Rod Stewart and Penny Lancaster (27 years)
Rock and roll legend Rod Stewart met the much younger Penny Lancaster when he was already in his fifties. She was a photographer Stewart had hired to follow him on tour and take pictures to document the events. One thing led to another and the two soon became an inseparable couple. However, the pair actually did experience a split, but it only lasted two weeks before a reconciliation, something that Stewart is very thankful for. Stewart credits his ability to be a good listener for their twenty plus year relationship.