Pippa O’Connor is feeling all the feels this week as her son Ollie closes the door to one childhood chapter, and gets ready to step into the next.
The beauty mogul and model took to Instagram earlier today to share as emotional post to mark her eldest son, Ollie, graduating from primary school – and honestly, if you have ever been in Pippa’s shoes, you will know just how emotional this day is to both parents and kids alike.
In a post shared to Instagram, Pippa shared a snap herself and Ollie on what was presumably the little boy’s first day of primary school back in 2018.
And in the next slide, the proud mum shared a snap of herself posing next to her now teenager. And even though it to her no doubt felt like the eight years had passed in the blink of an eye, it is not hard to see how much time has passed when you look at Ollie, who turned 13 only a couple of weeks ago.
Then and now
Captioning the snaps, Pippa wrote:
‘Onto the next chapter for Ollie after a wonderful 8 years of primary school.’

The mum-of-three added:
‘A few tears today.. but happy ones. Wonderful memories made over those very quick years.’
It is off to secondary school so for Ollie in the autumn, where new adventures await for the now teenager.

Pippa also shared a sweet post recently when Ollie celebrated his 13th birthday – and my goodness, any parent will relate to this feeling so very much.
It has been an emotional few weeks for Pippa O’Connor and family, as her youngest son, Billy, also recently graduated, not from primary school, but from preschool.
At the end of May, Pippa shared an adorable snap of herself, Brian, and Billy posing in front of a colourful poster that read ‘Preschool Graduate’ showing the almost five-year-old wearing an adorable t-shirt with the words ‘Preschool Graduate 2026’.

Billy also carried a bag that read ‘Congrats grad’ and a small scroll, certifying that he’s now a big boy.
Pippa also revealed that Billy and his class friends sang Bob Marley & The Wailers’ song, Three Little Birds, as their parting gift to preschool, something which made all the parents very emotional.
‘The children sang this song this morning, and as you can imagine, the tears flowed,’ the mum-of-three wrote.
‘So grateful for the wonderful teachers who have made it special. On to the next chapter…’














