@fluffy in this case, I would definitely go easy the first time. Play how any Joe schmo would. Still beat her, but don't use any advanced tech.

Thinking in terms of like, Mario Kart, since I know that more than chess, I'd probably not just immediately jump to 200cc and kick her ass. Unless she was shit talking and saying she would definitely beat me. Put it on 100cc and tell her to use the steering assist or something.