The Rejection Show
Littlefield, 622 Degraw St., nr. Fourth Ave., Gowanus; 8:00 p.m.
Anyone still feeling the sting of that last breakup can commiserate with like-minded souls here. Artists, writers, and comics will take the stage and share work that they've had rejected. The V-Day lineup will include Jon Friedman, Michelle Wolf, Aparna Nancherla, Eliot Glazer, Josh Gondelman, and more.
$10 advance, $12 day of show
Grandma's Ashes: We Won't Tell
Upright Citizens Brigade Theatre, 307 W. 26th St., nr. Eighth Ave., 212-366-9176; 10:30 p.m.
At UCB's Chelsea theater, you can tattle on an ex and feel empowered. Audience members will write down their secrets and the members of Grandma's Ashes will create a fully improvised show out of them.
$10
What I Did For Love
UCB East Village, 153 E. 3rd St., nr. Ave. A, 212-366-9231; 10 p.m.
Meanwhile, at UCB's downtown theater, comedians will be interviewing audience members about their love lives and turning the results into an improv performance. Love is a joke! Even if couples are there, they can be ignored.
$10
Annual Valentine's Day Planned Parenthood Benefit Concert & Dance
Music Hall of Williamsburg, 66 N. 6th St., nr. Wythe Ave., Williamsburg, 718-486-5400; 8:00 p.m.
Support a good cause while dancing the night away. The Jon Spencer Blues Explosion will headline, with local fave Jonathan Toubin of New York Night Train as the DJ. A plethora of special guests, including Lenny Kaye, Julianna Barwick, Cassie Ramone, Crocodiles, and EZTV, will also take the stage; plus, there will be raffles and dating games.
$20 advance, $25 day of show
Unloveable: A Smiths & Morrissey Valentine's Day
The Bell House, 149 7th St., nr. Second Ave., Gowanus, 718-643-6510; 9:00 p.m.
Looking to really lean into the loneliness of this holiday? Head to the Bell House and mope with host Rob Sheffield, the Sons & Heirs (a Smiths and Morrissey tribute band), the Steve McQueens (covering British pop group Prefab Sprout), and DJ Ceremony.
$14 advance, $18 day of show
Bad Suns, Coasts, Maudlin Strangers
Knitting Factory, 361 Metropolitan Ave., at Havemeyer St., Williamsburg, 347-529-6696; 9:00 p.m.
Check out some mellow indie rock at this low-key venue that's sure to be packed with beautiful young people, onstage and off. Headliner Bad Suns are having a bit of a moment, coming off a recent Jimmy Kimmel performance.
$15 advance, $20 day of show
Jeffrey Ross
Carolines on Broadway, 1626 Broadway, nr. 50th St., 212-757-4100; 7:30 p.m. and 10 p.m.
Ross is known as the "Roastmaster General" and is a regular on Comedy Central roasts, so expect some bitter, yet uproarious, comedy at this show, perfect for the slightly jaded among you. There are two sets, so you can start or end your night on a humorous note.
$71 show and dinner
Rosanne Cash
The Metropolitan Museum of Art, 1000 Fifth Ave., at 82nd St., 212-570-3949; 7:00 p.m.
For a quieter night with friends, check out Rosanne Cash at the Met. Nominated for three Grammys for her 2014 album The River & the Thread, Johnny's daughter is bringing her Americana-tinged tunes to this very special New York venue for one night only.
$75�$80
The Baldwins & Big Black Car
The PIT, Striker Stage, 123 E. 24th St., nr. Lexington Ave., 212-563-7488; 8:00 p.m.
More improv! And you won't need to worry about any awkward pauses here—these teams are veterans of the PIT and have it down to a science.
$10, $1 for students
Aesop Rock With Rob Sonic
Gramercy Theatre, 127 E. 23rd St., nr. Lexington Ave., 212-614-6932; 7:00 p.m.
Aesop's "ZZZ Top" was one of our favorite songs of 2012. He also, apparently, has the largest vocabulary in hip-hop. So, go learn a new word or two! The Bronx's own Rob Sonic will open.
$29