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Be playful with her just like you would if you were close to her age. Play pranks on her, tease her, and just have fun when you’re around her. Having fun is a very important part of any relationship, but it is especially crucial when you are a good bit older than the woman you’re dating. 9. 6 reasons: Why A Younger Man is Attracted To An Older Woman. There are many reasons why a younger man may be attracted to an older woman. Here are six of the most common reasons: 1. Older women are more confident and comfortable in their own skin. They know what they want and aren’t afraid to go after it. I feel attracted to younger men. I am a 45 year old married woman. My husband is 49. We are married for the past 17 years. We have two sons. It’s been a good marriage. We are. Marrying a man who is much younger puts a certain amount of pressure on a woman. If a man, despite his young age, has leadership qualities, he will strive for leadership in relationships and this may cause problems. Plans for the future. Huge difficulties await a couple if they have a different view of the future together. 1. Be a flirt. If you are self-confident and self-assured, flirting should come naturally. Your knowing smile with a glint of mischief in your eyes will get the attention of that younger man. Younger women may also have more energy and enthusiasm, which lasts throughout the day and creates a more positive experience. 7. Men Hope That Younger Women Are More Sexually Adventurous A man who is looking for a woman to have a casual relationship with may be more attracted to younger women. Older women dating younger men may not be seen so kindly, although it could be explained differently. Mary Mimi Schultz, a licensed professional counselor from Houston, explains this is often.