Depends on what kind of gambling..
Well there's a wide Variety of things to do like:
Sports: probably the easiest imo, bet on who you think will win against someone else that opposes you. (Ex: NBA Playoffs going on right now)
Farming: Wager in on stipulations such as "Lowest dps/Death = Disqualified" on scrut, forcing you and your challengers to probably punch Cayus (grafu 1st boss) in the face doing strat, all kinds of chaos lol
Trivial: Grab a Challenger and put yourselves in party, Grab the first physical person you see (Example: New Player, first time playing, walking into Logar) generally someone you both may not know too well would be best to avoid favorability. ask him to ask you both a Trival Question about anything. The first person to say the correct answer according to the questioner, wins.
and a gamble wouldn't be a gamble without wagering big money so cap yourself on certain games to a risky level like in the millions margin, makes winning oh so much better. Of course that goes with having a respectful opponent that will accept defeat as much as you would.
Avoid playing hide and go seek with a rogue >.> I've had my fair share of con-artists in the day. Challenge yourself, play/make games that you, yourself would have just as equal shot of winning as much your opponent
lol hope some of that made sense and hope my suggestion would seem pretty entertaining/living on edge to you or anyone else reading