Richard Madeley asked, "How can I ask out my postwoman without making things uncomfortable?

Richard Madeley asks out his postwoman without making things awkward. If he doesn't ask, he knows he won't get – but if she says no we both face the uncomfortable situation of seeing each other every working day. Richard asks: ‘How can I ask out my postwoman?’

As The Telegraph's Agony Uncle, I weigh in on your dilemmas – the good, the bad and the ugly. Richard Madeley weighs in on the good and the bad, the good or the ugly, as he weighs in with your dilemma. He offers his advice on how to approach the handsome man at work without upsetting your colleague.