We’re so excited to finally share Will and Will’s Roosevelt Richmond restaurant engagement session! This one was a long time coming—after a few reschedules thanks to Richmond’s unpredictable winter weather (looking at you, surprise snowstorm and citywide water shutdown), we finally made it happen. And let us tell you, it was worth the wait.

A Session Filled with Personality and Richmond Charm

One of our favorite things about engagement sessions is when couples choose locations that are meaningful to them. Will and Will did just that, starting their session at Virginia Fine Arts Museum (VMFA)—a true Richmond staple—before heading to one of their favorite spots, The Roosevelt in Church Hill.

The second we walked into The Roosevelt, we could tell it was their place. The staff welcomed them with big hugs, and they felt right at home. We love when couples pick locations where they feel comfortable because it lets their personalities shine. Since we got there a little early, we had the restaurant to ourselves for a bit, which gave us the perfect opportunity to capture intimate moments—sipping wine at the bar, sharing laughs at their favorite table, and just soaking in the cozy atmosphere of one of Richmond’s best restaurants.

Why Richmond Restaurant Engagement Sessions Are a Win

Not everyone loves having their photo taken (like us for example..). If you’re someone who feels a little awkward in front of the camera, choosing a restaurant engagement session or other “activity” can be a game-changer. Instead of focusing solely on posing, you get to do something—enjoy a drink, share a meal, or just hang out together in a place you love. It makes the whole experience feel more natural and fun.

Over the years, we’ve done engagement sessions at some of Richmond’s most iconic spots, from Can Can Brasserie to breweries, ice cream shops, and picnics in the park. No matter where, we always recommend picking a location that feels like you.

Will & Will’s Epic Wedding Plans

Beyond their incredible engagement session, we are beyond excited for Will and Will’s wedding this May. These two have the coolest style—think vintage finds and knit ties—and their wedding is going to be just as unique. One Will is an opera singer (yes, really!), and the other is a vicar at a local Richmond church. Their ceremony will include a full congregation, incredible music, and a sermon that will be unforgettable.

Afterward, they’re hosting a reception for all their guests at the church before heading to River City Roll for a second celebration with their closest friends and family. Talk about an amazing way to celebrate!

Oh, and did we mention they’re working with Melissa from The Hive? That means it’s going to be flawlessly planned and absolutely stunning. We’re counting down the days!

Looking for Richmond Engagement Session Ideas?

If you’re planning an engagement session in Richmond, consider making it an experience rather than just a photoshoot. Whether it’s a cozy date night at The Roosevelt, an afternoon at VMFA, or something totally unique to you, we’re here to capture it all.

Check out some of our favorites from Will & Will’s Roosevelt Richmond restaurant engagement session below, and stay tuned for their incredible wedding this spring!

See other Richmond engagement sessions:

Maymont Engagement

Downtown Capitol Richmond Engagement

The Branch Museum