Most would agree with Carrie Bradshaw that “first dates are like job interviews with cocktails.”  You’re always going in blind.  Maybe you met briefly before, but going in you have no idea what to expect.  You begin with the awkward introduction.  Then someone makes an obvious observation about the place you’ve chosen to meet.  You broach the dreaded “so tell me about yourself” line, followed up with a whole slew of anecdotal stories that touch on your high points and reaffirm how great you are.  All the while you keep the cocktails coming, as you dance around the question: is this a good fit?  And sometimes it just takes that extra “umph” to allow you to close the deal.  Fortunately for us Washingtonians, we have the advantage of drawing on a uniquely diverse city with no shortage of date ideas to give us a leg-up.

SHERRY, SHERRY BABY

Who knew all those times of watching grandma pour her Manischewitz would pay off? Sherry probably isn’t the first thing that comes to the top of your mind when you are thinking about spicing up your date game– but it should be. Shaw’s sherry and ham bar, Mockingbird Hill, is top of the list when it comes to date spots.  But don’t worry; you don’t have to be a sherry connoisseur to appreciate Mockingbird’s selection of over 50 Sherries, that’s what tasting flights are for.  Choose from a few different flights for you and your date, while Mockingbird’s experts give a brief, yet thorough, overview of each selection along with complimentary pairing snacks.  This tasting experience is sure to jump start any conversation.  And if things are going well stick around for two of Mockingbird’s signature sherry cocktails.

Where:  Shaw – 1843 7th St. NW
When:  Open daily from 5:00 pm until (depending on the day) 11:30 pm and 1:30 am.
Cost:  Flights vary in price, but are around $12.
Connect: Facebook | Twitter | Website |  Contact
photo credit:  http://dcdiningguide.com  or http://photobyjeff.tumblr.com/

CAFÉ AU LAIT, S’IL VOUS PLAÎT

Ah French, the language of love.  What better way to woo your date with a little français?  La Fourchette is one of DC’s longest standing restaurants and for good reason.  Not only is the food truly authentic, but the ambiance is as well.  And while flying to Paris for a date may be a little much, this charming bistro will make you feel as though you did.  Whether you suggest grabbing a coffee on the sidewalk patio or sharing a bottle of wine over filet mignon, you can’t go wrong.  Extra points for ordering in French.

Where:  Adams Morgan – 2429 18th St. NW
When:  Coffee starts pouring at 10:00 am on Sundays.  Dinner served daily until 10:00 pm or 11:00 pm, depending on the day.
Cost:  Coffee is a couple of bucks (refills included) and entrees average $20.
Connect: Facebook | Website |  Contact
photo credit: www.popville.com or www.washingtonpost.com

PEANUT GALLERY

We’ve all heard it before: if you want their heart, make them laugh.  Whether you’ve run out of your own material or just like stand up, Underground Comedy is one of the city’s best date night activities.  With a full lineup of daily comedy shows, you can take the pressure off yourself and instead be entertained by a number of rising stars both local and from across the country.  Given the vast variety among performers, there will be plenty of acts that speak to both your senses of humor.  It’s a guarantee against awkward silences and a comfort knowing you will both be engaged.  Not to mention the beer selection at the host locations, which happen to some of DC’s finest dives.

Where:  The Big Hunt, Bier Baron, The Wonderland Ballroom, H Street Country Club, Vendetta, Capitol Lounge
When:  As listed on the online calendar, shows start between 7:00 pm and 10:00 pm.
Cost:  Open mic nights are free!  Professional shows are $5 a ticket.
Connect: Facebook | Twitter | Website |  Contact
photo credit:  http://urbanscrawldc.com

SAAATURDAY, IN THE PARK

Chicago must have had Crispus Attucks Park in mind when they wrote their hit single, except there will likely not be a man selling ice cream.  In fact, there won’t be too many people around at all, which is why packing a picnic and heading to this secret park is ideal for an intimate afternoon date.  Tucked in between residential Bloomingdale blocks, this park has lots of green space and benches to sit, chat and snack.  If you’re up for grabbing a drink after, there are plenty of restaurants and bars around the corner.

Where: Bloomingdale – Behind the blocks of U and V Sts. NW & 2000 blocks of 1st and North Capitol Sts. NW
When: Open daily from 5:00 am – 10:00 pm.
Cost:  Whatever you spend on picnic supplies.
Connect: Facebook | Twitter | Website |  Contact
photo credit: http://crispusattucksparkdc.org or http://ragandboneslady.blogspot.com/

ROSES ARE RED, VIOLETS ARE BLUE

You’re no Shakespeare; and yes, it probably is too soon to recite that love poem you have at the ready.  To play it safe, you should leave it to the more seasoned talent and grab two tickets to Busboys & Poets’ monthly 11th Hour Poetry Slam.  This competitive late night performance poetry is the perfect way to follow up a delicious meal on 14th Street.  After enjoying two rounds of high intensity poetry and savoring a few “DC Tap Waters”, you both get to be the judge, as 11th Hour leaves it to the audience to decide on a winner.

Where: U Street – Busboys & Poets, 2021 14th St. NW
When:  Second Friday of every month from 11:00 pm – 1:00 am.
Cost:  Tickets are $5 and are available online beginning at midnight on the day of the show.
Connect: Facebook | Twitter | Website |  Contact
photo credit: fashjl11.wordpress.com or www.youtube.com or http://artistecard.com/casandrafaith