A Valentine’s Day to Remember

Cupid’s Undie Run is a fun, unique way to celebrate Valentine’s Day and support a good cause. Photo courtesy of Cupid’s Undie Run

Valentine’s Day is Saturday, conjuring images of red roses and Necco wafers with quirky messages. For many, the holiday also brings  pressure: coming up with a plan guaranteed to be a romantic hit.

Boston offers more than the standard candlelit dinner, candy, and flowers. From speed dating to dance parties to live performances and naked scavenger hunts (yes, you read that right), our guide to Valentine’s Day—broken into four categories—will get even the biggest cynics into the spirit of the holiday.

If you’re single and ready to mingle…

Netflirting: Instant Valentine’s Matchmaking at Lir Pub

Finding the perfect companion can seem next to impossible. That’s where the matchmakers at Scenergy Dating come in. They’ll be on hand Friday at Lir Pub for an evening of “instant matchmaking,” with professionally trained matchmakers helping those mid-20 to mid-40 connect and maybe even find love. The evening includes raffle prizes, one free drink, and discounted bar bites.

Netflirting: Instant Valentine’s Matchmaking is Friday, February 13, from 7 to 9 p.m. at Lir Pub, 903 Boylston St., Boston. Tickets (a free drink included) are $25 in advance, $35 at the door. Purchase tickets here. Take an MBTA Green Line trolley to the Hynes Convention Center, and it’s a short walk.

Plenty of OK Tinderfish Live: CrossFit Speed Dating at Commonwealth CrossFit

If you’re a fitness fanatic looking for your swolemate, this exercise-themed speed dating event just may be the Valentine’s weekend activity for you. Join fellow singles at Commonwealth CrossFit in Somerville for cocktails, conversation, and dating (no jumping jacks required).

Plenty of OK Tinderfish Live! Is Friday, February 13, from 8 to 10 p.m. at Commonwealth CrossFit, 630 Somerville Ave, Somerville. Tickets, for 21+, are $25; purchase here. Take an MBTA Green Line trolley to Park Street, switch to an outbound Red Line train, get off at Porter Square, and walk about a half-mile.

Cupid’s Undie Run

Showing up somewhere wearing nothing but underwear is the stuff of nightmares, but Cupid’s Undie Run is all about stripping down for a good cause. The proceeds benefit the Children’s Tumor Foundation, a nonprofit that funds research aimed at ending the genetic disorder neurofibromatosis. Underwear-clad runners will jog through Fenway Park and enjoy a party before and after at the Landsdowne Pub.

The Cupid’s Undie Run opening ceremony party is noon on Saturday, February 14, at the Landsowne Pub, 9 Landsdowne St., Boston. The run begins at 2 p.m., followed by a VIP bar event that ends at 3:30 p.m. The race entry fee is $55 and runners must register in advance here. Walk to Kenmore Square, turn onto Brookline Avenue, and take a left onto Landsdowne Street.

If you like the dark side of Valentine’s Day…

A Good Night for a Bad Date

Ever wondered if there was a reason you were single? Well, leave it to the brilliant minds at MIT to help answer the question. This MIT Museum sponsored–event brings together a panel of experts from MIT, Harvard, and Boston College exploring the scientific reasons some relationships work and others crash and burn. Learn about the neurological, physiological, and social behavior research behind gender differences, while enjoying some laughs provided by a troupe of actors from the Underground Railway Theater.

A Good Night for a Bad Date is Friday, February 13, from 5 to 8 p.m. at the MIT Museum, 265 Massachusetts Ave., Cambridge. The event is free with museum admission: $10 for adults, $5 for children under 18, students, and seniors, and free for children under 5. Take an MBTA Green Line trolley to Park Street, then an outbound Red Line train to Central Square, and walk about seven minutes. 

Love Sux at Howl at the Moon

They say single people have more fun, as this annual anti-Valentine’s bash can demonstrate. Come to Howl at the Moon for a night of dancing, cocktails, prizes, games, and live music from Howl’s famous dueling pianos. The best part: if you bring a torn-up photo of your ex, you get free entry.

Love Sux begins at 5 p.m. on Saturday, February 14, at Howl at the Moon, 184 High St., Boston. Free entry for anyone with a torn-up photo of an ex; $10 cover charge for everyone else. Take an MBTA Green Line trolley to Park Street and walk about a half-mile.

Thorns at ImprovBoston

With a motto like “Anybody who believes that ’tis better to have loved and lost has clearly never had their heart ripped out of their chest and stomped into the ground,” Thorns, ImprovBoston’s hilariously heartbreaking anti-Valentine’s show, is not playing around. The snarky comedians in this special holiday-inspired show recognize that bitterness is sometimes a funny antidote to the holiday’s usual sweetness.

Thorns is at 10 p.m. on Saturday, February 14, at ImprovBoston, 40 Prospect St., Cambridge. Purchase tickets, $18 ($14 with a valid student ID), in advance here. Take an MBTA Green Line trolley to Park Street and an outbound Red Line train to Central Square, then it’s a short walk.

If the best way to your heart is through your stomach…

Valentine’s Cheese and Beer Pairing at Aeronaut Brewery

Treat that special beer aficionado in your life with an evening of craft brews and artisan cheese pairings at Aeronaut Brewery. Guests can choose from a four- or eight-course set of pairings crafted by experts from Cambridge’s Formaggio Kitchen. A can’t-miss event for beer and Brie lovers, it’s sure to be a Gouda time.

The Valentine’s cheese and beer pairing is Saturday, February 14, from 5 to 7 p.m. at Aeronaut Brewery, 14 Tyler St., Somerville. A Half Flight Pairing (four cheeses and four beers) is $25, a Full Flight Pairing (eight cheeses and eight beers) is $45. Tickets are expected to sell out, so purchasing in advance here is recommended. Take an MBTA 47 bus from Commonwealth Avenue at University Road toward Central Square, get off at Magazine Street at Green Street, transfer to the 83 bus toward Rindge Avenue via Porter Square, and go 11 stops to Somerville Avenue at Central Street.

Taza Chocolate Perfectly Unrefined Valentine’s Day and Factory Tour

Americans buy nearly 60 million pounds of chocolate each Valentine’s Day. Those who can’t get enough should stop by Taza Chocolate Factory for a special Valentine’s Day 45-minute tour. You’ll learn how Taza produces its stone-ground Mexican-style organic dark chocolate and (of course) have a chance to sample some. Be sure to visit the factory store for some special free Valentine’s Day treats: French macaroons by Northlight Baking Company, cacao-coffee hand scrub treatments by Organic Bath Company, and hot chocolate courtesy of Taza.

Taza’s Perfectly Unrefined Valentine’s Day event is Saturday, February 14, from 2 to 5 p.m. at Taza, 561 Windsor St., Somerville. Tickets are $6 and must be purchased in advance here. Take the MBTA CT2 bus from Commonwealth Avenue at University Road five stops to Columbia Street at Cambridge Street.

Special Valentine Flavors at Sweet Cupcakes

Still haven’t had your fill of sugar? Head over to Sweet, where its famous cupcakes made last year’s Daily Meal 101 Best Cupcakes in America list. For a limited time, Sweet is serving up nine special Valentine-inspired flavors, like the Strawberry Pink Champagne cupcake, a “strawberry laced chiffon cake finished with rosé champagne infused buttercream frosting and ‘bubbly’ nonpareils” and the classic Red Velvet Cupcake.

Exclusive Valentine flavors are offered at all Sweet Cupcakes locations from Thursday, February 12, through Monday, February 16. Among its six Boston area locations is one in the Back Bay, at 49 Mass. Ave. Take any Green Line trolley to Hynes Convention Center.

For those looking for creative date ideas…

Naked at the Art Museum Scavenger Hunt, Museum of Fine Arts

Here’s a chance to mix your art history knowledge with a flash of erotica. At the Watson Adventures scavenger hunt at the Museum of Fine Arts you can explore the museum’s impressive collection of art featuring naked bodies—from nude marble statuary dating to Ancient Rome to French Impressionist Paul Gaugin’s lush depictions of Tahitian natives.

The Museum of Fine Arts, 465 Huntington Ave., Boston, offers three Watson Adventure’s scavenger hunts (Saturday’s is sold out), on Friday, February 13, at 6:30 p.m. and Sunday, February 15, at 1 p.m. Tickets are $39.50 for adults, $37.50 for college students with valid ID, and include admission to the museum; they must be purchased in advance here. Take any Green Line trolley to Kenmore Square, then the E trolley outbound to the Museum of Fine Arts.

Casablanca at the Brattle Theatre

“We’ll always have Paris.” If just reading those words pulls on your heartstrings, head over to Cambridge’s Brattle Theatre for the annual 35mm screenings of one of Hollywood’s most romantic films, the Oscar-winning Casablanca (1942), starring Humphrey Bogart and Ingrid Bergman.

Casablanca will be shown at the Brattle Theatre, 40 Brattle St., Cambridge, on Friday, February 13, and Saturday, February 14, at 4:15 p.m., 7 p.m., and 9:45 p.m. Tickets must be purchased online here; $9 for matinees, students, and Brattle members, $8 for seniors and children, and $25 for a special ticket that includes reserved section seating, unlimited popcorn and soda, and a special Valentine’s Day treat. Take a Green Line trolley to Park Street, switch to an outbound Red Line train, and get off at Harvard Square.

Swing Dancing in South Station

Feel like celebrating the holiday by dancing the night away? Suit up and don your dancing shoes as South Station is transformed into a magical ballroom for one night. The event kicks off with a free Lindy Hop lesson from instructors from New School Swing. Guests will swing to music by the eight-piece band Easy Winners. Neither previous experience nor a partner are required.

Swing Dancing in South Station is free and open to the public on Saturday, February 14, beginning at 8 p.m. with a dance lesson, followed by open dance from 9 to 11 p.m. Take any Green Line trolley to Park Street, transfer to an inbound Red Line train, and get off at South Station.

Samantha Pickette can be reached at pickette@bu.edu. Paula Sokolska can be reached at ps5642@bu.edu.