Over the years, Sarah and I have had the joy of photographing more than 25 surprise proposals as we watched young men ask a single question that would change the course of their lives. Between that and my own experience of proposing to Sarah, we’ve learned a lot! I certainly wish I had all this information before I got down on one knee!

 

But now it’s our turn to pass along our experience and wisdom to every guy out there wondering to himself, “How do I propose to my girlfriend?” Every week throughout this Spring, we’ve been posting an updated version of this 2018 blog series. It’s mostly written as a note directly from me, Hunter, to all the guys out there who are exactly where I was back in 2016: head over heels in love with a girl, with absolutely no plan on how to ask her to be yours! Sarah even chimed in with some of her input to the ladies who think the big question might be coming soon!

 

A Guy’s Guide to Proposing Well Part 5: Where to Propose

 

Welcome back guys! Last week, Sarah took over the series and spoke to all the ladies out there wondering if and when their boyfriend is going to pop the big question. This week, I’ll be helping the guys think through great locations to ask the big question! Like we mentioned in Part 3, sometimes you get lucky and the decision of where to propose is already made for you.

 

Maybe an upcoming family vacation or other big life event has presented itself as the obvious time and place to propose, so there’s no need to decide on a location. But for many of the gentlemen out there, you’ve simply chosen a nice fall, spring or holiday weekend as the ideal time to propose, and you have an entire city as your oyster. How do you begin to narrow down the hundreds or even thousands of locations that could make the proposal even more unforgettable?

 

 

First: Think Sentimental

For starters, we always ask our guys to consider sentimental value. For those who grew up or went to college in Charlottesville, there are spots that will immediately come to mind like UVA’s Lawn or Charlottesville’s Downtown Mall. In the late-Spring of 2019, our guy Matt and his girlfriend Christy dropped off their final assignment during their shared time at UVA Law School. As they walked out of the building and onto the Law School’s lawn, he got down on one knee right there and made their celebration complete!

 

Think about milestone moments in your relationship, and ask if there are any locations associated with those moments. Maybe you asked her out for the first time in a local park, or your first date was to a really beautiful winery. Maybe those special three words “I love you” were exchanged for the first time on a location that would be perfect to revisit as you ask her to marry you! Perhaps it’s as simple as a location that you both love and have visited a lot throughout your relationship.

 

However, we know that not every couple has those “go-to” locations that you think of as special to your relationship. Or maybe you’re planning on popping the question while you’re out of town for the weekend visiting a new city or a go-to vacation spot. If that’s the case, read on!

 

 

Second: Think Beautiful

Most of the surprise proposals that we photograph and help plan are for couples visiting Charlottesville from out of town. They don’t have any particularly sentimental locations in town, so the guys ask us for something that simply looks great!

 

If you’re lucky enough to live or get engaged in a city like Charlottesville, then you certainly won’t be short on beautiful locations to propose. Although Charlottesville is one of the largest cities in Virginia outside Hampton Roads and the DC-area, it’s surrounded on all sides by majority-rural counties. At our last count, there are over 60 wineries and vineyards in Albemarle County (which surrounds C’ville on all sides) and the eight counties that surround it. That means that for someone staying in Charlottesville, there are dozens of options within a brief car ride, and that’s just considering locations that make wine! We didn’t even count the cideries, breweries, distilleries, meaderies and farms that also cater to visitors and serve delicious food and beverages.

 

Why do these locations make for such great proposals? Many of them boast incredible views of the surrounding landscapes, and almost all allow professional photography for free or for a very reasonable fee. However, make sure you contact them well in advance to coordinate your plan with them! Most will ask you to respect their business hours and have professional photographers check in with them before going to their hiding spot.

 

 

More Aesthetic Options

If you still want the natural aesthetic but without the restrictions of a private venue, explore some of the local parks in your area. I asked Sarah to marry me in one of Charlottesville’s many scenic parks!

 

If you and your lady are into a more urban feel, look to your city’s downtown area. Charlottesville’s downtown mall not only features a lot of the architecture that’s characteristic to Charlottesville (think red brick meets more red brick, oh and columns too!), but also lights up each December with beautiful Christmas decorations!

 

However, we know that for some odd reason, not every couple in the world will get engaged in Charlottesville, Virginia! So do some research, and look into similar places in your own town or vacation spot. If you will be getting engaged in the Charlottesville area, reach out to us, and we’re happy to give suggestions on some of our favorite spots in town!

 

 

Third: Think Rain Plan

Something else to keep in mind is the one thing that is 100% out of your control: the weather! The most beautiful outdoor location in the world won’t do you much good if it’s pouring down rain and you can’t step out of your car. So as you think about where you’ll be proposing, keep this in the back of your head. Plus, since she’ll think you’re heading to this location to try some wine/get a bite to eat/go for a walk/hang out for a bit, if that activity doesn’t make any sense in the rain, then your cover might be blown.

 

Some vineyards in the area have covered areas like balconies or patios that can be reserved for an event like a proposal. We’ve even had to reschedule a proposal once or twice due to rain, capturing it the following day! As with all things, stay flexible when rain is in the picture and be open to last-minute changes. In the end, location can really enhance a proposal, but what it really comes down to is the agreement of two people to spend the rest of their lives together, and the beginning of that process!

 

 

Sarah and I hope that this blog series has been a huge asset to couples out there as they walk the road to engagement! We’ve already had friends and clients alike say that they’ve found it helpful (or have been sending it to their boyfriends with lots of winking emojis). Stay tuned for next time as we finally address the most important section of all: a step-by-step guide to getting down on one knee and asking the big question!

 

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Check out the rest of the series at the links below!

• A Guy’s Guide to Proposing Well Part 1: Four Questions to Ask Yourself Before You Get Engaged
• A Guy’s Guide to Proposing Well Part 2: How to Pick the Right (Sized) Engagement Ring
• A Guy’s Guide to Proposing Well Part 3: Planning the Big Day
• A Guy’s Guide to Proposing Well Part 4: When is My Boyfriend Going to Propose Already??
• A Guy’s Guide to Proposing Well Part 6: How to Propose to Your Girlfriend
• A Guy’s Guide to Proposing Well Part 7: How to Make a Weekend Out of It

 

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If you’re interested in planning your own surprise proposal, click here to get in contact with us!