His limited experience gives him a leg-up on reading social signals, picking up dating cues which would give him confidence to date.
With some of these suggestions, you're sure to have a leg-up on preparing and enjoying (and getting through!) the holidays.
Numerous free business letter samples are available online to help would-be writers get a leg-up on where to start.
Perhaps, this is the leg-up that Nintendo needs to grab a huge market share.
That can give the person the leg-up needed to write about them.