A Candid Conversation with Jack Stone, Bachelor Nation’s Nicest Jewish Boy

As a reluctant fan of the Bachelor/Bachelorette franchise—I have my college roommate to thank for getting me hooked on the reality series—finding out contestant Jack Stone was Jewish was like finding out someone I grew up with decided to try his hand at reality TV dating. When I got the opportunity to talk to Jack Stone, I couldn’t wait to find out how a member of the Tribe ended up as one of the 31 men competing for Rachel Lindsay’s heart on the Bachelorette (and then competing for I’m not sure what on Paradise).

Jack walked his goldendoodle through Dallas as we spoke about Bachelor producers, Jewish matchmakers, the best bagels in Texas, and everything in between. Soon after we started talking, Jack asked me if I watched any of the Bachelor franchise shows, and when I told him I was a fan, he responded, “Oh my god, I’m sorry. It’s such a terrible show. I always make fun of people.” So set the tone for a candid conversation with Bachelor Nation’s most eligible Nice Jewish Boy (who’s not a serial killer, I promise).

How did you end up on the Bachelorette?

My cousin was on the phone with me and was like, “You need to do something different, go out on a limb and try something new. You should go on a TV show,” and I was like, “What are you talking about?” and she was like, “You should go on a reality show of some sort.” And she [adds], “Why don’t you apply for the Bachelorette.” So we’re on the phone together, she Googles it and there’s a short form. She sent me the link and it took me like five minutes to apply. The next morning, I got a call and it was an LA number—I thought someone was just screwing around with me—and one thing led to another. I was actually supposed to go on Jojo’s season originally, and I had to back out last minute.

If you could talk to Jack a year ago, going into taping the Bachelorette, what would you say? Would you have done anything differently?

You know, time will tell. I’m still wondering whether I would’ve even gone on this show. I think if I went and did it differently on the Bachelorette, I would’ve gone in as a complete joke from the beginning, done something really goofy and off the wall. When you do that, it automatically takes the pressure off you; it shows that you’re not taking the show that seriously. It is very hard to mess with someone who is already messing with themselves. Had I come in a penguin outfit, it would’ve been very hard for anyone –all the powers that be—to try and edit me to make me look funnier or worse because I’m already kind of making fun of myself.

After Bachelorette, why did you decide to go on Bachelor in Paradise?

That time @amanda_stantonn and I acted out other people’s conversations on the beach 🌴☀

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Once you’re there, you’re kind of all in—I mean, I never thought I would be doing Bachelor in Paradise. But, I had already put so much out there and already risked so much in going on the Bachelorette that it was kind of like, at this point, fine. Because my final episode of the Bachelorette didn’t air until I was already in Paradise without a phone, all I knew [going into Paradise] was that I thought I went home earlier than I should’ve gone home, but I didn’t know the edit. I was basically being told by all the producers that it was going to look really good. So when they were like “come to Paradise,” it wasn’t really like a hard decision for me to make.

On Bachelor in Paradise, were you frustrated with the fake serial killer edit?

It just got so old, so ridiculous. I get so many comments like, “I don’t get it,” or, “This is absurd, you seem like one of the most genuine best all-around guys there.” The show, at the end of the day, is a comedy; Paradise is a comedy with some drama in it. Whereas the Bachelor/Bachelorette is a drama with some comedy in it. So Paradise is not supposed to be taken too seriously—you have the serial killer, a penguin, pizza running on the beach, a dolphin shark girl, a scallop fingered girl… It’s just the most absurd, weird stuff. [The serial killer plotline] was frustrating to me because I didn’t think they needed it.

Do you think it negatively impacted your time on the show?

I don’t know what everyone’s agenda was [on Paradise], but I promise you, to find love is not number one. Hopefully it’s close to number one—but it’s not number one on the list. And so [the serial killer plotline] put me at a net negative, because no one for the cameras is going to be like, “Oh, it’s a serial killer! I’m gonna act like I’m into serial killers!” It puts you at a disadvantage. In real life, I know who I am. And in real life, I know what would really happen, but this isn’t real life, this is in front of cameras and TV and people with their own agendas. So, that was frustrating.

Do you believe people go on the show for the right reasons?

People forget that [the producers] are not in the business of matchmaking—they’re in the business of entertainment. They need the show to be entertaining so they can get viewers, so they can get ads, and so they can get money. The mere fact that 75% of the cast is chosen before they even know who the Bachelorette or Bachelor is should be all you really need to know. People need to remind themselves that what they see is not always real life; just because the word “reality” is in the show doesn’t mean anything. Yes, there’s some reality in it, yes there are some success stories from the franchise, and that is a beautiful thing. But that doesn’t mean that everything you see is real; it just means that the show is a shot in the dark and sometimes there can be a success story.

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In our original article that we ran on Bachelor in Paradise, we ranked Jewish contestants based on Jewish geography. You tweeted that there was a reason you changed your last name from Oberstein to Stone. Can you clear up the switch?

My dad was one of three kids, and he was the only boy. He was the only Oberstein left, he changed it to Stone, and I just followed suit, because then I would’ve been the only Oberstein. It became a joint decision and something that we did together. The name change was something that he had wanted to do since he was a kid, but he was finally in a point professionally in his life where he could do it. It was a way to symbolically start all over with the family name because of the relationship that he had with his father and the relationship that basically my whole father’s side of the family had with their father, which wasn’t a good one. Stone was chosen cause Oberstein means “over stone” [in German]. So, Stone was still a Jewish name. It wasn’t like “Johnson” or something like that. It was definitely weird at first and now it’s just like completely normal.

Would you ever use a good old Jewish matchmaker?

You know, I have before. I’ve had a couple different good old Jewish matchmakers [laughs] contact me before and try to set me up, and I always felt like they were trying to do the other person a favor. A lot of girls feel the same way about matchmakers, or people that try to set them up… [laughs] who are they trying to help out here?

Does your family pressure you to marry Jewish?

It is definitely a bonus! My dad’s side is Orthodox and they live in New York, and my mom’s side is very secular, and they live in Texas. I’ve grown up seeing both sides of the spectrum that I don’t think a lot of people get to see. On my dad’s side, it’s definitely encouraged, and on my mom’s side, it’s not weighted as heavily.

How do you feel about dating Jewish?

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I think it’s always a bonus because it’s one less thing to have to learn about each other. One less thing to have to give or take when you decide how to raise your family. Just like anything else, it just gives you more in common. If you’re Jewish, and you meet someone else who is Jewish, there are certain unsaid things that you just get. And it doesn’t have to be explained. My most serious relationship with anyone—she wasn’t Jewish, but she was always open to learning.

What was your experience as a Jewish contestant on the show that is largely not Jewish?

Well, you should take a step back. First, three out of four producers are Jewish. It’s Hollywood, right? They’re all Jewish! Behind the camera, there’s the casting producers who are hanging out with the cast and pulling the strings, and a big chunk of them are Jewish. Some of them are Israeli even, and speak Hebrew fluently! For a lot of cast, year after year, the only experience they’ve really ever had hanging out with anyone Jewish is coming on the Bachelorette or Bachelor and meeting some of the producers. Think about that! I don’t know if you remember on Bachelor in Paradise, Iggy reading—trying to read—a Hebrew prayer…

Yep. Cringeworthy.

You know who that was? One of the Jewish producers who thought of that. By the way, I told Iggy not to do it, cause I thought it was gonna come off as mocking. I think the way it came off was funny and ended up working out just fine, but it could’ve gone the other way.

Outside the world of “reality” dating, what would your ideal date be?

An ideal date is something that just flows. Anytime you go on a date and you have to overthink it, it might not be a good thing. The ideal date, really, turns on the conversation. If you can have a really good conversation with someone, and really hit it off with them, that really makes such a big difference. We’ve all gone on dates where it’s like pulling teeth versus going on dates where it just feels right. I remember with my ex-girlfriend, we essentially had a 48-hour date; we just didn’t want to be away from each other because we were having such a good time.

What’s your ideal bagel?

You’re going to hate me for this, but I just go plain all the way. Plain bagel, plain cream cheese. Sometimes I like lox with a slice of tomato, and it’s gotta be seasoned properly with salt and pepper and capers. We don’t have good bagels in Texas, though; you guys in New York have better bagels.

What is one thing you wish people knew about you?

I wish people knew about my mom. Everybody got to find out about Dean and Dean’s mom story; they never got to hear about me going through a very similar situation, but as an only child. I lost my mom when my parents were divorced, and moved in with my dad when she passed away. I had to put myself through college. None of this was easy for me. I feel like that story is a huge part of my life and defines who I am today. I also wish more people knew that I’m actually a pretty funny guy in real life.

A truly amazing mom. Miss her every day.

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Last, a quick word association. What do you think of when I say “Nice Jewish Boy”?

Can I say me?

This interview has been edited and condensed.


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