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Little wonder his jaw fell to the floor when his wife hit him with the news that his internet 'conquest' was actually her, furiously tapping into her own laptop and raging as she read his suggestive responses.
Today, as the dust settles on their divorce papers, she is still angry.
Both gregarious and attractive, they were, says Steph, 'known as the perfect couple'.
But the fact that Simon had been in a long-term relationship before, only to walk out on his partner and a daughter from that union, should perhaps have made Steph a little less sure about his ability to be the perfect husband.
Steph and Simon's experience shows how dramatic the fallout can be.
The couple's wedding photograph, taken in 2002, highlights just what a handsome couple Simon and Steph Oldham were.
At several points he tried to arrange a meeting with his young admirer, clearly expecting a sexual encounter.
Steph had always wanted children, but parenthood hadn't happened for them.
In 2007, they turned to IVF and, to their great joy, in the following January Steph fell pregnant.
'I'd write them in text speak, or insert abbreviations.
I'd even add the odd spelling mistake, just to make it more authentic.' Well, Simon, 44, was certainly fooled.