How to Secretly Propose to Your Girlfriend

Chantel + Monique

Earlier in their relationship, Chantel had popped the question to Monique. Since they’re a perfect match, she said yes. They’d been living in Southern California and knew they wanted to live in San Francisco. When Chantel scored a job at a real estate management company that included a free apartment in this pricey city, they packed their bags along with their giant dog, Big Sur. They headed up the coast, probably holding hands with Big Sur squeezed between them! Since they were already engaged, it seemed apparent that the next step would be to plan their wedding. But not so fast, because Monique also wanted to propose to Chantel!

Monique emailed me explaining that she really, really wanted to get down on one knee to propose. She loves Chantel so much, and she wanted to see the look on her love’s face when she asked her to be hers forever and slid a beautiful ring onto her finger. They live in a small apartment, and it’s impossible to have any secrets when they’re both home. We had to be so careful with communicating that Chantel wouldn’t be tipped off. All the secret planning paid off, though, and the secret proposal plan was executed flawlessly.

How do you plan a surprise proposal?

1. When Planning your proposal speech, speak from the heart. Talk about why you love them and want to marry them.

2. Ask friends to help. This can include distracting the person getting proposed to or perhaps asking them to get a manicure for a “girls’ day” so they don’t suspect they are about to have their hand photographed.

3. Make sure the ring is sized correctly and already insured.

4. Hire a professional photographer or videographer. You’ll want to share the happy news immediately.

5. Select your location and arrange to have the proposal delivered there. Most photographers can help with this planning.

She booked her photography session, and I suggested a picnic in the park. Luckily, next door to their apartment is a secret garden. It’s technically on land not used by a local firehouse, and the neighborhood senior ladies had commandeered it for their gardening. Nobody is going to argue with them. It was dark, romantic, lush, and perfect for this surprise proposal. We had recently teamed up with Alex of The Picnic Plug. We were excited about this was our first chance to try them out. Alex showed up with a boatload of pillows, tables, charcuterie, bubbly, very classy boho tableware, and fresh flowers! I literally couldn’t believe the giant cart she rolled up with.

Chantel works long hours, and the day of the surprise proposal had to go perfectly. Monique contacted Chantel’s boss to tell them about her plan and hoped they would cooperate. Fortunately, they were romantics, and she was kicked out of the office at 5pm. While she thought it was strange, she was excited to go home early and see Monique.

When she walked in the door, nobody was home! She peeked into their bedroom and was blown away by what Monique had set out for her. She’d bought her a beautiful new dress (it fit perfectly) and left out her accessories, makeup, and even a note in the bathroom that her curling iron was already heated up. Monique had also set up an incredible art display of Polaroid photos hanging from the ceiling, documenting their love story, and a special big sign asking her to meet in their secret garden. But the biggest surprise was yet to come.

The three of us and their pup were all up in the garden, anxiously awaiting her arrival and pacing around like crazy people. Finally, we heard her coming, and we all took our places. Monique dropped to one knee just behind our white light-up marquee letters that said “Marry Me.” You should have seen the look on Chantel’s face as she took it all in. Life has a lot of moments, but this one was beautiful, perfect, and so emotional. The pictures will tell the rest of the story, and their wedding is in just a few days. I’ll post part two of their story on the blog in a few weeks, so don’t forget to return for part two!