Your Best Free Drink Story, Please, Straight Up

Or is there no such thing as a free drink?

Ester Bloom
The Billfold
2 min readJan 29, 2016

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Master of None

Part of what you miss out on when you get coupled up at 18, and then end up staying that way forever and ever amen, is dating and specifically free drinks. I’ve never been 1) of legal drinking age and 2) single at the same time. That’s incredible.

The whole bar scene seems like a rite of passage I’ve missed out on. Like, consider: Buzzfeed’s #1 tip for stretching your money until payday is flirting for free drinks. I read that in total bewilderment. Is it something people actually do? How does it work? Are there people who always buy drinks and people who always receive them, or do folks take turns? And what do you owe the person who sends a shot your way?

I’ve had so few cocktails bought for me in my life as an uncool person that I can remember each one. A couple of highlights:

  • At my 10-year high school reunion. One of my best friends from those days was there: I’d been in love with him then, while he obsessed over the only other girl in the whole school who had my name. He took me to senior prom and spent the whole time watching her. Maybe he offered the whiskey and soda as reparations.
  • At an off-season beachside bar in the Far Rockaways. The fact that I was there with a lesbian couple didn’t deter the old man on the stool. Neither did the fact that I was wearing a wedding ring. He insisted on paying for my mojito even though I’d done nothing but smile awkwardly at his attempts at small talk. Afterwards I wondered what my obligation was: smile again, say thanks, and run, or did I owe him more than that? I opted to smile, thanks, and run.

Please share your memorable bar stories and let me live vicariously through you! Have you ever bought someone a drink and gotten way more, or way less, than you expected? Or been bought a drink and been flattened and flummoxed by the consequences? What have you decided, over the years, that a cocktail is truly worth?

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Ester Bloom
The Billfold

Senior Editor, CNBC; former editor @thebillfold; contributing writer @theAtlantic