


It’s ironic that an establishment so well-known for a long-running Sinatra brunch and Rat Pack-style aesthetic would wind up as a popular watering hole for millennials who probably think “Ol’ Blue Eyes” refers to Jake Gyllenhaal. Yet Lucky’s has been a swinging place to score long before Fort Point attained its newly attractive rep, luring after-work suits and Southie neighbors with live music that gets hips grinding and reasonable bar tabs that leave wallet wiggle room for morning-after Uber rides.
Lucky's Lounge
355 Congress St, Boston, MA 02210 • (617) 357-5825
https://luckyslounge.com
Other Winners
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Singles Scene—Under 30
2014 Winner: Brahmin
Don’t let the genteel name fool you...
- 33 Stanhope St., Boston
- (617) 723-3131
- thebrahmin.com
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Singles Scene—Under 30
2015 Winner: Lincoln
For upwardly mobile, fresh-faced South Boston transplants (the kind that make grizzled old townies shake a Guinness-grasping fist), there’s no better place to drop early-career paychecks and trade digits than at Lincoln’s two big, buzzing bars…...
- 425 W. Broadway, Boston
- (617) 765-8636
- lincolnsouthboston.com
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Singles Scene—Under 30
2016 Winner: Clerys
We mean it as a compliment when we say Clerys is a perfect stepping-stone for 20-somethings dipping their toes into the post-collegiate dating pool...
- 113 Dartmouth St., Boston
- (617) 262-9874
- clerysboston.com
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Singles Scene—Under 30
2017 Winner: Coppersmith
Set in a former copper fabrication plant, Coppersmith now manufactures good times for throngs of 20-somethings...
- 40 W. Third St., Boston
- (617) 658-3452
- coppersmithboston.com