He clung terrified to dad throughout a delightful production of Second Star to the Right, he bawled his eyes out for the first 20 minutes of The Jungle Book, and he screamed "I don't wanna go in theatre" as he was dragged into The Singing Mermaid.
So a trip to The Core at Corby Cube this weekend was the last chance salon as I was ready to give up, thinking that theatrical productions were only to the liking of his five-year-old brother.
Thankfully Dear Zoo changed all of that.
Perfectly pitched at toddlers, this adaptation of the best-selling lift-the-flap children's book was predictable, repetitive and reliable, just what my son needed to finally engage with the stage.
From the moment it started he sat wide eyed and agog, enchanted by the book coming to life.
Adapted by the author and illustrator Rod Campbell, it sticks firmly to the original 1982 story, but adds in three cheery characters in the shape of Sam the zoo keeper, Ben who is seeking a new pet, and his friend Sally.
The interactive production had both of my sons roaring, jumping and shouting as they met a host of inappropriate pets sent by the zoo.
The show mixes props, puppets and costumes to present everything from an elephant to a puppy and the impeccable cast never once drop their merry disposition (and I looked so hard to see their facade slip - it didn't).
Yes, the simple rhymes, repeated phrases and childlike chitchat are painfully inane for adults, but the show is not targeted at parents and nor should it be.
Instead this is a colourful, squeaky clean production that feels like it has leapt straight out of the television set from Cbeebies.
It is played safe and straight, and for little ones this works perfectly, particularly those age three or under. The tight running time of around 55 minutes also means that it is endurable for grownups and wriggly toddlers alike.
Thanks to this production my youngest son's fear of the theatre is now completely irradiated and next time I am sure he will be leaping into his seat.
Dear Zoo was performed at The Core at Corby Cube. It will be coming to The Lighthouse Theatre in Kettering later in the tour on Thursday May 31 and Friday June 1. For further details visit www.lighthousetheatre.co.uk.