Indian Canyons

Pro Tips for Holiday Proposals

The most festive season of the year is the perfect time to pop the question… with some solid engagement advice!

Lisa Marie Hart Weddings Planner 0 Comments

Indian Canyons
The Indian Canyons is a larger-than-life location for proposals that feel romantic and secluded.
Photos by Matthew David Studio


“This is about the two of you,” says Christina Frary, photographer-co-owner of Matthew David Studio in Cathedral City. “A beautiful setting is really all that you need.”

A photographer who shoots weddings and engagements in Greater Palm Springs each month of the year might seem an unlikely source for tips on asking for your beloved’s hand in marriage. Yet Frary hears it all.

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The how-we-met stories, the first date stories, and, above all, the how-when-and-where-we-got-engaged stories. She’s privy to the best and the worst, the victorious triumphs, and the engagements that were quite nearly a debacle. (But it’s the thought that counts, right?)

Here, she divulges her best suggestions for a smooth proposal, especially if you’re incorporating it into the excitement that surrounds the holidays.


Plan the details so you're both dressed accordingly. This Idyllwild engagement was on a warm, sunny day.


Choose a Meaningful Place

“It’s a place the two of you will always remember,” Frary says. “Chose a cool, memorable location or one she’s fond of.”

Her ideas? Going up the tram to have a picnic (a whole-day event filled with anticipation), drinks and views at the Ritz-Carlton Rancho Mirage, The Parker (so many nooks and crannies to pop the question), Korakia Pensione (eclectic and other-worldly), the rugged natural wonders of Joshua Tree’s Keys View overlook or the Indian Canyons’ trails, or Ruby Montana’s Coral Sands Inn (a 1950’s throwback that is a well-kept secret).

“An at-home proposal works too, since everything is already decorated for the season,” Frary observes. “It would be pretty romantic to open up a diamond ring under the tree on Christmas Eve!”

Frary shares that her friend got engaged over tiki cocktails at Tonga Hut. It just depends on the vibe that speaks to you as a couple. “My own husband made me climb a mountain in the New York Adirondacks in the snow. When we got up there, he proposed,” recalls Frary, who has a passion for adventure and the great outdoors. “It was freezing, but certainly memorable!”


Keep holiday engagements stress-free and sincere with a simple plan.


Plan the Details

A split bottle of Champagne, dinner reservations, a staycation that night or soon thereafter — these are the little details that make all the difference. “Getting engaged is a big life event, so you should plan it like one,” Frary says. If you’re going up the tram or a road trip adventure to Idyllwild or Joshua Tree, don’t spring that on him or her. It can be cold-dress warm!


This couple found privacy in a dramatic setting at the Salton Sea.


But Keep it Simple; the Holidays can be Stressful Enough

Planning is good. But an overcomplicated engagement ordeal is one more thing to worry about amidst a busy time of year. Also consider whether you want family on hand, which could put your sweetheart on the spot and add stress. The best holiday engagements are simple, sincere, and personal. “Save the extra dressing for the wedding,” Frary quips.


Hire a photographer to capture the day.


Hire an Undercover Photographer

Visit your locale in advance to iron out the specifics of where your top-secret photographer with the long camera lens will hide. Naturally, she will come out of hiding to snap some newly engaged portraits at the word, “Yes!”

Consider a second session soon after, while the family is gathered together for the holidays.


Don’t Forget the Manicure

For the ladies in particular, suggest to her best friend or her mom that they make a manicure appointment a day or so before your proposal. “She’ll have beautiful hands for her beautiful ring and won’t feel ambushed,” Frary says.


Lisa Marie Hart has been writing about weddings since serving as an editor at Bridal Guide magazine in New York City in 1999. Since 2006, she has been editor of the annual Palm Springs Life Weddings & Honeymoon Planner. Away from the laptop, she creates tiered cupcake stands for weddings and celebrations at

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