I'll throw in a few places outside for a possible Drive. In Irwin Area I like the following

Gato Taco -very good tequila selection, good frozen margarita's, and pretty good tacos

Laurel Highlands Meadery - Stop in here, walking distance from Gato and Burger Burger if you want a good burger but not date scene

Cenacola - locally made pasta and seasonal dishes. I like it, not crazy pricey but higher. Right next to Quinn brewing, which is great.

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Greensburg:

Olives and Peppers - Neat setting in an old train station, huge portions, decently priced. Wasn't my favorite chicken parm but it was good. They had a pistachio cheesey ball appetizer thing that was awesome.

The Headkeeper - Claims its a Tapas bar, but while they do Tapas portions, the prices are not, and they aren't typically shareable plates. But the food is really good I like sitting at the bar and watching them prepare dishes. It rotates quarterly. Great beer selection.

Bonus - White Rabbit Cafe, if your in the area early, I like stopping in here. Its a neat little cafe with a wide range of drink selections. They even have a horchata.

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Fayette County / Ohiopyle area

Out of the fire cafe - great date spot to sit outside on a nice evening. Expensive, but almost everything I've had there has been good. They even killed it with a Poke bowl.

Tree Tops restaurant - This is a neat experience type restaurant. I didn't do the tasting but sat outside in the fall. Great service and good food, but very expensive.

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Squirrel Hill area

I like Fujiya Ramen and noodlehead.

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Strip district / downtown

Gaucho - This one is already posted its pricey, but pretty good. Not always consistent though

Roland Seafood - I liked their lobster roll

Little bankok in the strip - Great pumpkin curry.