When Jenna Met Drew

The  Kutchers prove that it is, indeed, possible to "make two lovers of friends"

They were kind of lukewarm about each other when they first met. But the more their paths crossed, the more they came to appreciate each other, and the two became fast friends. Over time, that friendship blossomed into something more. At first their nascent romance lead to nervous retreat, as well as a few emotional outbursts and mild recriminations. But in the end, the two lovers stopped fighting fate, admitted their strong feelings for each other and were eventually married.

Perhaps the plot sounds familiar. Only this Midwest version of “When Harry Met Sally …” unfolded not on the silver screen, but on the University of Wisconsin-Stevens Point campus. Discover the many ways in which the love story of Jenna Kutcher ’10 and Drew Kutcher ’09 parallels the beloved rom-com’s screenplay—complete with a crucial New Year’s Eve scene, and the protagonists looking forward to their happily ever after.


Fate has a way of putting people in the right place at the right time. Of course, how quickly those people realize they are in such a situation, and whether or not they capitalize on it, is another matter altogether.

The back of a Comm 200 classroom on the UWSP campus turned out to be the right place for Jenna Shelerud and Drew Kutcher. The two took notice of each other pretty much right off the bat, albeit for slightly different reasons.

“To be completely honest, I thought Jenna was a ‘coastie’ the first time I met her,” confesses Wisconsin native Drew. “She was rocking yoga pants, big sunglasses, Ugg boots. But for real, Jenna had this positive energy about her and it drew people in, me included.”

For her part, Jenna—who, by virtue of being born and raised in Minnesota, was decidedly not a ‘coastie’—remembers thinking Drew was “cute, but not much more. Later that week I walked into the weight room and there he was, upstairs on a cardio machine. He smiled and waved at me.”

Because they were on similar academic paths and taking many of the same classes (in communications and business), Drew and Jenna kept running into each other. Since she had pegged Drew as a good student, Jenna decided to make the most of the  situation. “During that first semester I made him study with me,” she says. “We had an assignment to create mind maps on a topic, and I met him in the basement of May Roach to do it together. After creating those, I hung by his dorms and ended up schooling his guy friends on Guitar Hero.”

From such humble beginnings a close friendship was born. Jenna and Drew talked daily and confided in each other often, resumably even about the people each was dating.

As time went on, hints about what was to come started to surface.

After we were both single but best friends, we started joking that if we weren’t married by 30, we might as well marry each other,” Jenna says. “Then it turned into we had to kiss just once before he graduated, just to see what it would be like.”

With Drew’s graduation only a semester away, Jenna made good on what she calls their bet. “We were studying for an exam and then started watching ‘Home Alone,’ and I just went in for the kill,” she says of their first kiss. “That night I was giddy.”

Her euphoria turned to sadness when she realized she and Drew would be apart for a month over winter break, just as they were edging toward becoming a couple. Her sense of urgency became even more pronounced when she got into a car accident on her way back home to Duluth. After the accident, “I called him crying,” she says. “It was then that I realized I really loved him and I needed to seal the deal.”

When the two met halfway in Eau Claire around Christmas, Jenna made an impassioned plea that wound up coming off more like an ultimatum. “I told him either we needed to date or he had to let me go,” she says.

Drew admitted that he loved her but was afraid to move forward. “I told him that he couldn’t date me because we were the real deal,” she recalls, “and he knew that if we did date, we’d definitely get married.” Jenna headed for home without the matter reaching a definitive conclusion. But when she was less than halfway back to Duluth, she got a phone call from Drew, who said he couldn’t live without her.

A week later, Jenna booked a rental car and enlisted a friend to take a road trip to spend New Year’s Eve with Drew in Wisconsin. After toasting in the new year—multiple times—Drew asked Jenna to be his girlfriend.

The next day, however, it seemed as if his commitment to coupledom had gone the way of a hastily made resolution.

“I called him later that night and said, ‘It’s weird to say I have a boyfriend,’” says Jenna. “And he said, ‘Wait … what?’”

Apparently, bubbles from the free-flowing Champagne the night before had made Drew’s brain a little fuzzy; he didn’t remember asking her to make their relationship official. Jenna impetuously hung up on him, but Drew called back immediately and redeemed himself, proclaiming that he was glad to be her boyfriend.

“Let’s just say nothing is as romantic as those rom-coms we see on TV,” says Jenna when recounting the moment.

Drew’s marriage proposal in May 2010 was much more romantic. After Jenna’s graduation, Drew helped her move out of her off-campus apartment. He brought with him a hand-written list of 10 things they needed to do before leaving Stevens Point, including visiting the classroom where they had first met. The tenth item was taking a walk by the river, where he popped the question. It wasn’t until later that night, when they were celebrating their engagement with friends, that Jenna noticed the barely visible final item on the list, written in pale gray ink: “11. Get engaged.”

“All day I had been holding a piece of paper that told me what was coming and I never even saw it,” Jenna says.

The Kutchers were married on August 20, 2011. Four months earlier, Jenna had purchased a camera online. With no formal training, she started shooting weddings on the side, under the name Photos by Jenna Leigh. The business was both profitable and creatively fulfilling. She left a promising corporate career with Target, Inc. in 2012 to concentrate on her burgeoning business, with the couple’s income supplemented by Drew’s paycheck as a wine sales rep. The social media component of her startup soon took on a life of its own. Jenna started sharing her emarketing wisdom with other creative entrepreneurs through her Instagram account, speaking engagements and a wildly popular podcast called The Goal Digger. Today the company, now called simply Jenna Kutcher is thriving, boasting more than 200,000 followers across social media platforms, with 175,000 followers on Instagram alone. The venture has a very healthy bottom line, making Jenna a bona fide self-made millionaire.

In 2017, Jenna helped Drew launch @kickingitwithkutch on Instagram and The Kutcher Method, an online health, fitness and personal coaching venture. All the family businesses are based in their home, which will be moving from Wisconsin to Minnesota in March. Living and working together in relatively close quarters is not without its challenges. But the couple sets boundaries, and makes a point of respecting each other’s space and interests.

“Being good friends for three years in college helped us figure out what makes the other click,” notes Drew. “I’m a neat freak, she’s a messy dream chaser. I’m conservative and calculated, Jenna likes to gamble on the next big thing. We have great balance, and it just works for us.”

“We annoyingly still hold hands in the car, we dance in the kitchen and we cheer each other on,” says Jenna, “I’ve been waiting for the honeymoon phase to end, but we’re almost 10 years in and we’re still here, and in love.”