The star was close with the Love Island host, who died in February 2020, and in her memory, Olly and some of Flack’s closest pals recently attempted to climb 24 peaks in 24 hours which Olly said was ‘special’ but also ‘really tough’.
However, opening up on losing his friend, who he presented The X Factor alongside, Olly questioned whether there was more that could have been done to help Flack.
Addressing the coverage of Flack’s court case over the alleged assault of her then-boyfriend Lewis Burton, Olly asked: ‘At the time, could we have all done more? Could we have all protected her more? I don’t know.’
He said: ‘Me and Caz has only seen, last two or three years, each other here and there, we were doing our own thing. I do question it all the time, could I have done more, could I have done this, could I have gone out?’
Appearing on Joe Wicks’ BBC podcast, Olly also spoke of how he was overcome with emotion after being asked to speak about Flack at a dinner with her friends following their recent climb.
He remembered: ‘There was times when we spoke about Caroline. There was times where we reminisced on stories because all of us knew her differently, and then we went out for dinner that night.
‘And, this completely threw me off guard, one of the girls who was with us got up and started talking and was saying thank you so much to everyone. And all of a sudden it all went round the table and everyone had to say something.
‘And I was so caught off guard, and they asked me to say something and I just couldn’t speak.
‘I just broke down and cried the whole time, in front of all these strangers that I don’t really know. And I was just like “what is going on?”‘
‘Grief is so tough and even now I don’t want to get emotional, but even now it’s really difficult to even think that we did a climb for someone that, in my eyes, is still here.’
He added: ‘Doesn’t make sense that she’s not here, it doesn’t compute yet. I’m still coming to terms with the idea she’s not here and that’s really weird.’
Having to compose himself as he continued to speak with Joe, Olly recalled Flack’s mother Christine messaging him and saying how proud she was of them for doing the challenge.
Olly admits the climb was tough both ‘physically and mentally’ but he can’t believe how well everyone did, with the climb raising tens of thousands for mental health charity Samaritans in Flack’s memory.
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