The reality star, 33, was at Olly's album launch in London, and the pair were seen getting very close, OK! magazine claims.
A source told the publication: "Olly was getting close to a trio of women at the party.
"And he was also cosying up with Jess.”
Olly's new album features collaborations with Ed Sheeran, Shaggy, Nile Rodgers and Snoop Dogg.
The report comes after The Sun revealed in April that Jess had split from Strictly Come Dancing professional Giovanni Pernice after five months of dating.
A source close to Gio said: “He was really into Jess and did want to make a go of it, but he struggled with the attention she gets and her popularity.
“They’ve tried to keep things amicable and told people they have both agreed to go their separate ways, but he was the one who first suggested things were going to end.
“She has been really upset by this. It’s a real shame but hopefully things will stay civil.”
Olly has been friends with Jess' brother Mark Wright for years, and the pair recently enjoyed a boozy night out together in Los Angeles.
And in 2017, Olly swore off dating Jessica – fearing he'd get told off by Mark.
He said: "Ahah listen me and Mark are good friends.
"I don't think I can date his sister it would be too hard I think.
"But she's lovely Jess we get on well, all of us get on well, but yeah you know…"
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