Date Ideas, Fun

Date Night – Pinstripes and Filomena

Waiting for our lane to open!

My boyfriend and I have been dating a little over a year and it surprises both of us, the amount of new and exciting dates we are still able to go on, in D.C.!

A few weeks ago, we headed to Pinstripes in Georgetown to compete (against each other – we’re competitive) in bowling, and then across the street to Filomena for dinner.

Below is everything you need to know for both – we hope you enjoy this date as much as we did!


By the time I finished applying my filter, he had already beaten me.

Pinstripes has a full restaurant and bar, as well as bocce courts and bowling lanes (which also has a menu and servers).  It’s an intimate space with comfortable couches – something you’d expect from a boutique bowling alley in Georgetown.

We played for two hours (which is about four games for two people).  Naturally, I only won 1 out of the 4 (even though I did most of the trash talking).  From the appetizers, to drinks, to bowling – we had an amazing time and can’t wait to come back with our friends!

Things to Note

  • It books up super fast (there aren’t many lanes), so I was lucky to have booked it a few weeks in advance.
  • We went on a Sunday – I’d advise against that and go any other day/evening.  It’s mainly families on Sundays, and we waited an extra 30 minutes, past our reservation, to get escorted to our lane.
  • Bowling was $20 an hour and shoes rental was $5 a person = $50
  • We ran into friends on the way in and they suggested heading to Pinstripes for brunch ONLY, on Sundays – apparently the chocolate fountain is to-die-for.


The tiniest snapshot of how it was decorated for Christmas – I didn’t want to be that person taking pics of everything – at least this time.

Filomena is one of the oldest restaurants in Georgetown, still-in-existence, and it’s also one of my favorite authentic Italian places to eat, of all time.  If you have ever been to Italy, you will appreciate the old-world Italian feel, the waiters in tuxes, the extensive food and wine menus, and the digestif that comes post-meal (not to mention the Nona in the window, making fresh ravioli).

Sambuca with 3 coffee beans (for health, wealth, and happiness) and an Amaretto, courtesy of Filomena (there might also be leftover wine in there too).

It had been some time, since I had been in there. I had also never been in there, during the holidays.  Thus, it felt like an entirely new experience, walking down the stairs and being greeted with the most amazing display of Christmas I have ever seen.  If you have never been, GO BEFORE THE HOLIDAYS ARE OVER. I don’t want to ruin the surprise but I’m still in awe over how many hours it had to have taken to decorate every square inch of that place!

Things to Note:

  • Since Filomena made a comeback in recent months, the reservations can be hard to find – book early!
  • There is gluten-free pasta available, for those of us who need/prefer it
  • Read the menu – it’s entertaining!  It tells tales of who has visited the restaurant and why they came back again and again
  • Drink the wine – they have some of the best Italian wines at all price points
  • Accept the digestif – they even leave the decanters on your table until you are finished
  • It’s very romantic – there were couples everywhere
  • You are treated like a VIP – it’s rare to find a restaurant that has such impeccable service

Have fun!



1 thought on “Date Night – Pinstripes and Filomena”

  1. One of my first dates with my Italian boyfriend was drinking ‘ Flaming Sambuca Shots with 3 beans’. He wanted to get me ‘ happier’, but it ended him been the ‘happiest’.

    I agree, Italian restaurant’s with the ‘old world charm’ have the greatest food & ambiance.


Give me your thoughts!

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s