These days, marrying your high school sweetheart is pretty unusual. For it to happen three times in the same family? Downright rare. But that was the case for Newton’s Yarmush family: Brothers Ruby, Gaby and Josh married Shayna, Talia and Leslie—with the most recent wedding (between Josh and Leslie) happening last week.

The trio of lovebirds each met as teens at Brookline’s Maimonides School. This is a time usually reserved for raging hormones, bad breakups and much drama. And while the Yarmush’s high school years were typical in many ways, these couples somehow persevered.

Newlyweds Josh and Leslie graduated in 2009; Talia and Gaby graduated in 2002 and got married in 2007; and Ruby and Shayna graduated in 2000 and got married in 2004.

“We all married our best friends,” says Talia.

I sat down with the whole family (including proud mom, Debby) to learn their secrets.

Debby: My three sons went to Maimonides through high school. It has a dual curriculum of Judaic and secular studies. It’s a very long day! And they were all involved in sports and extracurriculars. You’d think that, by the time they got home late at night and had to eat dinner and shower and then do piles of homework, that there might not have been time for socializing. But I used to find them in the morning, with the indentation of a phone in their cheeks and drool all over the place. I love these three wonderful women connected with my sons. 

How was the most recent wedding?

Debby: It was magnificent. Fabulous. Very, very joyous.

As a parent, what drew you to the school? Probably not the dating.

Debby: We’re modern Orthodox Jews, and this is the school in the Boston area that’s the best fit for our beliefs and our values. 

Let’s hear everyone’s love story.

Leslie: I was dating another boy in our class freshman and sophomore year of high school, and he broke up with me because he told me that I had a crush on Josh. 

Talia and Gaby were getting married. Talia’s sister is my best friend from growing up. And so I grew up with Talia, and I invited myself to their wedding as Josh’s date. 

Oh my.

Josh: Our first date was at Ward School Park. We had a picnic together. My elder brother, Ruby, drove us to and picked us up from the date—even though it was two blocks from our house.

Talia: I want to interject. I don’t know if any of the rest of the Yarmushes know this, but Gaby would literally have his mom make us tuna sandwiches for our park dates.

What is it about tuna sandwiches? 

Ruby: I actually don’t eat tuna. I won’t even be in the same room with tuna fish.

Josh: Our first date was 2007, and I actually was going away for the summer on a trip to Israel. I didn’t stop talking about Leslie throughout the whole trip, and I bought her a necklace. I gave her the necklace when I got back from Israel and asked her out. 

Debby: She attached the necklace to a bouquet at her wedding.

So you started dating in 2007 but just got married now?

Leslie: It’s been off and on for 15 years. We’re good to go now.

When you meet someone in high school, you’re still young. You’re figuring out what you want. What’s your take on high school romance?

Josh: We dated for a number of years. We broke up after freshman year of college, and then dated again for a little while in the middle of college and then broke up again before college was over.  

Leslie: We had to grow up a bit.

Josh: But we were also consistently drawn to each other throughout, whether we were dating or not dating.

What made the most recent dating stretch stick?

Josh: Good question. At least, for me, it was more about my own maturity. It wasn’t really a question about Leslie. It was more of my own being ready.

Debby: At some point when they broke up, my comment to Josh was that it is not a family requirement to marry a Maimonides high school sweetheart. Just in case he wasn’t sure.

How did the wedding go? 

Leslie: It was at Granite Links in Quincy, and we had two or three tables of high school friends there. All of our closest friends now are friends from there, and some of them are also high school sweethearts.

OK: Ruby and Shayna, you’re next.

Ruby: Well, meeting and dating are very different. Our meetings started in pre-kindergarten. Right? We were the first class in a day school in Sharon that our parents had helped start. We went our separate ways for a little while, but we had crossed paths socially a little bit here and there. 

And then senior year of high school, we started just hanging out a lot. We had a pretty regular routine of going to Dunkin’ Donuts in the morning and getting breakfast. We were pretty close friends at that point. 

Second-half of senior year, Shayna came over and we acknowledged that it was more than breakfast buddies. Our technical first date was to Filene’s in the Chestnut Hill Mall, and we got Shayna perfume. It’s the same perfume she’s been wearing our entire 18-and-a-half years of marriage.

What perfume?

Hanae Mori.

What drew you to each other?

Ruby: We had a very tight-knit grade. Everyone was pretty close. So everyone had a lot of different friendships across the grade. We just kind of struck up this natural friendship that way, and one thing led to another.

Talia: I have a vivid memory of being in 10th grade when Ruby and Shayna were in 12th grade, sitting on the bleachers in the gym next to Shayna. And she says to me: “Who are the boys in 12th grade that you and your friends think are cool or attractive? What do you guys think of Ruby?” This was before they started dating. I vividly remember something was about to happen.

Did you break up before you got married?

Ruby: We were together until we got married. We went to two years of gap year post high school and dated through that, which is an impressive feat in and of itself. Then we were both at Yeshiva University. They have different campuses for the men’s school and the women’s school. We did it through that. Halfway through, we got engaged. We got married in college. That was a fun discussion with my parents, specifically my dad.

What was your take on that, Debby? 

Debby: We said: “Absolutely not.” They said they were doing it with us or without us. So we got on board.

Ruby: I put a very small downpayment on a very small diamond somewhere in midtown Manhattan. That was just kind of a statement to my parents. My parents said, “Why would you do that?” And I said, “It’s obvious why I would do that!” And they said, “Well, we have a diamond.” I said, “When were you gonna tell me?”

What makes a relationship last?

Ruby: I remember [a friend] was describing how people would talk about her parents’ relationship and compromise, and the mother said: “It’s never compromise. I’ve never compromised in my marriage once,” she said, “because we love each other so much, it’s what we want to do. What’s best for us and what’s best for each other is really what we want to do for each other.”

There’s been plenty of growth and discomfort through 22-plus years of a relationship, but it never felt like it was taking away from me personally. 

I think we also come from two very loving families, which makes it a lot easier for us to feel confident and comfortable in being hopeful and positive and loyal that way.

Do you have kids?

Ruby: We have four kids. The oldest was born during my senior week of finals in college. None of them are dating right now!

OK, Talia and Gaby.

Talia: Gaby has an interesting take. I can correct his version of our story.

Gaby: We met on the first day of ninth grade when Talia started at Maimonides. She was good friends with my best friend at the time, and he introduced us. Then, he dated her for a while after that. Fast forward: They broke up. And then a while later, I realized I liked her. We were very good friends. And she said that she did not like me. 

Talia: It wasn’t like “I don’t like you!” It was gentle.

Gaby: Is it ever really gentle? Anyway, later, there was a situation where somebody told Talia that I still liked her. A year or so later. 

Talia: In the process, we became best friends that year. This was now the beginning of junior year.

Gaby: So, somebody told her that I still liked her. And she was like: “No, that’s not true.” So she came up to me and said: “Do you still like me?” And when she asked that, I thought: “Oh my god, she finally likes me!” And she says, “Oh.” And that was that.

Talia: I remember a little bit differently. He has been retelling his version of the story for 21 years! 

Gaby: What you actually did was just stabbed me in the heart!

Talia: After 21 years of marriage and two children later, you think he’d be over it, but that would be much to ask.

Gaby: What would the fun of that be?

Talia: I’m going to take over now. The next part of the story is more me coming to realize that I did like him.

It was my birthday junior year, and we had just all taken the SAT IIs that morning. It was a Sunday morning, and I had the whole grade over for a birthday-slash-SAT II-is-over celebration at my house. 

At some point. Gaby left the party to hang out with another girl. I got really upset. My best friend said, “If you don’t like him, why are you so upset?” I was like, “I’m a teenage girl. I don’t know what you want from me!”

It took another couple months for me to get jealous again. Then I knew: OK, fine. I definitely like him. I was at his house one night. We hung out a lot, so it wasn’t atypical. Basically I was like, “I have something to tell you.” Three hours later, I managed to get out the full sentence that I liked him. It was a slow process. 

At the end of the night, I was leaving his house in Newton. I was about to drive away, and I rolled down the window and said, “Gaby, you know that means we’re going out now, right?” He was like, “OK.” 

That was February 19, 2001.

We did long-distance and dated until he graduated college. I graduated a year before him because I didn’t go to Israel. The first Sunday after graduation, we got married, in June 2006.

Do you all hang out a lot as a family?

Talia: The boys, when they get together, half of it is quoting movies that they watched when they were in high school and middle school and laughing about it. 

We’re all very close. And the cousins are really close.

Debby: My husband and I always say one of our favorite things when all the kids are together is being in bed late at night and listening to all of them laughing and having fun together into the night downstairs.

Debby, I’m going to put you on the spot. You must love all you must like all of your daughters-in-law, right?

Debby: I feel very, very blessed, and I feel that they are the right people for my sons. We just feel blessed that my sons chose the wonderful women that they did and that all the couples know how to be good spouses and loving husbands, wives and parents. 

One of the things that I want to say also is that the advantage of having the boys marry high school sweethearts is that, because I had all the years of having the girls in and out of the house and coming from the same area, we knew their parents. That was really a very nice thing for us. Having them come into the family was just very natural. 

Do you have any other kids who aren’t married to their high school sweethearts?

Debby: No. It’s three for three.

Wives, any common trait for all the brothers?

Everyone: Charmingly immature. And charming.

Shayna: They’re all very loyal.

Talia: They all have good taste in women.