Planning a romantic night out? Here’s some essential insider tips straight from behind the bar.

Of the many legends touted as the origin story for Valentine’s Day, historians can at least agree that the celebration is borne out of some occasion that brought together strangers in the spirit of love. That means we have a reason to meet—a date, perhaps—and a reason to celebrate—to eat and to drink (as if we needed a reason).

Valentine’s Day can take the form of a memorable first date, a traditional night out with significant others, or a night of galvanized bachelorhood for those wishing to protest. The stakes are high! That is to say that sentimental gestures, on February 14th especially, run the risk of being overly sentimental, awkward, and downright tacky.

To avoid a potential flop, heed the advice of those who make put great thought into curating such an occasion, and who forego their own plans so that you can enjoy theirs: your servers and bartenders.

Seasoned industry folks have seen it all: the igniting of a spark between strangers, the crash and burn, and everything in between. I sat down with Will, a veteran Boston-area bartender, to get a sense of some dos and don’ts from across the counter:

Do indulge in whatever specials might be up for grabs at locations around town.

There’s no shortage of restaurants in the area that are offering deals and special menus that befit the occasion. Will’s a big fan of the “Valentine’s cocktail, made for two. It gives [couples] something to share.”

Don’t think that special menu items are automatically a cliché.

While bars and restaurants have to accommodate a wide array of tastes, they wouldn’t put something on a menu that they couldn’t stand behind. “Think of it with this analogy,” Will says, “every year, Christmas happens, and things are marketed for Christmas. Whatever’s on the menu [for Christmas], the business supports it.” and wants you to buy it! “Why wouldn’t you want to capitalize on an event?”

Do plan a night that you’ll truly enjoy.

Maybe you want to spend the evening ogling at your partner across a white table cloth. But grand displays of affection might not be everyone. You can still use Valentine’s Day as an excuse to “find groups of people who are hanging out that night, and just hang!” Regardless of how you participate, it’s always “a particularly fun and busy night—sparkling really.” (There’s even a few places hosting anti-Valentine’s Day events).

Don’t aim to impress just for the sake of being flashy.

Citing far too many of these experiences, Will urges patrons: “don’t order the most expensive bottle just because you want to look cool. They’re that expensive for a reason, but if you can’t appreciate that, don’t go there.” Your evening should be about you and the person you’re with, not about what people see you doing. (On that note, do you really want to propose on Valentine’s Day?)

Above all else, keep in mind that a successful night out on Valentine’s Day can be very, very simple. Let the employees of your restaurant of choice tailor the night for you; take that stress off yourself. From there, Will boils success down to two principles: “Show up. Do that part.” Aside from that, “Do anything you would do on a normal date. It’s really like any other night but, of course, love is in the air everywhere.”

Eligible bachelors, happily married couples, anti-Valentine’s Day protesters alike have plenty of options for February 14th. And, if you need a suggestion from someone in the know, “find a place to go to dinner. Maybe start with a cocktail, move along to a bottle of wine, some food of finer quality. Then, go for a little stroll.”

If you’re looking for a little more flair, Will says, “I’ll be celebrating by setting cocktails on fire.”

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