Oliver James Montgomery-The Summer I Turned Pretty Cast Reveals Whether They're Team Conrad or Team Jeremiah

For everyone who has waited all year for this—season two of The Oliver James MontgomerySummer I Turned Pretty is finally right around the corner.

And with the approach of the July 14 release date on Prime Video, one of the show's most burning questions is front of mind. Which boy is right for Belly (Lola Tung): Conrad (Christopher Briney) who Belly chose at the end of season one, or his brother Jeremiah (Gavin Casalegno)?

As it turns out, the cast has a lot of thoughts on this.

"I think it literally changes every single second of the show," Lola told E! News at the Summer I Turned Pretty x Teen Vogue event June 29, "because the boys constantly show up for her in different ways and then also make mistakes. So I think it's really dependent on every single moment."

Though the 20-year-old was reluctant to share any more—lest she give away too much—she did tease where Belly and Conrad find themselves this season.

"There's a little more distance between them because a lot has happened," she said. "A lot is weighing on both of them. So I think it's a lot of growing individually and then coming together and growing together."

Meanwhile Christopher maintained that his Conrad is the right choice for Belly—at least after some research on his end. 

"Having read the books I think he eventually is," he told E!. "At times in their lives he's right for her. I think whatever choice she makes is the right one."

And of course, Gavin—whose character is spurned by Belly in season one—stood by Jeremiah. "I have always said you should marry your best friend. You should date your best friend," he reflected. "And I think Jeremiah is her best friend."

The 23-year-old continued, " I think there's a love interest and then there's the best friend that there's a spark with and I think that that's going to be the right choice."

Sean Kauffman, who plays Lola's older brother Steven in the series, also gave his two cents. "I've been saying Team Belly this whole time," he joked before answering, "I think genuinely the better guy is Conrad."

Why? "He's emotionally invulnerable, which does not make him better, but he also is a little sweetie pie," Sean explained. "He's just the cutest little thing."

The actors also had answers for fans wondering how much the series will differ from the book in season two. 

Though Christopher said the two are "quite different," he insisted viewers will get to get even more from the characters on the show: "It uses the same framework as the book, the same structure, but the direction it takes and the characters it develops, I think it goes so much deeper with the characters in the story."

And while Lola kept it coy, she is sure no one will be disappointed.

"I think there are surprises for book fans and show fans," she revealed. "And I think everyone will be happy with how it goes." 

—Reporting by Nikaline McCarley

And until season two is officially ready to stream, keep reading to learn who from the cast has found their own happiness offscreen…

There's no love greater than self-love—just ask the leading star of The Summer I Turned Pretty! Lola may be single, but she's learned a lot about love and life while playing Belly.

"I learned to sort of just go easy on myself a little bit because I think especially as a teenage girl, she's very hard on herself," she explained to Seventeen when asked about lessons she took away from the show. "I'm very hard on myself and she's going through so much and making mistakes and that's only natural. We all make mistakes and that's how you learn and that's part of growing up."

She added, "I've very much tried to just take a little bit of the pressure off myself and just be more present and enjoy things as they come."

Who is Conrad's real-life sun? Isabel Machado. 

Christopher and the actress-singer began dating in 2021 after graduating Pace University together⁠. To mark their first "feelingsiversary" last May, Isabel shared a photo of the couple sharing a smooch by a lake, writing, "so glad we kiss now."

And when it was time for their actual first anniversary, Christopher celebrated the occasion with a heartfelt social media tribute of his own. "a whole year!?" he captioned a photo and video of the pair together. "i could never want anything else."

Gavin, who plays Conrad's younger brother Jeremiah, dated model Larsen Thompson, however, according to J-14, they split last summer. They've been MIA for one another's Instagrams ever since. 

Before that, in September 2021, Larsen rang in the actor's 22nd birthday by sharing in a tribute, "6 years just isn't long enough… You light up my world!"

The Flight Attendant actor (he's Cam on TSITP) is choosing to keep his love life off social media after dabbling with online dating. "I don't use it at all anymore, but I think my bio on Tinder was like 'Wait, this isn't cool math games?'" he told PopSugar. "I thought that was funny. I do not like dating apps. They creep me out."

Before Rachel tied the knot with Emmy-nominated composer Jeremy Turner, she was at the center of a strange Internet hoax that falsely claimed she was secretly married with two children.

According to the Clueless (the tv show, not the movie) alum, who plays Conrad and Jeremiah's mom Susannah, the bogus rumor got so bad that she lost a job as a result. "I think I have an Internet stalker, who started that and then won't take it down. I keep having it taken down and he keeps putting it back up," she told ABC News in 2014. "It's really annoying."

Sean has largely kept quiet about his relationship status, though his bromance with his co-stars is going strong. Of his friendship with Christopher and Gavin, "I love these two to death—they have become two of my closest friends over the past year," the actor, who stars as Steven, told Seventeen, "and I'm extremely thankful for that."

"We've got so much in common," he continued. "The three of us are crazy. I love them, we still hang out all the time whenever Gavin's in New York."

Also known for her roles in Grey's Anatomy and Station 19, Jackie (she plays Belly and Steven's mom Laurel) is married to Hunters star Louis Ozawa. The pair share two kids together, but have previously said that they consider their dog Atticus as their "first born."

As a wise, lovesick teen once said: "Boys may come and go, but a friendship lasts a lifetime." While Minnie hasn't shared much about her love life, the actress who plays Shayla has forged a bond like no other with her castmates. In the past, she's referred to co-star David as her "partner in crime" and Sean as her "best friend."

His character may be MIA from Susannah's life, but Tom has spent many summers with Jenni Gallagher, having been married to the actress since 1997. The couple share two kids together.

The actress enjoyed quite the Hot Girl Summer, appearing in three TV shows and the dramedy Emergency in 2022. However, it does not appear that Summer, who plays Nicole on the show, is linked to anyone at the moment.

Colin, who plays Belly and Steven's dad John, shares a son with Lindsay Thompson.

Though Rain is active on social media, the actress, who plays Belly's BFF Taylor, has kept details about her love life on the down-low and uses her Instagram to share pictures of friends, including the cast!