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Where to take an older, hard-boiled, eccentric but loveable drinker?

Swankalicious | Oct 28, 201105:21 PM

My bachelor uncle is coming up from Manhattan. In a nutshell: The guy has lived in the same rent-controlled studio apartment for 40 years, is a huge packrat, smokes two packs a day, and is extremely eccentric and curmudgeonly (yet fun, with tons of great stories). He's coming up to Boston to meet a woman he met online (yes, this is 2011!) and we're meeting the night before for drinks and dinner.
The guy likes to drink. He's definitely an old-school bar type. I'd like to take him someplace for a few stiff cocktails and then a good steak dinner (he's not a very adventurous eater).
Any suggestions are welcome. He's staying in Cambridge, but I have a car and can pick him up and go wherever.

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