To be roguish is to be up to no good, which could mean being untrustworthy like a criminal or playful and mischievous. If someone gives you a roguish smile, he’s totally flirting with you.

You can't trust someone who acts roguish in the bad way, like the roguish crook who picks your pocket while telling you how lovely you look. On the other hand, you might like someone who acts roguish in the second sense, which means playfully mischievous. Being roguish in this way might mean playing pranks, telling racy jokes, and being a little wild. Roguish behavior like this can still be annoying, like if your roguish roommate at camp short-sheets your bed.

Definitions of roguish

adj lacking principles or scruples

“the captain was set adrift by his roguish crew”
blackguardly, rascally, scoundrelly
dishonest, dishonorable
deceptive or fraudulent; disposed to cheat or defraud or deceive

adj playful in an appealingly bold way

“a roguish grin”
devilish, rascally
full of fun and high spirits

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