Diana May (Gagne) Connolly

PORTLAND – Diana May (Gagne) Connolly passed away unexpectedly on Feb. 6, 2020 following a brief illness. Her husband Robert was by her side.

Diana was born on Nov. 22, 1941 in Portland, the daughter of the late William Joseph Gagne and Doris Elizabeth (Munson) Gagne. She was a lifelong Portland resident, having been raised on Munjoy Hill, on both Kellogg and Sheridan streets. She attended Jack Junior school and was a graduate of Portland High School class of 1961.

It was in the same Munjoy Hill neighborhood that she met the love of her life in Robert “Bobby” Connolly. The two of them were inseparable and were soon married on October 21, 1967 at the Cathedral of the Immaculate Conception in Portland. In 2016 Diana and Bobby celebrated their 50th wedding anniversary in what was a grand, surprise event, surrounded by close family and friends.

She began her working career at Maine Bonding Insurance Company as a secretary and later transformed to a stay at home mom and housewife at the family home in East Deering. For many years, she continued working as a part-time bookkeeper at several Portland companies, including Friendly’s restaurant. As an added benefit to being home, she was able to provide after school care to many of the children that lived in the neighborhood. On any after school weeknight as many as 4 to 8 kids would be there doing homework or relaxing, waiting for their parents to arrive from work.

She was blessed to share a tremendous amount of time with her Gagne and Munson families. From Portland to Norridgewock, her aunts and uncles were numerous always around for any celebrations, cook-outs and reunions. Over the years she had the pleasure of living with her parents and both brothers, Billy and Larry, in their downstairs apartment of the family home.

Diana genuinely enjoyed a good chat and lively, often opinionated debate; all of which was held around her kitchen table. That same table would host; every birthday celebration, every Christmas dinner, countless Thanksgivings and various school projects. Most all of the conversations, news and plans were discussed there. It was truly her comfort space and her foundation.

She was deeply proud of her two sons and in the men they became and the families they created. It was a blessing to have them always nearby. She truly enjoyed using the power of motherly guilt by reminding her sons, in the corniest of ways, to always … “don’t forget to call your mother”.

Diane lived for her grandchildren; Meghan, Nolan Cameron and Vanessa. She gave them all of the love, and affection she had. Without hesitation, she cared for them preschool and post school and instilled in them all the proper values they would ever need. She enjoyed watching them in any endeavor they desired and was always present any games, plays and pageants. She also spoiled them in all the right ways and was thrilled whenever they called or visited.

She was beloved by her friends and family and loved them back. For decades, she and Bob rented a camp in August and many friends and family would come to visit. Whether it was Little Sebago, Watchic Lake or Bony Eagle Pond, it would quickly grow to become quite a tradition that moved through several generations. Later in life, her and Bobby would enjoy trips with the same friends and family to; the Caribbean, Ireland, Nova Scotia and Las Vegas. For many years, she and Bob loved taking long weekend trips to Booth Bay Harbor and visiting the local casino’s.

Diana loved music, loved to dance and enjoyed her white wine with ice cubes in it. She was a true family traditionalist and will be dearly missed.

She is predeceased by her parents, Mr. and Mrs. William and Doris Gagne; two brothers, William Guy Gagne and Lawrence Wade Gagne.

She is survived by her husband of 52 plus years Robert Martin Connolly Sr; sons, Robert Martin Connolly Jr., Kevin Barry Connolly and Kathryn; four grandchildren, Meghan, Nolan, Cameron and Vanessa; and many nieces and nephews.

Visiting Hours will be held from 4-7 p.m. on Tuesday, Feb. 11, 2020 at the Conroy-Tully Walker South Portland Chapel, 1024 Broadway, South Portland. A Celebration of Diana’s life will take place at 11 a.m. on Wednesday, Feb. 12, 2020 at the Funeral Home. Interment will follow at Calvary Cemetery, Broadway, South Portland. To view Diana’s memorial page or to share an online condolence, please visit www.ConroyTullyWalker.com.

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