Proposal and Engagement

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CT Proposal & Engagement Photographer Serving New England

Romantic, candid proposal and engagement sessions on 35mm film and digital

Your engagement is more than a milestone — it is the beginning of a new chapter. At Where We Wandered Photography, we document proposals and engagement sessions with a nostalgic blend of 35mm film and digital photography, creating images that feel honest, cinematic, and deeply personal.

Whether you are planning a surprise proposal in Connecticut or celebrating this season of your relationship somewhere in New England, we create photographs that preserve the feeling of it all — the nerves, the joy, the laughter, and the quiet in-between moments you will want to remember forever.

Surprise Proposal Session

Planning to ask the biggest question of your life? We help you create a proposal that feels seamless, personal, and unforgettable. From location ideas and timing to discreet coverage of the moment itself, we make sure you can stay fully present while we document every reaction as it naturally unfolds.

Engagement Session

Engagement sessions are a chance to slow down and document your relationship as it is right now. Rather than forcing awkward poses, we guide you in a way that feels natural so your images reflect genuine connection, movement, and emotion.

The result is a collection of photographs that feels relaxed, romantic, and unmistakably like you.

Based in Connecticut, Serving New England

Where We Wandered Photography is based in Connecticut and photographs proposals and engagement sessions throughout New England, including Massachusetts, Rhode Island, Vermont, New Hampshire, Maine, and New York. We are also available for destination sessions and proposal photography anywhere in the United States.

Plan My Proposal or Engagement Session

Proposal Photography

Surprise Proposal Package - $500.00

Perfect for couples who want the proposal documented with intention, emotion, and a few just-engaged portraits right after the moment.

At Where We Wandered, we help you plan a proposal that feels personal and unforgettable, then quietly document every reaction — from nervous anticipation to the instant your partner says “yes.”

What’s Included

Complimentary planning call with a dedicated proposal photographer to talk through your vision, nerves, and ideas.

Help with location scouting so the setting feels meaningful and photographs beautifully.

Custom timeline creation to keep everything running smoothly, from arrival to the big question.

Discreet coverage of the proposal itself, focused on genuine reactions and emotion rather than staged poses.

A relaxed engagement-style portrait session right after the proposal so you walk away with both the moment and beautifully composed images together.

Exclusive savings when you book Where We Wandered for your wedding photography, so your story is documented consistently from proposal through “I do.”

Sunset beach proposal featuring a silhouetted couple by the ocean, kneeling to propose.

Engagement Photography

Engagement Session - $400.00

You said yes — now let’s document this season before it becomes a blur. Engagement sessions are a chance to slow down, celebrate where you are right now, and create images that reflect your relationship in a way that feels relaxed, romantic, and true to you.

We guide you with a mix of candid prompts and natural posing so your photos never feel stiff or overdone. The result is a gallery full of movement, connection, and genuine emotion.

What’s Included

1-hour engagement photography session with guidance on posing, prompts, and movement so you never feel awkward in front of the camera.

Location scouting and planning support to find a setting that fits your story — from downtown streets to quiet New England trails or coastal views.

A mix of candid moments and lightly posed portraits that capture the essence of your connection and personality as a couple.

30 professionally edited, high-resolution images delivered in an online gallery, ready to print, share, or use for save-the-dates.

Exclusive savings when you book Where We Wandered for your wedding photography, so your proposal, engagement, and wedding day are documented with a consistent, cohesive style.

Romantic couples portrait at at golden hour, featuring a man and woman embracing iby the ocean

Reach out and we’ll start planning within 24–48 hours

Editorial Proposal and Engagement Photography