How to Plan Your Engagement Session | Baltimore Wedding Photographer

Engagement

June 30, 2025
couple on beach with dog during golden hour after learning how to plan engagement session

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If you’re newly engaged, first of all: CONGRATULATIONS!! I know that over-the-moon feeling, maybe followed up with a “wait, how do we do this?” Considering you’ve gotten some details like date, venue and photographer nailed down – let’s talk about how to plan your engagement session!

Because your pre-wedding photo shoot can help set you up for success on your big day! And as a Baltimore wedding photographer, I’ve got the Who, What, Why When, and Where for you! I can help ease your mind so you step into your photo session feeling confident and excited about your “trial run” in front of the camera!

couple on beach with dog during golden hour after learning how to plan your engagement sessioncouple walks on the beach with their dog by Baltimore wedding photographer

WHO:

First things first—who should be there? Short answer: you two, maybe your dog, and that’s it. Even if you had a proposal photographer, I always recommend a dedicated engagement session with your wedding photographer. Why? Because it’s the best way for us to get to know each other and build trust before your big day. You learn my shooting & posing style, and I learn your preferred vibe for the day. Plus, we can just get to know each other more before spending one of the most exciting days of your life side by side. (Seriously, your photographer will be with you more than any other vendor!)

Thinking of bringing your pup to your session? Perfect! Just bring a handler along to help wrangle them when they’re not in the photos. Trust me, a few sweet shots with your dog are always worth it.

man and woman embrace in fall weather by Jen Harvey Photographyhusband and wife to be spin on street after learning how to plan your engagement session

WHAT AND WHY:

So, why book an engagement shoot? It’s more than just crossing “photos” off the wedding to-do list. This is your chance to get comfortable in front of the camera, practice posing, and see how I work. Almost every couple tells me they feel awkward before we start… and then they end up laughing, relaxing, and genuinely enjoying themselves.

One of my couples, Cyleena and her partner (pictured above!) were also nervous. But look what they were saying by the end!

“Jen is the best, and we are beyond thrilled and grateful we found her. From the moment we met her for our engagement photos, I knew I was in amazing hands for our wedding day. Jen is so caring, truly feels like a friend, and her work is beautiful. Our photos are timeless, romantic, and we will cherish them forever in our home.” — Cyleena R.

That’s the feeling you’re going to walk away with!

man and woman share cheers on picnic blanket by Jen Harvey Photography

WHERE…

The next step in how to plan your engagement session:

Location, location, location! The best engagement session spots are meaningful to you—where you got engaged, your family’s beach house, your favorite hiking trail, or even the ice cream shop you visit every Friday night. Baltimore and the DMV area are full of stunning backdrops, and I’m always happy to share my favorite hidden gems if you’re stumped.

Want to venture outside Maryland? Let’s do it! I love traveling for couples and finding those perfect, unique spots that feel like you.

man and woman walk on the beach after learning how to plan your engagement sessionengaged couple kneels with dog on beach by Baltimore wedding photographer

WHEN:

When should you book your photo shoot? My advice: as soon as you’re ready! Planning ahead gives us more flexibility for weather hiccups and ensures you get photos in time for save-the-dates. Plus, it’s a nice way to express and celebrate all the happy feelings of being engaged!

Think about your favorite season: some couples love spring blooms, while others choose the opposite vibe of their wedding season for variety.

Sessions typically happen Monday–Thursday, about 1–2 hours before sunset. That dreamy golden hour light? It really is worth it.

couple hold hands in front of old house after learning how to plan your engagement session

woman in blue dress embraces man in white shirt by Jen Harvey Photography

Okay now that we’ve talked about how to plan your engagement session, let’s talk about some extra pro tips for a seamless experience.

A few extra bonus quick tips to make your photo shoot feel effortless:

  • Schedule your makeup trial for the same day. You’ll look flawless and get to see how your wedding-day glam photographs. Win-win!

  • Treat yourself to a manicure: your hands (and that ring!) will get plenty of camera time.

  • Don’t stress about outfits, I’m always happy to help you plan looks that feel like you. We can email and text outfit plans!

  • Bringing your pup? Consider hiring a pet handler like Furever & Always so you can focus on each other when your dog’s off-duty.

engaged couple walks up steps by national mall by Jen harvey photography formal couple walks at national mall by Baltimore wedding photographer

LET’S PLAN IT TOGETHER

If you’re dreaming up timeless, romantic engagement photos that feel like you, I’d love to help you plan every detail. Reach out today and let’s make it happen—your engagement session should be just as special as your wedding day.

Contact me here!

man and woman kiss in the street after learning how to plan your engagement session couple embraces tightly next to the water by jen Harvey Photography man spins woman around by Baltimore wedding photographer

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Hi, I'm Jen!

I'm a photographer, a guide, and a quiet calm in the middle of your most meaningful day.

I’ve always been drawn to emotion — to the joy in a father’s eyes during the first look, the soft nervous energy right before the ceremony, the tiny, fleeting in-between moments most people miss. Capturing those is what I do best.

My work is grounded in empathy, trust, and intention. I’ll support you through the planning, walk you through the timeline, and ensure that you feel seen and celebrated from start to finish.

This isn’t just about pretty pictures — it’s about preserving what matters, so you can return to it again and again.

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