Addison is known for having the most restaurants per capita either in the US or West of New York or something like that. So... eat. Taste of Addison is about to kick off in a couple of weeks. Addison Improv is out there, too. I'm not sure there's too much more than that in the immediate area... like I said, it's known for restaurants and lots of them. The area is a bit similar to parts of Westheimer (or at least what I remember Westheimer to be... west of Chimney Rock, I guess - I have no idea what it's like out there now).
I live in addison at the moment, and although we dont go out here as much as we do in uptown, there's mainly bars and stuff. Blackfinn, Dukes, Sting and karma are ok. Depending on the scene, you might want to make the drive to uptown and check out all thats going on, as they have a better things to do.
If you like Cajun food Nate's is easily the best Cajun restaurant in the metroplex. If you want a Brazilian Steak House the Fogo de Chao is an all night affair and great food. If you are looking for something a little more romantic than try the Melting Pot, its fondu but really nice for the wife and really romantic if you are into that sort of thing. The Improv is there as well if you like comedy and there is a dueling piano bar that is close to the Improv as well. Outside of that, if you are looking for late night entertainment I would recommend getting out of Addison. If you don't mind a bit of a drive over to Fort Worth then the Stock Yards are a lot of fun. Lots of live music, lots of bars. If you like country and western stuff their are other places a lot closer like Red River. If you like the college scene and those types of clubs you can head down Greenville Avenue. You can also try out Deep Ellum on the east side of Downtown Dallas. Lots of live bands of all kinds. Hope that helps a little.
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If you're into Brazilian steakhouses/churrascarias, there are 3 within a few miles of one another. Just down the road from Fogo is Texas de Brazil and a couple of miles down the Tollway from there is Rafain. My fave is Rafain simply for the bang-for-the-buck value. I also love their spices. Texas de Brazil I've only tried 2 or 3 times and thought it was average. Fogo is great, but then you'll also pay for that. Given the choice, I'd still go to Rafain probably. I've always wanted to try Nate's but never have. Good cajun places around here are few and far between.
What he said... when i just want to hang close to home, I'll usually go to Blackfinn...lots of nice scenery... When i want to see hot chicks, I'll go to uptown, like Ocean Prime, ZaZa, etc... I also like Henderson area, near Ross/Greenville...The Park is good, barcadia, etc... If you want to be hunted by cougars, go to Sambuca 360 off Legacy... btw, Rafain's is the *****...For a good burger/scenery, go to Village Burger in west village...