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Time for A Second Date, D.C.

Updated: Aug 12, 2019


You’ve had your first date and you hit it off – what’s next? IJL has made the first move for you – now it’s your turn. This is your chance to show them your own personal effort and see if you have a great connection. When planning a second or third date with your new interest find something to do that will really wow them! If you’re not sure what to do next – don’t worry, we are always here to help. Here are some of our recommended hot spots and hidden gems in DC to help you plan your future dates.


Create Your Own Adventure

Eleanor Roosevelt once said, “do one thing every day that scares you.” This can help with your confidence and courage. It can also help bond you and your date. So why not incorporate that into your dating experience? Whether it’s part of your norm or outside of your comfort zone create plan an experience, that natural bond is a great reason to incorporate an adventure into your date.


- One of our favorite low-risk adventures is heading down to Navy Yard with your significant other where there are plenty of restaurants, breweries and shops. The view is gorgeous, and romantic – so take turns picking out shops to experience, this way you each can get a feel for where the other’s interest lies.

- Imagine your tour vehicle suddenly changes from a car to… a boat?! DC Duck Boats allows you to feel like tourists again by both land and sea (well really the Potomac River). Together take in the beautiful sights, then top off your evening with a romantic or fun pre-planned dinner (the easy effort of having a reservation to a great place is always impressive!).


- Now if you’re really up for an all-day adventure and a bit of a history buff, why not spend your date hiking Mt. Vernon Trail. See George Washington’s estate and Theodore Roosevelt Island! As it’s all day come pre-prepared with snacks or a picnic (think healthy with a bit of something sweet, maybe even show off your cooking skills), this is way you can have some face-to-face time allowing for “getting to know you better conversation.”


*Matchmaker tip: Be prepared. If you are going on a date that requires a little more movement and activity, dress for the occasion!

Spend A Night with The Arts

For the music and arts lover in us all; Imagine yourself picking up your date and going out for a nice dinner, from there you head to spend a night fully immersing yourselves in all the arts has to offer.


- The historic Kennedy Center offers you a night of theater, concerts, opera, dance and more! What could be more fun than seeing a great show with someone then heading out to grab a drink and talk about it after!

- A definite hidden gem in the DC area is the Torpedo Factory Art Center! It is home to the nation’s largest collection of open studios – wander and admire the pieces while getting the rare chance to ask the artists questions!


- Stroll around the Sculpture Garden and admire the pieces on display while getting to know each other better! Maybe even embrace your goofy side snap some selfies with the Wish Tree!

*Matchmaker Tip: If you don’t already know, find some fun facts about what you are doing so you can show your appreciation and encourage a comfortable environment/conversation.

Food for Thought

- Enjoy a “feast of the senses” at Palette 22. Immerse yourself in their art filled venue as you and your date indulge on a variety of globally inspired meals! Who knows, you may even leave with a new piece of art to commemorate your date.


- Stroll the Wharf with your date! There are so many shops and restaurants where you can pick up an assortment of goodies to create a fun picnic by the water or even create a menu together. Maybe even pick up some specialty items from your exploration to cook your date dinner back home.

*Matchmaker Tip: it’s always fun to order multiple things and share with your date so you get the opportunity to try more on the menu. Let’s be honest, not everyone is a sharer, make sure your date feels comfortable doing so.

Not Your Average Dinner Date

Need more ideas to help you mix it up? We always have ideas—depending on the you and your date, it’s always great to have unique ideas in your “tool kit.”


- Is it a date, or a test? Either way time in an escape room is FUN. It can also be pretty insightful with your compatibility of communication, problem-solving skills while enjoying being together. DC Matchmakers recommend Escape Quest, with multiple rooms and plenty of restaurants around for after!

- Something many locals know about, but have never taken the time to actually do is check out the Mansion on O Street! The 100-room mansion has 70 secret doors—look at it a create your own adventure date…and they have different tours to choose from. See if you and your date agree with it being rated one of the top five venues to explore.


- Make sure your date is a hard-hitting success with a date that has a passion for sports—a night of baseball with the full ballpark experience is always a winning date at Nationals Park —especially when the Nationals end the night with

a big W!


- Cruise and schmooze on the Potomac Paddle Pub! Could there be any better way to get to know someone then pedaling along, having great conversation, a bit of exercise and maybe even a cocktail or two? Remember to check the forecast first and be sure to have a rainy-day contingency plan!

These date ideas just scratch the surface of all the cool things you can do in DC. Adding some effort to the planning and places you go will spice up your love life. Whether you use our ideas or come up with your own, remember to add a sense of adventure to keep the date fun! If you need help planning, call us – that’s part of our “complete dating solution” mentality.


Remember, we’ve got your back. Want to continue making a good impression on your dates? Check out our blog “Tips for a Successful First Date” for tips on leading a date and wowing your match.



Jolene Beaton is a nationally renowned matchmaker and dating expert. Her expertise, passion and unique ability to truly understand singles and the complex dating scene have made her a sought after expert in matchmaking, dating and relationships. Over the past 11 years Jolene has established herself as a leading Dating & Relationship Coach with It's Just Lunch and remains focused on one key goal – helping her clients find love.

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