Slideshow: Where to Take a Date to Drink: 5 Romantic Spots for Cocktails in Boston

Deep Ellum
Deep Ellum
Arguably my favorite spot to drink both cocktails and beer in Boston, Deep Ellum sets a high bar for quality and service. Co-owner Max Toste thinks bright light is anathema to a good drinking experience and the upshot is a decidedly romantic space to quaff.

Deep Ellum: 477 Cambridge Street Allston, MA 02135 (map) 617-787-2337;deepellum-boston.com

The Western Passage at Deep Ellum
The Western Passage at Deep Ellum
I asked Deep Ellum co-owner Max Toste about the inspiration for his Western Passage ($10), a unique blend of Batavia Arrack, Sweet and Dry Dolin Vermouth, Yellow Chartreuse, and house-made aromatic and orange bitters. Turns out he was frustrated with the common practice of treating Batavia Arrack like rum (it is distilled from sugar cane) and dousing it with so much fruit juice. Here he bucks that trend with a Manhattan approach that's faintly sweet, herbal, and incredibly smooth. Also the name evokes images of exploration, which is totally romantic.
Brick and Mortar
Brick and Mortar
They may not have a sign on the door, but there's plenty of brick and mortar inside this undeniably sexy Cambridge drink stop. Baseboard lighting illuminates bare brick walls (and little else) while the large, curved copper bar glistens invitingly. The space used to be a lounge called the Enormous Room, which was ironic (it's a small space) and silly, now it's called Brick and Mortar which is honest and smart.

Brick and Mortar: 567 Massachusetts Avenue, Cambridge, MA 02139 (map) 617-491-5599

Citizen Public House & Oyster Bar
Citizen Public House & Oyster Bar
At Citizen Public House you can have a suckling pig cooked for you and 7 of your closest friends, slosh your way through an enormous selection of whiskeys from around the world, and get wine and Fernet Branca on tap. The date-friendly space makes equal and effective use of leather, dark wood, and low lighting.

Citizen Public House & Oyster Bar: 1310 Boylston St Boston, MA 02215 (map) 617-450-9000;citizenpub.com

Very Old Cow at Citizen Public House & Oyster Bar
Very Old Cow at Citizen Public House & Oyster Bar
The terribly named Very Old Cow ($10) is a stirred mixture of Mezcal Vida, Aperol, Punt e Mes, Maraschino, and Peychaud's bitters. Is there anything more romantic than the image of hearts (of agave) buried among smoldering coals in the Mexican dessert? The Aperol and Maraschino offer fruit and sweetness to balance the smoky mezcal.
Eastern Standard
Eastern Standard
A Boston quality-cocktail stalwart, Eastern Standard impresses with vaulted ceilings, well-dressed barkeeps, and an understated turn-of-the-century-esque grandeur that makes drinkers and diners feel a bit special.

Eastern Standard: 528 Commonwealth Ave, Boston, MA (map) 617-532-9100;easternstandardboston.com

First Printer
First Printer
You can't really discuss cocktails in Boston without mentioning local legend Brother Cleve. While he's got a great name, Godfather Cleve would be more descriptive of his role in this town's emergence as a first-class drinking destination. This summer he took over drink menu duties at First Printer in Harvard Square and the results are as expected: delicious.

First Printer: 15 Dunster St, Cambridge, MA (map) 617-497-0900;thefirstprinter.com

The Correspondent at First Printer
The Correspondent at First Printer
From the menu: "An adventurous cocktail from early mixologist "The Only William". A blend of Pierre Ferrand 1840 cognac, herbal Green Chartreuse and the rare Liqueur de Rose. (The Flowing Bowl, 1891)" Cleve is well-known for his scholarly approach to reviving centuries-old drink recipes. The Correspondent ($10) combines three seriously pedigreed spirits to warm, herbal effect. In my experience, a little rose liqueur goes a long way toward romance.