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‘With Love’ Season 2 is coming — Here’s everything we know

The romantic dramedy starring Emeraude Toubia and Mark Indelicato returns for a second season this June.
With Love Season 2 - First Look
Mark Indelicato (Jorge Diaz Jr.), Isis King (Sol Perez), Vincent Rodriguez (Henry), Desmond Chiam (Nick Zhao), Emeraude Toubia (Lily Diaz) are ready for new adventures.Courtesy of Prime Video
/ Source: TODAY

This post contains spoilers for Season One of "With Love."

Get ready for more family, celebrations and mucho amor.

“With Love” returns for a second season in June and the Diaz family is cooking up some romance, drama and big surprises.

The series, created and executive produced by Gloria Calderón Kellett, followed Lily (Emeraude Toubia) and Jorge Diaz (Mark Indelicato), siblings who were navigating the highs and lows of love during the holidays. Each of its five episodes, centered around a holiday beginning with Nochebuena (Christmas Eve), followed by New Year's Eve, Valentine's Day, 4th of July and Día De Los Muertos (Day of the Dead).

It's been over a year since the Prime Video romantic dramedy debuted in December 2021.

The first trailer, release date and peak at what the Diaz family is up to dropped in May, promising even more romance, love triangles, heartbreak — and a possible wedding?

How did Season 1 of ‘With Love’ end? Here’s a recap

It was one full year of seeing Lily newly single, having fun with her brother’s best friend Nick (Desmond Chiam) and falling in love with Santiago “Santi” (Rome Flynn).

Lily and Santi endured hiccups when it came to their thoughts on marriage and happy endings. But as Christmas came back around the two seemed to be on the up and up.

Are Lily and Santiago end game?
Are Lily and Santiago endgame?Kevin Estrada/Prime Video / Kevin Estrada/Prime Video

Introducing Jorge's boyfriend Henry (Vincent Rodriguez III) to his big family proved to be a success, as they fully embraced him. The couple also had their trials and tribulations with Henry learning that Jorge's love language includes grand gestures while he's more of a low-key guy. The couple moved to Los Angeles when Henry got a good work opportunity, but moved back when Jorge's dad, Jorge Diaz Sr (Benito Martinez), suffered a health issue and was hospitalized.

As for Sol (Isis King), we saw their budding relationship with Dr. Miles Murphy (Todd Grinnell). After making things official, Sol met Miles' child Charlie (Birdie Silverstein). And while Charlie didn't want much to do with Sol at first, the two quickly formed a bond.

At the end of the season, fans were left wondering who was going to get engaged on Christmas Eve. After grandma Marta (Renée Victor) found a box with a ring in it, she, Beatriz (Constance Marie) and Tía Gladys (Calderón Kellett) looked to the young couples to see whose life would be changing.

Here’s what to expect from Season 2

The second season will consist of six episodes, with each one once again centering on a special event.

Lily’s life is about to get turned upside down after her whirlwind romance with Santi. According to the synopsis, “Lily will focus all her energy on a personal journey of self-love, by growing her makeup styling business and looking into homeownership.” She will then wrestle with what is best for her when both Santi and Nick profess their love for her. Who will she choose?

Will sparks fly between Lily and Nick?
Will sparks fly between Lily and Nick?Kevin Estrada/Prime Video / Kevin Estrada/Prime Video

Right when their relationship seems too good to be true, Jorge begins to question whether he and Henry are truly compatible. After meeting Henry’s “proud Texan parents,” Jorge “can’t decide whether the relationship is a fairy tale or a nightmare,” per the show’s description.

New characters will be in the mix

Calderón Kellett revealed in July 2022 that Busy Philipps and Cameron Esposito would guest star in the second season.

In the first look at Philipps’ role, the actor is seen at an outdoor game, sitting next to Miles and Sol. Not much is known about her character.

Todd Grinnell (Dr. Miles Murphy), Isis King (Sol Perez) and Busy Philipps in Season Two of "With Love."
Todd Grinnell (Dr. Miles Murphy), Isis King (Sol Perez) and Busy Philipps in Season Two of "With Love."Kevin Estrada/Prime Video / Kevin Estrada/Prime Video

Scott Evans, Chris Evans’ brother, will also appear as James, Henry’s childhood friend, Deadline reported. Adrian Gonzalez and Briana Cuoco (Kaley Cuoco’s sister) are also credited as new characters, per IMDB.

The trailer shows celebrations, confusion and familia

The first trailer, released on May 4, showcases the rollercoaster Season Two of “With Love” will be.

The two-minute preview shows Jorge kicking Lily out of his apartment and her reluctantly moving back in with her parents. Why might you ask? We’ll have to wait and see. There’s also flashes of a tearful and joyful Lily.

Then there’s Jorge realizing Henry’s parents are not what he expected. “I was so worried about Henry’s parents not liking me,” he says in the clip. “That it never occurred to me that I might not like them.” 

The new season could be just as Jorge describes:

“The emotional journey goes as follows: Shock and awe at arrival, dance your face off mid-party and then we end with that gut punch of will we ever find love like the Diaz family?”

When will ‘With Love’ Season 2 be released?

All six episodes of “With Love” Season Two premieres June 2 on Prime Video.