A well-planned proposal How one man surprised his sweetheart

By Molly Milroy

Alex Comstock wanted to give a surprise proposal to Andrea Ruberg. Since they had already been together for seven years and had talked about getting engaged, he knew surprising her would be difficult, if not impossible.

So how did he pull it off?

It took a lot of coordination and preplanning. Comstock, a local photographer and videographer who has worked with The Woman Today, first reached out to Ali Carlson, an account executive at the magazine.

“I had Ali email me a fake assignment. If worse comes to worse, I had an email to show Andrea,” he explained.

Then Comstock coordinated with Ruberg’s family, even having her sister, Sam, fly in from Montana, all without Ruberg’s knowledge.

“She thought it was happening in April, since her sister already had a trip planned to be home at that time,” Comstock said.

After scouting out the perfect location, one that included a hiding place for friends to capture photos and video, he settled on Brighton Beach in Duluth. A stone structure near the water served as the hiding spot.

It was all planned for that Saturday. Earlier in the week he approached Ruberg requesting her assistance in shooting a cover for the magazine. At first, she was hesitant, not wanting to be in the photo. But not pressing too hard on the issue, he told her he could find someone else.

Fortunately she finally complied.

When the special Saturday arrived, Comstock told Ruberg they needed to do the photos in the morning (prior to the 1 p.m. lunch he asked her mom to coordinate).

“The last hour, she started to get a little fishy and said, ‘What if I don’t want to do these photos?’” Comstock said. “And I replied, ‘Well, that would stink, because the deadline is tomorrow. Do you want to see the email?’”

After scrolling through a week’s worth of emails, he located the one from Carlson and showed her, which settled it for Ruberg.

Ruberg’s sister and friends arrived at Brighton Beach ahead of time and cleared out the area of people milling about. Then they hid in the stone structure. When Comstock and Ruberg arrived, he had her stand on a rock near the water for the photo assignment. With her back turned, he started snapping photos. The signal for the group to come out from hiding was when he released a drone up to the sky.

“‘All right you’re good to go with the pictures,’ I told her, and when she turned around, I was on one knee,” Comstock said.

As for her answer?

“She barely could get anything out,” he said with a grin, “but it was a ‘yes.’”

When Ruberg saw her sister and friends standing there, it took the surprise proposal to a whole new level.

“Alex knew I wanted my sister there and was so happy she was,” Ruberg exclaimed. Afterward, they all headed to Ace’s on 29th in Superior where 15 more family members and friends were waiting to celebrate with them.

“The best thing about the proposal was how planned out Alex was,” Ruberg expressed. “I give him a lot of credit as I’m a hard person to surprise.”

Their wedding date is set for July 16, 2022 at The Grainary in Poplar, Wisconsin. D