JJ: There's a quote from a play I love and I've done a couple of times called The Zoo Story by Edward Albee and I think it sums up the experience to a degree. It says: "Sometimes it's necessary to go a long distance out of the way in order to go come back a short distance correctly." With the two of us, it was a matter of being ready for each other. It was also a lesson that if you have a deep conviction that something is supposed to happen and then it doesn't, it doesn't necessarily mean that it won't happen eventually. You might just have to do some things in the interim to be ready for it.

Very true. Chilina, your parents also met when they were really young, right?
CK: I know, it's wild isn't it? My parents tell stories of walking to school together and being in the same class. I was always so envious of that. I thought it was so sweet to know somebody that long and to have that trust and history together and then here we go. They met in grade four so it's not quite the same, but I have certainly known Jacob for a long, long time and it's just wonderful.

What is one of your favorite memories from when you were younger?
JJ: For me, the first thing that comes to mind is when my dad, who is a musician — his name is Roger James — was playing on a cruise ship in Alexandria Bay, which was close to the U.S. border. It was the 4th of July and the captain knew that I was there with the girl I was in love with, so he let me have the run of the ship and we lit fireworks off of Heart Island.
CK: It's funny because I didn't even know we were on a date. I was like, "Oh my gosh, this is a date. This is really romantic." It was pretty wonderful I have to admit.
JJ: We might have kissed a bit in the back of the car when my dad was driving us home, which probably made my dad feel pretty awkward.

Kennedy and James

Do you think having this history with each other helps you to have a solid relationship in this crazy show business world?
CK: Oh absolutely. I think it keeps us grounded and who we are and not affected by the ego hikes or the ego lows.
JJ: Also for whatever amounts of success that either of us have individually, our foundation started way before any of that happened.
CK: Yeah, it's not a show crush or it's not a love based on, "Oh my gosh, he's so talented," or any of that sort of stuff. It's really based on who we are as people.

After all this, do you guys want to get married?
CK: We actually planned on getting married last summer but we ran out of time.
JJ: We're both pretty busy actors so we want to find the time to get married where neither of us has a two-show day the next day, We're talking about waiting until Chilina can take some time from Beautiful.
CK: It's just about finding a good time where we can actually do it and have a little honeymoon afterwards.
JJ: On one other romantic note, we are engaged and the ring that I proposed to her with is the ring that my Grandpa proposed to my Grandma with. Both of my grandparents passed away, but they were super close to me.

That is so sweet! Chilina, when you got pregnant last year you had to back out of a few Stratford Shakespeare Festival shows. Were you guys planning on having kids at that time?
CK: We were wanting children, but the specific timing of it was a surprise. We were wanting to do it later, when the season was done or nearing an end, so it was a bit of a surprise — but a thrilling surprise, of course. We really wanted to start a family, so we're very grateful, and he's the best kid in the world. We're so blessed. Last night there was a party to welcome Jessica [Keenan Wynn] and I to Beautiful and everyone was asking how I was doing with the baby and everything, and truly we are so lucky. He's a great sleeper, and he's got such a great personality. He's really easygoing, so it kind of allows us to be easy going too.
JJ: He's still got teeth to come in, so we'll see what happens. Knock on wood.

A First Look at Beautiful's New Leading Ladies, Chilina Kennedy and Jessica Keenan Wynn

Do you sing or perform for Henry at home?
CK: Oh, we do it all. Jake is the king of impressions and different voices so he does all kinds of crazy impressions and dialects with him and I end up singing a lot. It's really fun and Henry loves it! It's ingrained in him because I was performing concerts and I starred in South Pacific when I was pregnant.
JJ: He has his unofficial Equity card. He did so much when he was in her belly. I can't help but talk to him in funny voices because that's kind of my bag as an actor is character stuff. He'll know three different dialects by the time he's speaking.
CK: No pressure, of course!
JJ: I'm very keen on gently introducing Shakespeare at an early age, because that's what I spent my twenties doing.
CK: He's a great Shakespeare teacher, so he's got a lot of things to look forward to, this kid.

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