The Way We Were: Diane & Bill Pleasant

originally published May 2019

Written by Abigail Walker/photos courtesy of Diane Pleasant


When Bill Pleasant and Diane Roure’ met at a Belhaven University “get acquainted” party, it seemed they couldn’t be more different.

“I was a freshman music major, and he was a senior who played sports,” says Diane. “He liked country music, and I couldn’t stand country music. I liked to dance, and he didn’t.”

But the two soon realized they had a lot more in common than they thought. Both their fathers had served in the Air Force, so they had grown up traveling around the country. New York-native Diane had ended up in Greenwood, Mississippi, and Bill had settled in Jackson. They discovered that they also shared a Presbyterian faith.

“Our similar backgrounds were what drew us together,” says Diane.

For their first date, Bill took Diane to a lake. However, they each had a different idea of what a day on the water would be like. “He wanted to fish, but I was not interested at all. I wanted to swim,” says Diane.

Afterward, Diane says she hopped in the back of Bill’s truck so she could open a gate. But before she could jump back out, Bill took off with her in tow, honking and pointing to the girl in the bathing suit in the back of his truck. “I wanted everyone to see my catch,” jokes Bill.

Bill recalls another one of their dates when it was raining and he accidently caught Diane’s hairpiece with his umbrella. “It blew into a puddle, and I told him to go after it,” says Diane. “There’s never a dull moment with Bill Pleasant.”

Bill and Diane married on August 17, 1968, at First Presbyterian Church of Greenwood. They lived briefly in French Camp before spending 23 years in Jackson, where they raised their four children (Beth, Billy, Matthew, and Margie). In 1992, they moved to Clinton to be closer to their church, Providence Presbyterian.

“Having grown up with fathers in the Air Force, neither of us wanted to move around much,” says Diane.

Diane was a teacher in the Jackson Public Schools, and she also taught art and music at St. Paul and Mt. Salus schools. She is a member of the Arts Council of Clinton and has held several positions as a part of the Clinton Ink Slingers. She now teaches music at Morrison Heights Preschool.

Bill was a vice principal at Manhattan Council School, taught drivers ed in the Jackson Public Schools, and also worked in sales. “I still don’t know what I want to be when I grow up,” Bill says.

He now works part time at The Home Depot and runs his own handyman business where he says “no job is too small, but some jobs may be too big.” Diane says she loves to design projects for Bill to do around the house.

The Pleasant family is also a musically-talented one. Bill plays guitar; Diane plays a variety of instruments; their children play piano; and everyone sings. They once held a performance entitled “A Very Pleasant Evening,” in which the whole family, including some of their 12 grandchildren, participated.

This past August marked 50 years of marriage for Bill and Diane. Over 100 people attended the anniversary party given by their children and their spouses at Providence Presbyterian. Their daughter Margie made a cake, and their son Matthew created a slideshow of photographs. Bill played guitar and sang a song he had written for Diane, and Matthew and Margie performed a song that Diane had written called, “The Best is Yet to Come.”

One thing that Bill and Diane love to do together is travel. With family in Tennessee, Texas, and London, they spend a lot of time visiting loved ones. To celebrate 50 years, they will be heading to England, Italy, and Croatia.

“We went to New Mexico for our 25th anniversary because that’s where Bill wanted to go,” says Diane. “So now it’s my turn.”

In fact, when it comes to being married for as long as they have, Bill and Diane say it’s all about compromise. When they travel to New York City, which is quite often, they alternate between going to Diane’s choice of The Metropolitan Museum of Art and Bill’s choice of a New York Yankees game.

Though they might differ in opinion or interests, Diane says, “We always end up on the same side.”

“Which is usually her side,” adds Bill with a smile.

Their advice for other couples is to not expect everything to be perfect and to be patient with each other through the hard times.

“There will be bumps,” says Bill. “But we’ve been able to deal with that. We also credit our relationship with the Lord.”

“We both think we’re lucky to have each other because no one else would have us,” jokes Diane.

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A freelance writer from the Deep South with a love of reading, writing, dramatic storytelling, indie music, and her corgi pup.

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