4 to 5 times dining out with the family at $25 per head: $400.
A latte for 2 at Starbucks every day + the occasional croissant: $400.
Sponsored lunch at work for 2 during the week at $7 per: $300.
With the remaining $1000, you still need to cover breakfast every day and evening dinner for a family of 4.
You don't need to eat out at a fancy place twice a day to get there at all.