A "cheeky message" refers to a lighthearted or slightly mischievous message that is intended to be playful, funny, or flirty. It often conveys a sense of fun and playfulness. Full definition
Send cheeky messages to people you find attractive and those that you have plenty in common with, and see where innocent conversations take you. (officialdatingguide.com)
No amount of sexy selfies on Instagram, cheeky messages on Tinder or likes and shares you give and get can replace the power of dating in the offline world because that's where all the real action happens. (loveprofileexpert.com)
And we brainstormed fun new product concepts that would get people talking, like our «Breakup Gift set» that features candies with cheeky messages like «Stop Kissing Frogs» (gummy frogs) and «Plenty of Fish in the Sea» (Swedish fish). (theeverygirl.com)