In the past, I flew with my old passport (and used the channel tunnel too). Having my new female one helped avoid a few explanations and made car hire in Slovenia easier though.
I did have a funny experience in Lisbon when we went to the baggage check-in for our flight back home. We handed over our passports but the woman at the desk didn’t seem to do anything. We asked if we should put our bags on the conveyor but she said she was waiting for the man to arrive. What man? we asked … the one in this passport she replied. It took a bit of doing to convince her it was me but she was ever so embarrassed and helpful after that. 🙂