“The good part of having six kids is, there’s always one who wants to hug you and say, Daddy, I love you,” John McEnroe wrote in his autobiography You Cannot Be Serious. This softer side of McEnroe contrasts with his fiery on-court persona, showcasing a loving father who prioritizes family. The American legend divorced his first wife, Tatum O’Neal, in 1994, but his relationship with his children, including daughter Emily, remained unaffected. McEnroe’s affection for Emily has always been evident in his words and actions; this time, it’s no different.

From his first marriage to O’Neal, McEnroe has three children: Kevin, Sean, and Emily, while with his second wife, Patty Smyth, he has two daughters: Anna and Ava. Additionally, he is also a stepfather to Patty Smyth’s daughter, Ruby, from a previous relationship, making him a parent to six children in total! So, even when he’s not commentating on tennis, John has certainly got his hands full keeping up with all their lives.

Excitingly, his eldest daughter, Emily McEnroe, who took after her mother to become an actress and even appeared on the big screen for the movie Futra Days in 2024 alongside Roanna Arquette and Tania Raymonde, posted a fun update to her Instagram account. She shared a picture showing off the sparkling ring on her finger with the caption: “forever & a day @timothyjmass 💒” Yes, you guessed it right! She just got engaged to her boyfriend, Timothy, and she updated her followers with a heartwarming photo montage, including John in one of the pictures!

Standing alongside Emily and John, Timothy ironically wore a t-shirt reading ‘McEnroe said it better,’ as the three were all smiles.

This comes shortly after McEnroe’s other daughter, Anna, tied the knot with her partner, Brian Kerrigan, on October 5, 2024. The wedding was a joyous occasion, with John in attendance. He had stepped down as captain of Team World at the Laver Cup just days before. In a heartfelt moment, he promised Anna that he would “win” at her wedding, contrasting the loss he experienced at the Laver Cup. Anna’s sister, Emily, shared heartfelt photos and messages on social media, capturing the love and unity of the McEnroe family on this special day.

And, well, Emily’s brother Kevin is getting married this year as well! Tatum spoke of it during an interview with Variety Magazine this month, excited to attend the ceremony in June. However, this also marks the first time that John and Tatum will be in close quarters after splitting three decades ago. While many expected the atmosphere to be awkward, considering their dramatic divorce, Tatum stated that “The anger is gone.”

The McEnroe family is set for a double celebration. This means we can expect not one but two family reunions soon! The last time John was spotted with Emily was at the Indian Wells Tennis Garden, where he jammed on his electric guitar alongside his band.

Emily encountered an awkward moment during the 2024 Indian Wells Open

Last year, John McEnroe and his daughter, Emily, stole the show at the Indian Wells Tennis Garden with a musical performance. She took to Instagram to share snippets of their gig, where she sang lead vocals while John showcased his skills with the guitar. In one hilarious moment, a fan asked for her autograph, only to jokingly admit they’d rather have John’s signature. Emily humorously recounted this on Instagram, saying, “Thank you to the woman who asked for my autograph I said ‘are you sure?’ she said ‘well, I’d rather have your dad’s.'”

It’s not the first time Emily has faced scrutiny because of her parents’ status. As the daughter of a seven-time Grand Slam champion and an Academy Award-winning actress, Emily often faces accusations of nepotism. However, she’s quick to set the record straight. In a candid Instagram story last year, she addressed it, saying, “Let’s talk about the obvious. There’s an issue with nepotism. Oh, everything was handed to you on a silver platter, on a gold platter. Oh! Well, so far, basically, no, it hasn’t, okay? It’s like I’m a famous person without the perks. I’m like a famous person who can’t get a dinner reservation. What the hell is that about? I just want to work.”

Over time, Emily has carved her own path in Hollywood, making her acting debut last year. She also worked as Scarlett Johansson’s voice double for Ghost in the Shell.

We might not see another father-daughter performance at the Indian Wells Open this year, however, there’s still plenty to look forward to for the family.