1. Liberty Hotel
Some people find God in prison, but you're just looking for a date. Drop in on The Liberty, housed in the rehabbed former Charles St. Jail building, on a Thursday or Friday and you'll find two bars (Alibi, Clink), one upscale Italian restaurant (Scampo) and a trendy, older crowd of gorgeous women sipping cocktails and generally looking good. If you can't find someone here, maybe you deserve to be locked up.
215 Charles St., Beacon Hill (617-224-4000).