When men and women date in their sixties and beyond there are typically differences in the approach that they take. Women often have a trusted friend or relative that they can turn to to obtain feedback about important decisions such as what to wear, how they look, and topics to discuss. Men frequently go it alone and without feedback they may be prone to making the same mistakes over and over.
Successful and confident people of both sexes probably do not need feedback to do well meeting new people and dating. Most people are a bit nervous and unsure about first dates and can benefit from a little constructive criticism. The quotation attributed to Albert Einstein certainly applies here. “The definition of insanity is doing the same thing over and over, but expecting a different result”. When men go out on first dates they often try the same strategy over and over and expect it to work in spite of past failures.
Try to open yourself up and confide in trusted peers to see what they think about your look and plans for a first date. You may gain some insight that will serve you well in your search for a new relationship.