The two women introduced their boyfriends, Machine Gun Kelly and Travis Barker, at the MTV VMAs, and made a remark that fans had a lot to say about.
The "KUWTK" star and Blink-182 drummer officially confirmed they were dating in February.
After reports emerged that Jenner was having a second child with on-again, off-again boyfriend Travis Scott, she confirmed the news on Instagram this week.
The couple's 18-year age gap was the subject of much discussion among fans and Hamlin's own mother, "Real Housewives" star Lisa Rinna.
Disick apparently attempted to commiserate with another of Kardashian's exes about her PDA-heavy new relationship with Travis Barker, and it majorly backfired.
The 24-year-old billionaire is already a mom to daughter Stormi Webster with rapper Travis Scott.
But her big sister Kourtney Kardashian said her memory differed.
The reality star addressed reports that she's back together with her ex by rebuking a critic who said she had "no self worth."
The couple hit a PDA TKO in May when fans found footage of the Blink-182 drummer sucking her fingers at another UFC fight.
Tristan Thompson lashed out at Kardashian's ex-husband, Lamar Odom, over a flirty comment on her recent Instagram pic.