SHELTON — When the curtain rises on Center Stage Theatre’s production of Man of La Mancha this weekend, it will be the fifth time in 15 years that Newtown’s Brett Boles, who will play Don Quixote, and Shelton’s Mia Scarpa, who will play Aldonza, have shared the stage together.

Their theatrical relationship began in the summer of 2000 when Scarpa, then a recent high school graduate, played Maria Von Trapp, and Boles, 14, played Friedrich Von Trapp, in The Sound of Music with the Youth CONNection, which is now a division of Center Stage. Two years later, the duo once again played mother and son on the stage in the group’s production of Children of Eden, with Scarpa as Eve and Boles as Abel.

“I was still a newcomer to theatre the first time I shared the stage with Mia in The Sound of Music and, immediately struck by her poise, I had complete confidence that she could shepherd all of us through the entire process,” said Boles. “Besides her professionalism, she also took it upon herself to care for each of the ‘Von Trapp’ kids off the stage, much as Maria does for them on stage.”

Seven years passed before the pair played on the stage again, as Scarpa was finishing her theatre degree at Muhlenberg College and Boles was beginning his degree in music composition at Ithaca College.

By the time Boles was out of college, Youth CONNection was now a part of a full-fledged theater, Center Stage, and opportunities for the pair to play opposite each other once more presented themselves. The first was a 2009 production of Cole Porter’s High Society, where Scarpa played the rich debutante Tracy Lord and Boles played C.K. Dexter-Haven, roles made famous in the 1956 film by Grace Kelley and Bing Crosby. Then in 2012, Boles and Scarpa played lovers again in the theatre group’s production of Guys and Dolls, with Boles as Sky Masterson and Scarpa as Sarah Brown.

Boles remarked about Scarpa: “Over the years, she became like an older sister to me, and I’m so glad we’ve had many opportunities since to share the same stage!”

The relationship didn’t end there. Boles, as a composer of musical theatre, would ask Scarpa to sing on demo tapes and try-outs in New York for shows he was writing.

“Brett is so unbelievably talented,” said Scarpa. “I always tell him he makes me look good, and he shows me unconditional support in everything I do, as I do for him.”

Now as Quixote and Aldonza, their relationship is a complex one. A mad knight, Quixote sees the world through rose colored glasses and places Aldonza on a pedestal, “seeing” her as a virginal lady whom he calls Dulcinea, and offering her a level of adoration and respect which she cannot handle and feels she doesn’t deserve.

Scarpa remarks: “What I love about the relationship between these two characters is that Aldonza is such a wounded, cynical person until she meets Quixote.  He helps her to heal the wounds of her past, because he does not judge her the way others do.  I can't imagine doing this role with anyone other than Brett.  I think in our many years of friendship, he has always seen the best in me on and off the stage.”

Boles added: “What I love most about the relationship between Quixote and Aldonza is that it doesn’t need to be defined by romantic love in the usual ‘musical theatre’ sense. Quixote sees beauty in her when she is unable to see it in herself, and that — to me — is the purest, most beautiful kind of love.”

Man of La Mancha opens January 30 at Center Stage and will continue weekends to February 15. Curtain will be Fridays and Saturdays at 8 pm; Sunday matinees at 2 pm; and on Thursday evening performance on February 12 at 7 pm.

Tickets are $ 25 for adults, $10 for students, and may be obtained by calling the box office at 203-225-6079 or visiting centerstageshelton.org.

The theater is at 54 Grove Street in Shelton.