A Gentleman's Guide to Theatregoing: The Eight Essential Shows For a Perfect Valentine's Day

News   A Gentleman's Guide to Theatregoing: The Eight Essential Shows For a Perfect Valentine's Day
Are you in love with a theatre lover? Is your sweetheart a stage door fanatic, but you don't know what that phrase means? Are you looking for Valentine's Day plans that go beyond a fixed-price dinner? Never fear; Playbill is here. With this guide to the best date spots in town, Cupid's arrow will aim right for your seats in the audience.



Still no plans for Valentine's Day? Hey, I get it. Every year it sneaks up, and suddenly you're responsible for having made dinner reservations a month ago, and every potential standard Valentine's gift has shot up to three times its regular price. There is, in our fair city, a solution to this annual problem, and it's right under your nose. Take her to the theatre, my friend. A gift that is experiential and mutually shared is perfect for a holiday that explicitly celebrates coupling up.

It can be a risky move. A good show will have enough of its own personality that she will think you carefully crafted this gift based on how well you know her, but the wrong show will work in exactly the opposite way. My father took my mother on a second date to go see the original production of Company on the heels of her divorce. It turns out a show contemplating the value of marriage was not the right move, and it almost blew up my dad's game. That said, they went on to have my sister and me, which speaks to the power of theatre as a perfect date even in less-than-perfect circumstances.

That said, fear not! I have meticulously studied the theatrical landscape on and around Valentine's Day this year, and it is exciting times out there. I've laid out just a few really great shows easily matched to your boo, no matter how singular she is.

For the history buff:
Hamilton at The Public Theater

There is a hip-hop musical about Alexander Hamilton and the creation of The Federalist Papers generating enormous vibrations downtown. Written by and starring Lin-Manuel Miranda, a Tony winner hip enough to be featured on College Humor, this show is being lauded as a game-changer for musical theatre in a great way. Truthfully, tickets are pretty hard to get, but it's worth a shot. Historically accurate and straight up dope as hell, your lady professor will swoon as she has a great time swaying her head to the beats and nerding out over the musicalization of one of the most interesting bios in the history of our country.

Daveed Diggs, Okieriete Onaodowan, Anthony Ramos and Lin-Manuel Miranda in <i>Hamilton</i>
Daveed Diggs, Okieriete Onaodowan, Anthony Ramos and Lin-Manuel Miranda in Hamilton Photo by Joan Marcus

Fill out the date: The restaurant at The Public, called The Library, is gorgeous, reasonably priced and just steps away from the show. Book a reservation in advance. If you're looking to make a whole day out of it, visit the Morris Jumel Mansion at 162nd Street. It was a headquarters for the Revolutionary War, and the some of the show was written there. Even just walking around the grounds is pretty wonderful.

Extra Boyfriend Points tip: If she's super in to this show, dig up the video of 21 Chump Street on YouTube. It's a musical adaptation by the same guy of a "This American Life" story — and let's not kid ourselves, if she's an academic and into theatre, there's no way she doesn't listen to "This American Life."

For the Bowie fan:
Hedwig and the Angry Inch at The Belasco

For my money, Hedwig is the only actual rock musical — you can unashamedly enjoy the music to this without ever having to use the word "showtunes." Hedwig, the story of a punk/glam singer whose botched sex-change results in what can only be called "angry inch," manages, even in this gussied-up-for-Broadway production, to defy every expectation of what a Broadway musical is supposed to feel like, and fills the Belasco with the screaming fans of the once-downtown drag sensation. The show is funny, filthy, intelligent and exciting to anyone who likes theatre, rock shows or drag.

John Cameron Mitchell
John Cameron Mitchell Photo by Joan Marcus

Fill out the date: Walk the extra couple of blocks West to 9th Ave., and voila, you're on Restaurant Row.

Extra Boyfriend Points tip: The show is currently starring John Cameron Mitchell, who co-created and originated the role. This is theatre history happening. It is easy to make the argument that Hedwig is one of the most important theatre pieces of the last 30 years, and to see it on the Broadway stage starring the legend who made it in the first place is a big deal. Make her feel special. She deserves to participate in history, don't you think?

For the hipster:
Uncharted 2015: Coming Out Concert! at Ars Nova

Ars Nova's emerging artists program, Uncharted, is the most consistent source of tomorrow's biggest artists. This year's Uncharted lineup is no exception. Every one of the artists being given a leg up this year in the Uncharted program is already accomplished and has unbearably cool projects in the pipeline. The Coming Out Concert is where you can see something from all of them before everybody hears about any of them. If your lady is the type to know what's got all the cool kids' attention, this is a must-go. The material presented will run the gamut of genres and styles, and it's guaranteed to be a blast — Ars Nova knows how to party.

Fill out the date: Ars Nova is all the way over by 10th Ave., so it'd be a waste not to wander over to the Hudson River. There's a nice little park on the water at 55th Street, if the weather is nice.

Extra Boyfriend Points tip: Ars Nova has a very cool lounge above the theatre. See what's going on up there. It's always worthwhile.


For the party girl:

At 11 PM on Thursdays, Fridays and Saturdays, the basement theatre at The Flea comes to life with a series of five brand-new short plays by NYC's hottest young playwrights. These writers are vying to get voted back to write the next episode of these bite-sized, often hilarious, serialized theatre experiments. Each ticket comes with your first PBR, and the room swells with a packed audience of great-looking young theatremakers. Blood packets are plentiful, the audience is raucous and nothing is sacred. This is THE downtown theatre party.

Fill out the date: As soon as you've voted for your favorite shows, book it out of the theatre and head to South's on Church Street. Get stools at the bar, order drinks from Jason (arguably the best bartender in Manhattan), and tell him it's your first time seeing #serials. He'll recommend some drinks and as the whole company fills in the bar around you, you'll have great real estate for the hottest after party in the downtown scene.

Extra Boyfriend Points tip: Just two blocks away is a 24-hour museum of odd items called Mmuseumm. You peer at the oddities through a plexi window cut out of a loading door, and call a number on your phone that will talk you through whatever catches your attention. She will melt at your coolness.


For the bookish type:
You on the Moors Now at HERE Arts Center

Jaclyn Backhaus' latest exploration in to literature is a must-see for anyone who loves 19th-century lit or weird theatre. The show pulls from the pages of "Pride and Prejudice," "Jane Eyre," "Wuthering Heights" and "Little Women" and is an examination of courtship and romance through the cultural lenses of classic literature and contemporary life. This show will appeal to the most intellectual parts of your lady as well as the visceral — Backhaus has never written anything that wasn't immensely smart and also accessible, and the director, John Kurzynowski sews together beautiful, immensely watchable stage pictures. Even if it's not your bag, you'll definitely be able to lean back, look at and listen to something pretty for a little while. Your lady will be weak in the knees as she pushes her glasses up the bridge of her nose.

Fill out the date: There's a charming little Mexican place across the park called Lupe's. If Mexican isn't your thing, you're just outside SoHo. It's hard to go wrong walking around and getting a little lost where the city falls out of the grid.

Extra Boyfriend Points tip: Buy her a nice copy of a Bronte/Austen/what have you biography, and give that to her (inscribed — always inscribe a gifted book) with the tickets acting as a bookmark.


For the lady who wishes she took in more culture:
Constellations with Jake Gyllenhaal

If she doesn't see a lot of theatre, but wishes she saw more, this show is right on the money. A lovely, simple, smart Broadway play that hits every necessary mark for a Broadway play. Great creative team, excellent cast — just a good, old-fashioned Broadway play. Celebrity star? Check. Arty-but-accessible direction? Check. Lofty-but-not-alienating ideas? Check. Catharsis? Check.

Jake Gyllenhaal and Ruth Wilson
Jake Gyllenhaal and Ruth Wilson Photo by Joan Marcus

Fill out the date: The show was supported in part by an Alfred P. Sloane science and art grant. Spend the first part of the day at The Hayden Planetarium for an adorable date, and then have a fresh perspective on an already wonderful day at the end of the play.

Extra Boyfriend Points tip: Talk about how likable Jake Gyllenhaal is. He really is, and your lady will love how unthreatened by him you are. Don't let her know the truth — all men feel inferior to Jake Gyllenhaal.

For the progressive, sex-positive, fun modern feminist:
Rock Bottom at Joe's Pub

Bridget Everett will rock your world in this cabaret. You and your lady will be shocked, thrilled, horrified, and delighted by the lengths to which Everett goes to entertain and inform. She's equal parts Oscar Wilde and Siouxsie Sioux, and her show is body-positive and affirming in every way. You and your partner will be screaming with joy before it's over. Also, there's plenty of nudity, which isn't a bad idea on Feb. 14.


Fill out the date: Joe's Pub has a great menu, so this date can be totally self-contained. If you're looking for more to do in the area, you're mighty close to Veselka, the famed 24-hour pierogi joint on 2nd Ave, or Crif Dogs, the hot dog spot on St. Mark's with the worst-kept-secret speakeasy you enter through the phone booth. If by some chance she didn't know about the speakeasy, you'll look like a damn secret agent.

Extra Boyfriend Points tip: Muse about the history of affluent New York by standing on the steps at The Public and looking across the street at what used to be the Astor Mansion — The Public was the Astor Library, and it was connected by an underground tunnel to the mansion (later cut through to make room for the NRQ line).

For the sincere, funny, love-of-your-life:
Rebecca and Evan: Your Love, Our Musical at The PIT

Full disclosure: I am the artistic director for this venue, so I have a vested interest in your coming to see this show. That said, I brought this show to The PIT because I believe it to be one of the best shows in town. Rebecca Vigil and Evan Kaufman, two of New York's top musical improvisers, interview an unsuspecting couple in the audience about how they met, what they like/dislike about each other, and so forth. After 15ish hilarious minutes (they are truly gifted at crowd work), the two of them present a brand new, fully improvised musical about that couple's love story. It's a super-fun alternative to traditional theatre, and it'll get you culture points as well as fun-night-out points. If your lady likes comedy, musicals, or just being in love, this show was designed for her. If you're worried about the reputation improv has, take my word for this one: I've seen this show bunches of times, and I have never seen even one person anything close to dissatisfied. If you go on Valentine's Day proper, you'll be treated to a full improvisational band, made up of the biggest names in musical improv.


Fill out the date: The PIT is just off of Madison Square Park, one of the most cared-for parks in the city. Be sure to take a stroll through on your way in or out of the show. Take some time to marvel at the Flatiron building like a tourist, and on the other side, at 25th and 3rd, there's a little hotel called the Carlton Arms, where every room, hallway, bathroom and staircase has been painted or decorated by an established artist. Take a half hour to walk around inside and marvel.

Extra boyfriend points tip: If she falls for the very handsome, very talented Evan (of Rebecca and Evan), stick around for another hour and you can see him in the runaway hit hip-hop improv show North Coast immediately afterward in the Underground theatre at The PIT.

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