press (one's) luck(redirected from press his luck)
press (one's) luck
1. To risk losing the success or fortune one has garnered thus far by brashly or overconfidently seeking more. I've had some good winnings at blackjack, but I don't think I should press my luck any further.
2. To try to gain some additional benefit or advantage after one has already been granted or awarded something. Usually used in negative constructions as an imperative. If Mom is letting you stay out till midnight on Friday, don't press your luck and ask for a later curfew on Saturday, too. A: "Thank you for the raise. I was wondering if you might also consider expanding my benefits, too." B: "Don't press your luck."