First of all, thank you for such a long constructive reply. Also, I think you and your wife are absolutely right about honesty. Transparency in this situation would have prevented a lot of the trouble.

Funnily enough the first thing he said when I saw her photo was "see she's not even my type at all” and “ugly in real life". And even disclosed conversation between him and his friend where he was boasting about being approached but refused to share her photo because she's “ugly" - very alarming vocabulary to describe a woman and did not have the reassuring effect on me he thought it would.

In summary, he said he enjoyed someone showing interest and it boosted his ego. That it was something new and exciting until he felt bad for doing this behind my back.