The 38-year-old singer - who worked with the late TV star on 'The X Factor' - has stayed in contact with her loved ones including her mother Christine and sister Jody after she tragically took her own life aged 40 on 15 February 2020.
Speaking to Jessie and Lennie Ware on the 'Table Manners' podcast, he said: "I do speak to Christine and Joe, like I saw Joe recently at the Choose Love event there was a shop opened, the shop was reopened in Carnaby Street and so I went and popped in and Joe was there, it was lovely to see her.
"And obviously, with her mom, I, you know, we randomly text each other here and there . If she sees me do something, or if I hear of something, I'll give her a little text."
The 'Dance With Me Tonight' star hailed his late friend as the "life and soul of the party", and he recalled the last time they tried to meet up before her death.
He said: "I just had my operation, 2019, And I said to Caz, I said 'I'd love for you to come and see me, I haven't seen you, I'm at home'. She's like 'I'm back from Love Island, I'll come and see you.' I was like... 'Okay, cool, what days good for you?' She goes 'Tuesday works great.' "
The pair arrange to meet at his home for lunch, and Olly - who was recovering from major knee surgery at the time - had booked a chef to come and make lunch for the two of them, while he let his partner Amelia know about the plans.
He continued: "And she never turned up. I was like, 'That's really weird because Caz didn't turn up', so I looked at my phone and texted her, I said, 'You alright Caz, I haven't heard from you, are you still coming?' She didn't text me back."
Hours later, she replied saying "something came up" and she wasn't "feeling great", suggesting they rearranged, while Amelia later showed him an online article revealing she'd been at a big party in London the night before.
He said: "It's a shame really, because I never got a chance to see Caz before. You know, she took her life. So it would have been lovely to have had a moment to chat or, you know, just talk. We didn't see each other for quite a few years. So it would have been, that was the last time we tried to meet up."
He added: "I always think back to that moment, I just wish you to come out to Essex that day."
Listen to the podcast here: https://www.tablemannerspodcast.com/
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