20 of the best surprise holiday proposal photos ever (and what to expect for your own proposal!)

surprise holiday engagement proposal at a christmas tree farm

Michael James Photography via How He Asked

It’s that time of the year. Cozy sweaters, fireside cuddling, hot chocolate, family time, and snow days… it’s no wonder that this romantic season is one of the most popular times of the year for a proposal! If you’re hoping for a diamond on your finger rather than presents under the Christmas tree this year (or maybe you can have both, why not?) then there’s a few things you need to know.

  • Getting proposed to is awesome
  • You’ll probably cry, even if you have fair warning
  • You won’t be able to stop looking at your finger at least 3 months
  • Choose when to tell friends and family wisely — because once you do, wedding planning officially starts!

I’ll be honest — there’s not much you can do to prepare for your holiday proposal besides keep your nails manicured… just in case. So instead, why not dream of the big moment by checking out these oh-so-romantic winter proposals below?

surprise winter proposal in Central Park. Her reaction is perfect!

Raquel Bianca via How He Asked

surprise engagement in a park! She looks amazing, and so surprised!

Spanglish Studios Photography via Inspired By This

gorgeous fall surprise proposal in a park. yes, please!

Bobbi + Mike via How He Asked

the perfect reaction to a surprise proposal in Paris

Munaluchi Bridal

everything about this surprise fall proposal is absolutely perfect

Melissa Green Photography

surprise proposal. capturing a photo like this would be priceless!

Sterling Graves via How He Asked

amazing surprise proposal in san francisco.

Josh Gruetzmacher via Green Wedding Shoes

the best surprise winter proposal in the snow that I've EVER seen!

Chris Emeott Photography via How He Asked

adorable snowy surprise proposal photo

Ciara Richardson via Bridal Musings

this adorable surprise proposal photo is PERFECT!

Jessica Janae Photography via Makenna Alyse

a surprise proposal during the couple's trip to Scotland. the photos are adorable!

Kitchener Photography via Green Wedding Shoes

surprise winter proposal in the snow. This photo is priceless!

David Wittig

A surprise proposal in the park. Her reaction is priceless, I need photos like these!

Katie Jane Photo

A romantic surprise proposal photo!

Stephanie Parsley Photography via How He Asked

A surprise winter proposal. This photo is amazing!

Cassandra Eldridge Photography via How He Asked

A surprise proposal in the rain. Who knew the rain could be so romantic?

Mark Williams Studio via Green Wedding Shoes

A surprise winter proposal photo. Love this!

Gray Photography via How He Asked

A surprise holiday proposal while ice skating.

Jeff Loves Jessica via Wedding Chicks

A surprise winter proposal -- love this photo!

John Hays Photography

If you’ve just had your own proposal, congratulations! A holiday engagement is an amazing time to spend celebrating with friends and family, so you should do just that! Pin your favorite proposal above… just in case your special someone needs a little hint!

PS — If you want even more magical proposal photos and heartwarming engagement stories, make sure to check out How He Asked. Proposals galore!