Real Proposal Story: An Outdoor Engagement Overlooking San Francisco Bay

California, Proposals

First comes love, then comes marriage. But before the joy of wedding planning begins, comes the biggest, happiest question of all: Will you marry me? Thanks to HowHeAsked, we found some real, romantic, and ridiculously creative proposal stories that will get you inspired, tearing up, or both!

Jen and Kohl met when she was an emergency fill-in for a friend's intramural sports team. As soon as Jen spotted her future husband warming up, she told her friend—who is now her maid of honor—"Oh my gosh, who is that? He's so cute!!" Her friend's response? "He's one of our good friends, I knew you'd think he's cute."

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Jen's friend was right. After a few weeks of meeting up on the field, discovering mutual friends, and even taking classes in the same classrooms, the fellow students finally exchanged numbers and the rest was, as they say, history.

Five years later, the Southern California-based couple planned a trip to Jen's hometown of San Francisco to celebrate their anniversary and Kohl's birthday. The duo had discussed marriage, and even how they'd get engaged: Jen told her future husband that she wanted the moment to be intimate and have someone capture the entire thing.

Luckily, her family had some thoughts of their own. Jen's mom booked a room at the Omni Hotel in San Francisco, which raised her suspicions. She was so curious about the possibility of a proposal that she called her brother, who told her to check Kohl's backpack for an engagement ring. When she came up with no dice, she went ahead with the trip like business as usual.

On proposal day, the pair planned visit the Marine Mammal Center and Point Bonita Lighthouse in Sausalito. Though the plans were exciting, the weather was not so fun for Jen. "Our visit at the Mammal Center ended a little early so we headed to the lighthouse for our private tour," she says. "It was an extremely cold day in the city, but being so used to SoCal weather had made us unprepared for the cold. Freezing, I rushed Kohl and asked to see if we could do it early. He agreed and we started walking to the lighthouse. He stalled a couple times to take pictures and even asked to sit on a bench and wait."

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At the end of their lighthouse tour, Jen was ready to go inside, but Kohl instead asked her to pose for some pictures.

"Before we left he asked to take a picture of me at the end of the bridge—it was his way of placing me in the right position," Jen recalls. "He took the picture then said, 'I have to ask you a question...' but in the corner of my eye I saw a man army crawling on the ground and became so confused."

Kohl tried asking his question again, and this time, Jen looked at him. He got on one knee and said, "Jen, I want to ask if you'd spend forever with me?" As Jen cried, said yes, and let her new fiancé put the ring on her finger, she realized that the man crawling on the ground was actually the photographer he hired to capture the entire proposal—exactly how she wanted.

The newly betrothed couple ended the night with Jen's parents for dinner at the Farallon and celebrated the following day at the California Science Center.

Our Takeaways

1. Say what you want: Women should have a say in the first part of the rest of their lives! Jen's only request was to get the moment captured on camera, a great idea no matter whose it was. Clearly, she felt Kohl listened to her. "It was such a well-planned and thoughtful proposal," she says. "It was also a complete surprise! He did such a great job with all the details and even custom designed my ring—it was just perfect!"

2. Let your family fool you: Adorably, Jen's mother and brother threw her off the scent more than once. Thanks to their stealth, she got the surprise of her life.

3. Pick a pretty backdrop: The Point Bonita lighthouse is set on a stunning spit of land outside San Francisco. Kohl had the bright idea to use a photo op as an excuse to get Jen in front of the prettiest view possible. Thanks to his smart planning, they got that drop-dead gorgeous reaction shot.

4. Go with the flow: Even though she was cold, Jen sat outside on a bench and walked around outside with her future husband. It's a good thing she sucked it up—if she'd really complained, the proposal might have had to proceed differently!

Click here to read more about Jen and Kohl's engagement.

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