Singer’s long-distance love ends in ‘I do again’

Leanne Pearson’s winding road to marital bliss leads to Nashville

Advertisement

Advertise with us

When Leanne Pearson flies, there is no doubt she chooses an aisle seat.

Read this article for free:


or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Hey there, time traveller!
This article was published 10/01/2024 (1001 days ago), so information in it may no longer be current.

When Leanne Pearson flies, there is no doubt she chooses an aisle seat.

If her latest single, I Do Again, is any indication, weddings and marriage are top of mind for the Winnipeg country singer and songwriter in the early days of 2024.

The tune, which came out New Year’s Eve, serves as a bit of a summary of the past four years for Pearson and her husband, Jordan Riley.

Their lives have been a whirlwind that began with their engagement in 2019; a separation caused by a closed Canada-U.S. border during the early months of the COVID-19 pandemic; eloping in Nashville for a ceremony officiated by an Elvis impersonator after reuniting in October 2022; and finally, a move back to Winnipeg and the birth of their son, Levi, Jan. 22, 2022, less than a month after Pearson was hospitalized with the coronavirus in Winnipeg.

The dream wedding ceremony and reception they had planned for 2020 finally became a reality this past October in Music City.

“It’s fun how everything has come around full circle,” Pearson says. “I ordered the wedding dress Oct. 31, 2019, and I picked it up almost a year later, September 2020, and I’ve been carting that thing around, through all of our moves, and I finally got to wear it in October.

“Three years later and after a baby it still fit, with only a few small alterations.”

COVID-19 was in their rear-view mirror, and little Levi, healthy, happy and about to turn two, served as their ring-bearer.

“We’re in such a beautiful time in our lives where we need to sit back and enjoy everything that has happened so far,” she says.

I Do Again is in a similar country-rock vein to the sound that has earned her four Manitoba Country Music Awards, most notably Album of the Year in 2019 for Pull it Off.

The outgoing singer hasn’t been shy about writing songs about her personal life, releasing the single Little Man while awaiting Levi’s arrival and Miles Away, a 2020 song detailing the anguish of long-distance love, when Pearson was in Winnipeg and Riley was in Nashville, waiting out the pandemic lockdown.

“I love to be able to write from my heart. I feel this is part two to Miles Away and Little Man, in that realm of ‘This is my love story, this is my life,’” Pearson says.

While many couples use popular tunes for their first dance as a married couple, Pearson found a different solution staring at her in the mirror.

“When I was looking for songs for our wedding, I couldn’t find songs that weren’t overused or (didn’t feel) old or stale, so I decided ‘Well I’m just going to write them.’ I decided to create what I couldn’t find,” says Pearson, who plans to compile those tracks for a future EP.

Supplied
                                Leanne Pearson and Jordan Riley were married in 
October in Music City.

Supplied

Leanne Pearson and Jordan Riley were married in October in Music City.

While she has learned some money-saving dos and stress-inducing don’ts of the wedding experience — both traditional nuptials and themed ceremonies — life’s curveballs have also made her knowledgeable about home renovations.

Her first experience with renos took place with high-profile assistance; she and Riley were part of a Property Brothers episode that had sibling hosts Jonathan and Drew Scott transform their fixer-upper in Nashville into a modern home that included space for a studio.

The pandemic hit and the couple chose to move to Winnipeg, so they used their newly gained knowledge to turn a Charleswood house into their new residence.

However, Pearson’s blooming country music career meant a return to Music City and another home renovation that had the singer serving as general contractor and social-media mentor to fans.

“Nashville was calling me back. I felt like I had so many things I wanted to accomplish I couldn’t do remotely from Winnipeg,” she says. “We learned so much that I ended up writing some blogs about it. I had a lot of people asking me, ‘How do I design my look on a budget? How can I do a reno quickly?’”

Alan.Small@winnipegfreepress.com

X: @AlanDSmall

Alan Small

Alan Small
Reporter

Alan Small was a journalist at the Free Press for more than 22 years in a variety of roles, the last being a reporter in the Arts and Life section.

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

Report Error Submit a Tip

More Stories

Sidney Crosby sings praises of Jets' Bjorck, summer training partner Barron

Ken Wiebe 6 minute read Preview

Sidney Crosby sings praises of Jets' Bjorck, summer training partner Barron

Ken Wiebe 6 minute read Monday, Oct. 5, 2026

PITTSBURGH — It wasn’t that long ago when the shoe was on the other foot for Sidney Crosby.

Read
Monday, Oct. 5, 2026

Letters, Oct. 7

6 minute read Preview

Letters, Oct. 7

6 minute read Updated: 8:08 AM CDT

Wally Daudrich apparently claims that Duff Roblin joined the PC Party in the 1960s. He does not know the history of the party.

Read
Updated: 8:08 AM CDT

Infill development on minds of all three River Heights-Fort Garry candidates

Joyanne Pursaga 4 minute read Preview

Infill development on minds of all three River Heights-Fort Garry candidates

Joyanne Pursaga 4 minute read Yesterday at 1:07 PM CDT

A trio of candidates will compete to become the first new city councillor in River Heights-Fort Garry since 2009.

Coun. John Orlikow, who won the seat in a byelection, is not running for another term.

Georgina Sabesky, who served as Orlikow’s executive assistant for 17 years, is now one of the candidates vying for the council seat.

Sabesky said that job gave her ample knowledge of the ward.

Read
Yesterday at 1:07 PM CDT

Man who exploited teen sentenced to 11 years in prison

Erik Pindera 4 minute read Preview

Man who exploited teen sentenced to 11 years in prison

Erik Pindera 4 minute read Yesterday at 2:00 AM CDT

A man who picked up a vulnerable 17-year-old child-welfare ward on the streets of Winnipeg and coerced her into providing sexual services for several months has been sent to prison for more than a decade.

After a trial, Hassan Kargbo, who’s in his early 30s, was found guilty of sexual exploitation, making child sexual abuse and exploitation material, receiving a material benefit from sexual services provided by a person under 18, procuring a person under 18 and advertising sexual services.

Provincial court Judge Julie Frederickson sentenced him to 11 years behind bars late last month.

“Mr. Kargbo picked up a young Indigenous girl walking over the Osborne Street bridge and quickly got her involved in drug use and escorting,” Frederickson said in a written decision.

Read
Yesterday at 2:00 AM CDT

Singer’s long-distance love ends in ‘I do again’

Alan Small 4 minute read Preview

Singer’s long-distance love ends in ‘I do again’

Alan Small 4 minute read Wednesday, Jan. 10, 2024

When Leanne Pearson flies, there is no doubt she chooses an aisle seat.

If her latest single, I Do Again, is any indication, weddings and marriage are top of mind for the Winnipeg country singer and songwriter in the early days of 2024.

The tune, which came out New Year’s Eve, serves as a bit of a summary of the past four years for Pearson and her husband, Jordan Riley.

Their lives have been a whirlwind that began with their engagement in 2019; a separation caused by a closed Canada-U.S. border during the early months of the COVID-19 pandemic; eloping in Nashville for a ceremony officiated by an Elvis impersonator after reuniting in October 2022; and finally, a move back to Winnipeg and the birth of their son, Levi, Jan. 22, 2022, less than a month after Pearson was hospitalized with the coronavirus in Winnipeg.

Read
Wednesday, Jan. 10, 2024

Estate of woman who died from local anesthetic injected into blood vessel sues Morden dentist, his business, clinic

Erik Pindera 4 minute read Preview

Estate of woman who died from local anesthetic injected into blood vessel sues Morden dentist, his business, clinic

Erik Pindera 4 minute read Monday, Oct. 5, 2026

The estate of a 23-year-old woman who died after receiving a local anesthetic during a wisdom tooth extraction at a Morden dental clinic has filed a lawsuit over her death.

Virginia Blatz never returned home after she went to Boundary Trails Dental Centre to have her wisdom teeth removed on Nov. 27, 2024. An autopsy later confirmed she died from local anesthetic systemic toxicity caused by an inadvertent injection into a blood vessel, her family has previously said.

Her father, Dulaney Blatz, filed a lawsuit in the Court of King’s Bench on behalf of her estate late last month, naming Ronald David Janz — the dentist who performed the procedure — his dental corporation and the dental corporation that operates the clinic as defendants.

None of the defendants have filed statements of defence in response to the claim, which has not yet been heard in court.

Read
Monday, Oct. 5, 2026