On the Rocks

puritan and co.Puritan & Co. bartender Colin Kiley sees it all from this very spot. Photo by Emily Hopkins.

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Puritan & Co. bartender Colin Kiley has seen a lot from behind the bar. Good dates, bad dates, blind dates—you name it, he’s gritted his teeth through it. Fortunately, he was willing to sit down with us to tell us what he’s seen—and share some of his wisdom.


Walking into the bar for a first date is basically like walking onto a stage, in your underwear, without knowing your lines.

“There’s the deer-in-the-headlights moment when people will walk in and just kind of look around. The lights hit them and it’s like, ‘Gotta make a decision, gotta make a decision, wherrrre are they?!’” says Kiley. The first thing you should know is that a little confidence goes a long way, even if you have to fake it. Kiley remembers one particular love story when woman fronted a “femme fatale” exterior and totally saved the date. This was still in the early-ish days of online dating, and Kiley says it could have gone so, so wrong.

“This guy’s sitting there waiting for his date, and his date gets there, and you could immediately tell that he … didn’t expect her to be as tall as she was or as curvaceous as she was. He was starting to get a little weird right off the bat,” says Kiley. But without hesitation, she put her best foot forward and got the date started.

“She was boss. Thirty-five, forty-five minutes into the date, he was a changed man.” They left together after two beers.


“I’ve seen some unmitigated disasters, for sure,” Kiley says. “There was this guy who was really, really into Call of Duty … I think she had done Peace Corps, or something like that. That was a one-beer date.”

Sometimes there are just no buts about it—the two of you aren’t meant to be, and you’re stuck on this date until the end of the meal. Never fear, your bartender is here.

“Someone might be on a roll talking, and the other person wants to kill themselves. That’s when they’re really, really hoping that you’re going to be there to pour that second glass of wine,” laughs Kiley.

“When you’re behind the bar, you’re essentially waiting for people to make eye contact with you to let [you] know that it’s okay to interrupt,” Kiley says. “People will steal just a second and look at you. It can be a funny little moment you can share.”


A bartender’s job is to be there when they’re needed and otherwise disappear, according to Kiley. Some people take that a little too literally. While most people would probably never admit to talking about such sensitive things in front of s stranger, Kiley says he’s heard some repulsive rhetoric. He didn’t elaborate, but he said that this especially comes up when people talk about family (yikes).

“A lot of people are surprised to learn just how many things you’re paying attention to,” Kiley says. “I hear everything you say.”


“That is definitely an occupational hazard, especially if you’ve been nice, if you’ve done your job well,” says Kiley. “You [the bartender] are the first thing they see, and if you don’t look so bad, you will get some phone numbers.”

This might seem like a classy move, and maybe it works in the movies. But in real life, leaving your number after you’ve just been on a date does not make you look like James Dean or a femme fatale.

“They may have just smooched the person, and you’ve kind of seen that, and then they’ll stop at the bar before leaving. These are the ones where you’re like, ‘Yeah, not interested in getting my face broken open.’”

Asked if he or someone he knows has ever taken the plunge into these murky waters, he said, “Without going into details or specifics, I would say most people could answer yes to that. And you quickly realize to never do it again.”