Maybe you used to be a great flirt, but how do you flirt with a man at this stage in life? When I suggest that to the over single women in my dating workshops . From awkward flirting mishaps to first date mistakes to avoid, bartenders have seen it all. Before dating apps became the norm, many people. To flirt with him in person, light touching, playful teasing, and sincere. the other girls he might consider dating — and you get to pick the perfect moment for you.