There are few things more awkward than telling a grown man you’re about to ask him a series of questions best saved for a second or third date. Especially when that man is Jared Padalecki, the chiseled-jawed heartthrob you’ve been watching on television for over half your life. But this is Glamour’s Inappropriate Questions column, and this writer has a job to do.

“Game on,” Padalecki challenges over the phone, instantly clearing the air of any nervous tension. In fact, he says to “be prepared” as if I’m the one about to be put in the hot seat. His lack of caution is disarming but not completely unexpected. The actor got his start in Hollywood in the early aughts playing Rory Gilmore’s first great love on Gilmore Girls. After five seasons he left the series to hunt monsters as Sam Winchester on Supernatural, which just ended its 15-year-long run in November. Considering the fanaticism surrounding both projects, there’s likely no question he hasn’t already been asked by the press or fans.

“I’ll have even more inappropriate answers. You’re gonna have to have a lot of asterisks in your article,” the 38-year-old jokes with a deep laugh. It’s easy to picture the laid-back, Texas-boy smile on the other end of the line.

Despite initial plans to retire after well over a decade of filming Supernatural in Vancouver, Canada, Padalecki was sucked back into acting almost immediately by his latest project at the CW. He stars in and serves as an executive producer on Walker, a modern reboot of the Chuck Norris martial arts procedural, Walker, Texas Ranger. But vocation is pretty much the only thing the two shows have in common.

Padalecki’s Walker centers around a grieving widower who struggles with the death of his wife (played by his actual spouse, Genevieve Padalecki), raising two teenagers, and balancing his duties as a law enforcement officer. The drama, which premiered in January, has already been picked up for a second season and will be filming an additional five episodes for season one.

But what was it about this particular property that halted Padalecki’s plans for a long-overdue break? Well, for one, the headquarters of the Texas Rangers is in Austin, where he and his wife are raising their family. “It’s a great sleep in my own bed. It fucking sucks to wake up because the kids are running around and jumping on my head, but it’s awesome,” he says. “I feel like towards the end of Supernatural my thought process was like, Man, I have a wife and three kids—I’d like to meet them.”

It turns out, dating your partner again after 10 years of marriage has its advantages. During our call, Padalecki opens up about his ideal date night, working with his wife, and even confirms a long-rumored Gilmore Girls romance. My one goal: surprise Jared Padalecki.

Glamour: Before COVID-19, you were doing almost 20 Supernatural fan conventions around the globe each year. What’s the wildest thing a fan has ever asked you?

Jared Padalecki: I have had a few people ask me to sign something on their body or draw something for them to get tattooed—and then I’ve seen the tattoos! I haven’t tattooed anybody…well, I did tattoo my friend Bruce, and he tattooed me. But that’s neither here nor there.

How much experience tattooing do you have?

Zero. We finished filming Supernatural forever on September 10; on September 11, he was like, “All right, have an appointment for us to go get tattooed, buddy.” So we went and got tattoos, and he did a little dot on me and I did a little dot on him. Luckily it wasn’t something that needed any artistic talent whatsoever.

Let’s talk a little bit about Walker. The premiere was the most watched episode on the CW since 2018 as well as the network’s highest-viewed series debut in five years. Why are people so obsessed with you?

The big forehead. [Laughs.] I think a lot of people in the world right now are really looking for something to feel good. My Walker is not the Chuck Norris Walker, where he walks around roundhouse-kicking people randomly. Our Walkers are not even related or connected.

My Walker is a guy who’s flawed and trying to do the best he can in a world that’s hard to navigate. I think it’s a universal theme. Whether you’re law enforcement or a parent or not, you can find parallels to your own life in somebody who’s just a little in over their head and trying to be the best they can in difficult circumstances.

You actually had a Walker, Texas Ranger moment on Supernatural and now you’re leading the reboot. Do you have a cowboy kink?

A cowboy kink? I’m not sure what that means…I’ve got three young kids, man. I know what Frozen is and I know what Paw Patrol is, and that’s basically it. Kink…like a fantasy?

Yeah!

Okay, cowboy kink. [Laughs.] You know what? Cowboy boots on a woman are very sexy. When I started dating Gen during Supernatural, she had these—she still has them, I think she wore them on Walker, as a matter of fact—she had these cowboy boots with skulls on them. I was like, Damn, girl.

There’s something that just melts me in all the right ways when you see a woman who’s beautiful and soft and caring and has some badass cowboy boots on. So that’s probably my kink.

You met your wife when she played Ruby in seasons 3 and 4 of Supernatural. She appeared a few more times throughout the series, but what is it like to really act alongside her again on Walker?

It’s pretty awesome. Gen’s such a strong woman. I mean, she was a double major, double minor, college soccer player. The first marathon she ever ran was the Boston Marathon, and she missed qualifying by two minutes because her Apple Watch died or something. She’s given natural childbirth multiple times. She is so much more tough and badass than I am, so seeing her in her element is so sexy.

I have to imagine, after spending so much time in Vancouver, you’re almost re-dating. Do you guys do anything special for date night?

When we really want to have a special night, we will get a hotel room. [The night after the Walker premiere], we went out to the Lake Austin Spa. We got a babysitter for the night, and we’re like, “We’re gonna get a massage. We’re going to watch a movie in the room, sleep, get in the hot tub, whatever, and we’ll come home around noon to go watch our son’s basketball game.”

Okay. It’s time to get really personal. Are you ready?

I’m in. I’m sitting.

In 2016 the casting director of Gilmore Girls, Mara Casey, gave an interview in which she said, “We did have a running joke about casting all of [Alexis Bledel’s] real-life boyfriends. She dated Jared and [Milo Ventimiglia].” Is that true?

It is true! But I had never met Alexis before the show. We did date, but they cast me as a human being, and then I became a boyfriend.

When Alexis and I met, we were both 17 years old and were both Texans and kind of in this new, strange city and I was like, “Hey, want to go out to dinner?” I know she dated Milo for a while and yes, she and I did date.

Before or…?

It was before because he wasn’t on the show until season 2. I think we dated during season 1.

How did you two keep it a secret?

I don’t know if we tried to keep it a secret. I wish it was scandalous or something! I think it was more kind of silly. We were two 17-year-old kids who were like, “Hey, you want to go bowling?” It wasn’t anything super juicy.

You’ve said multiple times that you’re Team Jess over Team Dean. But do you feel like we, as a society, should still be Team Rory? She kind of sucks too.

I laugh when people are like, “I’m Team Dean.” Dean cheats on his wife! And Rory didn’t help.

Rory had some issues. You know, she was a kid growing up and trying to navigate her way in a weird world without a really solid father figure and with a kind of kooky, neurotic mother. I’ll say this: Yes, I’m Team Rory. I think Rory was trying to live her life, and she wasn’t malicious. She wasn’t one of these mean girls who were like, “Oh, I’m gonna start a rumor about this person or that person. I’m gonna try and ruin this life.”

Did she make some mistakes? Fuck yeah! Of course! We all do. She probably hurt some people, she probably got hurt. But I think she was just trying to live her life and figure it out. She wasn’t outwardly trying to hurt people. So yeah, call me Team Rory.

So did any of these questions manage to surprise you?

I think so! That Alexis boyfriend question. I didn’t know Mara had said that.

This was four years ago—you can’t get mad at her!

Yes, so the statute of limitations on this has long since passed.