Ladies and gents, if you are the one waiting for that ring, stop right here and forward this onto your partner.  (You can thanks us later!)


Photo Credits: Brian Tropiano Photography from Aaron and Jill’s engagement

The thought occurred to after compiling this morning’s post that while this is wedding season and couples are becoming engaged over the next few weeks, there might be some readers out there who need a friend.  They want to pop the question, but need help with the “where” and the “how.”

If you are thinking of proposing to your partner in the Washington, DC area (or any area, really) then you’ve come to the right place.  We have answers.  But, not the ones that you were looking for.  This isn’t going to be easy.  We promise though, it will be worth it.  You, too, will thank us later!

I bet you thought we’d say, book a table at Citronelle, or take a picnic to Gravelly Point, or perhaps an afternoon wine tasting at Veritas.  Guess again, my friend.  If you want to propose to your partner, you’ll have to do a little work and make it personal.  Otherwise, you’ll risk ridicule and rolled eyes for who knows how long.

You have to make the effort.  I know you don’t want to hear this because you’ve already made the mental commitment to marriage, and shelled out for the ring.  You think those should be enough, but sadly, they aren’t.  You are two thirds of the way there.  If you put some effort into planning a proposal, I can assure you, it will be worth it.  It might even be more special than the ring itself.  Not more special than your marriage itself, but this will be a great start to a wonderful life together.


  • Where you propose doesn’t really matter as along as it is important to you and your partner.  Is there somewhere special that has meaning to you two?
  • Read:  Do you like to take hikes in Great Falls or ride the carousel at Glen Echo Park?  Do you like to go for brunch in Federal Hill or Fells Point?
  • If you can’t think of a special location, think about the types of things that your partner likes.
  • Read:  Does she like to go to museums and would she get teary eyed telling friends that you took her to the National Gallery and proposed?  Would he be totally flattered if you booked a weekend at a bed and breakfast in Charlottesville?  Does she just like to lay around and relax on the weekends and would she love breakfast in bed?
  • Bottom line: The location doesn’t have to be over the top meaningful as much as it should be thoughtful.


  • If your partner was planning this out, where would he want it?  What would she like to have happen?
  • Read:  Would she really want it during halftime of the Redskins game?  Maybe she would, but maybe that’s what you would want.  Would he really want you to do it on the Metro as you are walking to work?  Maybe he would, or maybe he would be horrified.)
  • Bottom line: Step into your partner’s shoes and think about what they would want.

Advance Plan

  • Be sure to plan ahead and not just deal with things as you go along.
  • Read:  Figuring it out on the fly never works for a marriage proposal.
  • Things will go wrong.  That’s the beauty of a proposal.  It is all the funny, quirky things that lead up to the moment.
  • If you are taking her to a restaurant, call a few days before and tell them what you are up to.  Who knows, they might help you out or hook you up!?  Are you bringing flowers?  Don’t just swing by the supermarket.  Call a florist a week before, pick them up the night before and hide them in your car.  If you are taking a trip to Skyline Drive, check the directions, don’t just use your GPS.  If you are going out of town to a destination like St. Michaels, is there a festival going on that weekend that will screw things up for you?
  • Bottom line: Make a plan.


  • Once you get the “yes,” think about what you two are going to do next.  And, for the rest of the day (or weekend), really.  Its all about the post-engagement plan.
  • Now is the time to show your partner that you thought this through and planned something extra special.  You cared enough to go the extra mile.  Perhaps it is a picnic lunch for just the two of you, or walk along the C & O canal, or maybe a dinner in Old Town with your close friends and family.
  • Bottom line: Whatever it is, put some planning into the post-ring action.  Otherwise, she will be brimming with excitement and no where to go.

Bonus Points

  • Consider hiring a photographer to hide in the bushes and look onto your proposal.  You’ll get major bonus points for this!
  • Be sure to think of a creative way to have your partner dress nicely.
  • Bottom line: Life’s special moments are even better when photographed.

Best of luck with your proposal!  We are supporting you!  And remember, even if there are major disasters along they way, you will get credit for putting some thought into it and at least having a plan.

For a little extra motivation, check out this local wedding proposal that the ladies from Events in the City shared with us of their clients, Colin and Alecia.  Alecia is a teacher in Virgina and Colin crashed her school talent show, obviously getting in touch with the kids before hand to practice.  Just about the cutest 4 minutes you’ll see today!

You can also find inspiration in two beautiful engagement proposals that we’ve featured on the blog:  Aaron + Jill and Jessie + Kerry

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