How Much is Too Much for a Dream Dinner?

I am obsessed with food. I am. I love dining. I love chefs. I love interesting and different food (lets not go crazy, I'll pass on most offal). I want to eat in ALL of the best restaurants and taste the delights that a skilled chef can create. But, lets face it, I'm on an Olive Garden budget. I like to THINK I can just eat whatever and whenever and wherever I want, but if I eat at all of the places I want to, I might just break my bank.

So, what's a girl to do?  Where is the limit?  I have no problem spending $125 for two for dinner.  It's a splurge, but we do it on occasion.  But what about when I get the chance to eat at some of my dream restaurants?  Lets say I was going to New York.  Now New York is a place where I just won't be going very often, so when I do get there, I want to experience as much as possible and no matter how many amazing restaurants are around the world and in my own backyard, the truth is that NYC is a gourmet dining capital.  How do I pass this up?

One of my dream restaurants is Daniel.  While Daniel is no longer at the top of the top in NYC, it is still a classic fine dining restaurant with amazing seasonal menus that are crafted with care. Daniel may have a lot more competitions, but it's somewhere I have long dreamed of enjoying the seasonal tasting menu.  The problem?  The "cheap seats" on that tasting menu is STILL $195 per person and that doesn't even include the wine pairings.  Yeah, I said $195 per person!!!  

That is only the tip of the iceberg.  What about my fantasy of eating omakase at the hands of Mr. Uezu at Kurumazushi.  Take a guess... go ahead.  Omakase STARTS at $300 per person.  But this man is known to be a master with seafood that he has flown in for his restaurant.  Can anything be worth that much?  I know you can get meals much more expensive, but these are just my simple little dreams.

Chefs Table at Brooklyn Fare is another fantasy.  This one isn't even in reach because besides the $225 per person price tag, it's dinner only and there is much raw taking place, which my husband would not be interested in.  I can't exactly ditch him for dinner!  So, even if i could get a reservation... this one truly is out of reach.

You can see the problem.  There are more...  There's Blanca, and Jean George, and there's Per Se and Le Cirque, there's Momofuko and another long time New York icon Le Bernardin.  I mean, New York City is an eater's paradise.  

So here is my question.  When do I pass from "but it's a special occasion" to "I seriously need to commit myself before I bankrupt my family"?  How far is too far for this middle class girl with a middle class credit card and a middle class husband.  Do I do Daniel and go cheap the rest of the week.  Do I pick a few of these splurges as "one of a kind nights"... and then where do I draw the line?  $200pp?  $300pp?  How do I pick a limit?  HOW MUCH IS TOO MUCH?