New Haven, Connecticut Engagement Session

Madeline & Anna’s Playful, Personal Engagement Session in New Haven, Connecticut

If you’re thinking engagement photos have to be all sunset gazes and formal outfits, allow Madeline and Anna to gently (and hilariously) prove you wrong. Their New Haven engagement session was cozy, playful, wildly meaningful, and absolutely them: featuring cats, board games, arcade battles, and all the love in the world.

From Cats to Competition: The Story Behind the Session

Madeline and Anna didn’t just choose cute locations, they chose places that built the foundation of their relationship. We started the afternoon at their apartment, where they snuggled on the couch with their two cats, Cosmo (the bold orange boy) and Benny (short for Benoit Mandelbrot, the friendliest tabby ever). With tea in hand and sunlight pouring through the windows, the whole space felt like a warm, quiet moment.

From there, we headed to Barcade, where Anna proposed after dominating a game of Shuuz- an obscure but now legendary horseshoe arcade game. This place was empty except for us, and they had the entire space to themselves to laugh, battle, and sneak kisses between rounds. The glowing lights, the silliness, the history… it was all so them.

Last stop: Elm City Games, the board game shop where they first met during a party games night. We recreated their first connection, complete with favorite games, stacks of strategy cards, and lots of quiet, meaningful glances across the table. It was the perfect bookend to their story so far, and a beautiful bridge to their wedding next year.

Why This Session Was So Special

Madeline and Anna are the kind of couple that just clicks. Their chemistry? Effortless. Their vibe? A perfect mix of spooky, intellectual, and endearingly quirky in the best way. Photographing them felt like hanging out with old friends. They barely needed posing because they just fit. Every location, every detail, every laugh was filled with meaning.

If you’re considering doing an engagement session that reflects who you are (not just what looks cute on Pinterest), let this be your sign. Photos are way more powerful when they’re personal. Let’s find the spots that mean something to you and make some photo magic.

FAQ: Engagement Sessions in New Haven, CT

1. Where are the best engagement session spots in New Haven?
Some of my favorites are downtown neighborhoods for cozy home vibes, Barcade for arcade energy, and Elm City Games for game lovers. East Rock, Yale’s campus, and Wooster Square are also perfect.

2. Should we include pets in our session?
Absolutely. If your pets are part of your love story, bring them in! Cosmo and Benny were total stars and made for the coziest start to Madeline and Anna’s session.

3. How long should we plan for an engagement session?
Most sessions run around 90 minutes to 2 hours, depending on how many locations we visit. We took our time walking between spots since everything

was local, and it made the experience super chill.

4. Can we make our session unique to us?
YES. Please. Let’s skip the Pinterest checklist and build something that actually feels like your relationship. Whether that means arcades, cats, or cozy board games, I’m here for it!

5. What should we wear?
Whatever makes you feel like yourselves! Madeline and Anna kept it comfortable and true to their everyday style, which made the whole thing feel genuine, easy, and fun.

Madeline and Anna’s engagement session was the perfect reminder that love stories aren’t one-size-fits-all. They’re cozy, they’re weird, they’re joyful. They’re full of cats and inside jokes and neon-lit arcade games. And I’m so excited to document their next chapter at Roseland Cottage in 2026!!

LGBTQ+ couple laughing in their New Haven apartment kitchen while holding their tabby cat during cozy engagement photos
Madeline and Anna sharing a quiet morning moment while sipping coffee and cuddling with their cat in their kitchen
Couple holding hands and dancing in their New Haven apartment kitchen during a playful engagement session
Anna and Madeline wrapped in a hug near their kitchen wall, cozy and joyful during their in-home photo shoot
Both partners sitting on a green couch as their cat lounges on one of them in their sunny New Haven apartment.
Board games stacked on a shelf with the couple cuddling on the couch, captured during their Elm City Games-inspired engagement shoot.
Madeline laying on the floor with their orange cat while Anna laughs nearby in their New Haven apartment
Portrait of Benny the tabby cat looking toward the camera while his humans laugh in the background
Couple laughing together in their living room surrounded by books, board games, and cats
Madeline and Anna slow dancing in their apartment surrounded by books and cozy vibes
The couple lying on the couch, full of laughter and love, sunlight pouring in
Soft, romantic moment as the couple embraces in a sun-drenched living room corner of their New Haven apartment
Couple hanging out in their sunlit apartment living room surrounded by plants and cozy home decor
A photo of the couple walking side-by-side downtown after visiting Barcade in New Haven, Connecticut.
Dramatic photo of Anna and Madeline in stairwell shadows on the way back to their New Haven apartment
Couple striking playful poses under arcade lights during their Barcade engagement session in New Haven, Connecticut.
LGBTQ+ couple holding each other and smiling in front of vintage arcade cabinets at Barcade New Haven
Anna sitting at an arcade game while Madeline playfully leans in, surrounded by nostalgic games
Smiling together while walking past retro arcade games at Barcade in New Haven
Intimate moment as the couple cuddles near the arcade cabinets at Barcade during their New Haven engagement session
Anna making a playful face while competing at Shuuz, the arcade game where she proposed
One partner cheers while the other plays a retro arcade game, both grinning at Barcade in New Haven
Smiling mid-dance between arcade machines during their engagement session
Goofy, joyful photo of Madeline leaning into Anna at Barcade during their New Haven engagement session
Playful photo of Anna and Madeline dancing together in the aisle of the Barcade arcade
Madeline and Anna enjoying a quiet laugh while surrounded by vintage arcade games
Sharing a kiss while leaning over a vintage pinball machine at Barcade in New Haven
Embracing over a pinball machine, sharing a quiet, glowy moment at Barcade in New Haven
Sitting close at an arcade table game, cuddling and smiling during their engagement session
Laughing with heads thrown back, arms around each other, surrounded by classic arcade games
LGBTQ+ couple sharing a quiet moment while sitting at the arcade bar at Barcade in New Haven, Connecticut during their engagement session
Couple seated at a café table arm-wrestling and laughing, showing off their playful chemistry during their New Haven engagement session
Joyful couple laughing together inside Barcade, with arcade games glowing behind them during their engagement photo session
Intimate photo of Madeline and Anna facing each other at a high table by the window, framed by reflections of arcade lights
Close-up of the couple holding hands on a comic book-themed café table, showcasing their rings and connection
Laughing nose-to-nose by the window, soft reflections of arcade lights around them.
Sitting across from each other at a comic-themed table, deep in conversation with soft light streaming in.
Cozying up by the window, one leaning their head on the other’s shoulder with peaceful smiles
Standing between shelves of board games, playfully chatting and laughing
LGBTQ+ couple sharing a playful moment over a board game at Elm City Games in New Haven, Connecticut during their engagement session
Close-up of hands as Anna gently places a ring on Madeline’s finger, surrounded by board games and natural window ligh
Engagement photo of the couple sitting across from each other at a round table with board games like Cascadia and Dixit
Anna smiling while watching Madeline play a board game during their Elm City Games engagement session
Wrapped in each other’s arms between rows of board games, backlit by string lights.
Madeline and Anna embracing in the board game aisles of Elm City Games, surrounded by colorful shelves and cozy lighting

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