$100 is an interesting price point. It seems like anytime my husband I go out for a sit down dinner, 2 entrees + 2 cocktails + tax/tip and we're at ~$40-50. These are the meals I could cut out with no real qualms, and sometimes do for months at a time - they often seem good but not worth the money. Plus at brew pub type places, I could make most of that stuff at home, and have.
We spent right around $100 last Friday at the supposedly best restaurant in this quaint little destination town nearby. Worst meal I've had in a long time. Just terrible - overcooked, over-seasoned, bland, ugh. My husband had a plate with a small filet, a piece of chicken, and a tuna steak, all of which tasted like bad Thanksgiving turkey leftovers. Total regret.
My favorite (and arguably the actual best) restaurant in town does a 10 course tasting with wine pairings that works out to $400 for 2. Some of the most amazing bits of food I've ever had in my whole life - fresh, creative, beautiful, delicious, just an all around awesome experience. I've been doing that for my birthday every year, since the years I had to scrimp and save to make it happen. It's been great. We dine at that level like twice a year - our anniversary, and his birthday. These are awesome, special evenings and I'd hate to have to give them up.
We went out last night to a Mexican place where the only thing on the menu is chicken - a whole, or a half. Half a charbroiled chicken, stack of soft tortillas, beans, rice, and a full sugar coke for like $9. It's dive-y and delicious, and probably one of my favorite cost-to-awesome ratio discoveries.