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Home Entertainment

Milo Ventimiglia and Arielle Kebbel Dish on ‘Gilmore Girls’ BTS Secrets

by DigestWire member
February 20, 2026
in Entertainment
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Milo Ventimiglia and Arielle Kebbel Dish on ‘Gilmore Girls’ BTS Secrets
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Milo Ventimiglia and Arielle Kebbel play a happily married husband and wife in their new film I Can Only Imagine 2, but the pair once found themselves entangled in one of the messiest — and juiciest — love squares in teen drama history.

Kebbel, 40, and Ventimiglia, 48, shared just one scene on the early-aughts darling Gilmore Girls, in the 2003 season 3 episode “Keg! Max!” In it, Ventimiglia’s broody Jess mocks Kebbel’s Lindsay for liking the band Matchbox Twenty, then gets into a fistfight with her boyfriend, his nemesis Dean (Jared Padalecki). Oh, and did we mention that Dean is also Jess’ girlfriend Rory’s (Alexis Bledel) first love? Like we said — messy!

“Who knew we’d be sitting here now?” Kebbel asks Ventimiglia as the pair talk to Us Weekly exclusively about their onscreen reunion as husband and wife in I Can Only Imagine 2. It’s a follow-up to the 2018 faith-based film about real-life MercyMe front man Bart Millard and his iconic 1999 song “I Can Only Imagine.” In the sequel, Ventimiglia plays musician Tim Timmons, who tours with the band while battling cancer. Kebbel plays his wife, Hilary.

Here, Ventimiglia and Kebbel interview each other about forging a new bond, reflect on playing Gilmore Girls characters fans love to hate and even entertain the unthinkable: What if Jess and Lindsay had run off together?

Milo Ventimiglia: My ‘Gilmore Girls’ Character Jess Was a ‘Child’

Milo Ventimiglia: Arielle, do you remember when we met that very first time, a long time ago?

Arielle Kebbel: I think it was the ice-skating rink [in season 3 of Gilmore Girls].

MV: It was the ice-skating rink.

AK: I got the job a day before. We were on set, but I didn’t kiss you.

MV: Well, that would have spun the whole Gilmore-lore world into a whole other place.

AK: They would have hated me even more. Because, let’s face it, they hated me. But I kissed Dean.

MV: What are you gonna do? It’s OK. And hey, it was Jared.

AK: True. I actually accidentally called him Dean in Hair and Makeup when I met him because I was so nervous. I was playing it cool, like, “What’s up, Dean?”

MV: Did he have a reaction to that?

AK: No, he was really nice about it, because that’s who Dean is, and that’s who Jared is. He was my first onscreen kiss.

MV: Oh, wow. What a first day.

AK: Now you play Tim Timmons in [our film], who’s based on the real guy. We’re the fake Tim and Hilary, they’re the realies. What I’ve seen is how special the bond between you [and Tim is]. It seems like you guys are besties.

Milo Ventimiglia and Arielle Kebbel Dish on 'Gilmore Girls' BTS Secrets
Jake Giles Netter

MV: We’ve kind of become one, right? You know this from playing Hilary — they are such lovely people, and they have such a wonderful family and the entirety of them is inspiring. Being a new parent, I’m like, “Man, I want my kids to be like the Timmons kids and [have their] parenting style.” But Tim and I, we went into [this movie] with open hearts. It was important for me to get to know Tim and the most fundamental level of his essence and his spirit, and then pick up all the little quirks.

AK: And you shaved your head!

MV: I buzzed my head, and I grew my beard.

AK: Every time I looked over at you guys on set, you were cracking up or you were playing guitar together or you were doing his podcast. It was incredible to see. You were two peas in a pod.

MV: Literally one of the best gifts of the film was being able to [say], “Oh, I’ve got a new friend that I’m gonna know for the rest of my life. This is awesome.”

AK: I really saw that. The other thing I love is the way the real Tim and Hilary are so joyful with each other. I thought, How cool that this couple who go through so much grief together also share so much joy.

MV: Absolutely. They’re wonderful people. But I was wondering, what was the best part about being married to me?

AK: Well, gosh, honestly, part of why I was so excited to do the movie was I felt like we had such sweet scenes together, and there was so much joking. [There’s a deleted] scene where you throw a smoothie at me. I have never had anyone throw a smoothie at me. I remember when they called cut, I was genuinely laughing, and it led into such an intimate scene between us.

MV: When they discover Hilary’s pregnant with their first baby.

AK: In terms of memories, I really loved that a lot, but I just loved laughing with you. It was fun to play like that.

GILMORE GIRLS (spinoff), 'Here Comes The Sun', Milo Ventimiglia. Season 3, 2000-2007 Warner Bros.
Milo Ventimiglia Warner Bros./Everett Collection

MV: And that’s very much the spirit of who Tim and Hilary are.

AK: Yes.

MV: It’s hard to pick a single [best] moment. We had so many. Even little asides that [you] and I would have by the tour bus when you’re pregnant. I don’t even know if it made the movie, but you’re pregnant, and I kind of rub your belly for luck. And then you rub my head for luck.

AK: And then another time you kiss my belly. Every take was a little different.

MV: It was so playful. None of that was scripted. But also, it’s a powerful story about music. Was there ever a song for you in the history of your life that helped you get through a tough time?

AK: When we wrapped the film, I went home and blasted [our costar] Trace Adkins’ “Honky Tonk Badonkadonk” and danced around my house on repeat, and just felt so sexy. I was going through some stuff, and it lifted me up.

MV: By the way, that still remains one of my infant daughter’s favorite songs. Oh man, she moves. She boogies to it. She loves Trace.

AK: I knew I liked her. OK, as much fun as it is talking about I Can Only Imagine, let’s get back to Gilmore Girls and give the people what they want.

MV: Here’s a question: How did you feel about coming back into the show to marry Dean? Was that season 4?

AK: I think it was. I was not a regular on it. You weren’t a regular at that point.

MV: I only did two seasons as a regular, seasons 2 and 3, and then I would pop back because [creators] Amy Sherman-Palladino and Dan Palladino would call me.

Jason Kempin/Getty Images

AK: Because they love you!

MV: They’re wonderful people who were always just like, “Do you wanna come back?” Yeah, of course.

AK: [Dean and Lindsay] were a very new relationship. I also think we were 18 in the show. I remember my mom was with me on set because I’d just moved out [to L.A.], and I put on the wedding dress and she cried. And I was like, “Mom, you gotta stop!”

MV: Did your mom also go up to Jared and tell him, “Hey, this is her first wedding, treat her right”?

AK: No, she only did that with [our first] kiss. She told Jared it was my first onscreen kiss, and I was mortified. He loved it, but then it was really sweet. It was so quick, and I remember I was nervous, but Jared just made it easy and fun. Like just another day of filming.

MV: Did you get vilified [by Rory-and-Dean fans] for marrying him? You got some grief.

AK: People hated me. It’s only recently that people have said, “Justice for Lindsay,” and I’m like, “Yes!” MV The [original viewers] that are in their 30s or 40s now, they hated you.

AK: Yes.

MV: But the kids that are watching the show these days are like, “Justice for Lindsay.”

AK: They’re the smart ones.

MV: They’re gonna change the world.

AK: Do you remember our scene together? It was about a little band called Matchbox Twenty. Am I striking a chord?

MV: I mean, the funny thing is, for both of us, that was, how many years ago — 23 years?

AK: Or five.

MV: My hairline wishes it was five. But I remember we didn’t have a whole lot of onscreen time together … because Jess and Dean didn’t really dance much together.

Arielle Kebbel Is Living for Serial Killer Edit of Gilmore Girls’ Dean

AK: It was very much Lindsay and Dean, Jess and Rory, what’s gonna happen? Hashtag Team Jess.

MV: I remember Jess saying something snipey about you. He was kind of a jerk.

AK: I didn’t think that. I just thought he was the guy in the leather jacket vibes. Did people think you were a jerk?

MV: The only time in my career I’ve ever had somebody walk up and say, “Hey, are you that guy from Gilmore Girls?” And I’m like, “Oh, yeah.” And she goes, “Oh my god, I hate you.”

AK: I had that too! At a Coffee Bean.

MV: I was at an LA Fitness. And I’m like, “Oh, thanks.” And then I walked away going, “I did my job.” Because that’s Jess.

AK: You did your job.

I Can Only Imagine 2 is in theaters now.

This interview has been edited for clarity. 

 

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