10 Tips for Younger Men Wanting to Date Older Women

single older woman
  • DatingRing
  • Feb 9, 2023

Are you looking to date an older woman? You’re not alone—a lot of men are looking for cougars, or simply feel more comfortable around older women. In turn, older women are usually more comfortable in themselves as they have more life experience!

If you are a younger man wanting to date an older woman, here are some tips for you!

#1 Don’t Play Games

Older women are over flaky men who cancel last minute, don’t show up to dates, and take three days to answer a text. Live your life—until you get into a serious relationship your current life should be more important than someone you just met—but don’t act hard to get. Simply fill your life with enough interesting experiences not to sit by the phone all day waiting for the next text.

Women want men who prioritize themselves, but not men who play games. They want men who know what they want and go get it.

#2 Develop Real Confidence

In our younger years we tend to confuse ego with confidence. Real confidence is knowing you can handle whatever life throws you. Confidence means you dare to go for what you want, because you know you’ll be OK even if you fail. Confidence is also about feeling comfortable in your own skin, because you act with integrity—you stay true to your ideals.

Ego confidence, on either hand, is thinking your worth is about how much money you make, how many women you’ve slept with, and so forth. In essence, your confidence is based solely on achievements.

Confidence is sexy and older women generally know the difference between ego confidence and real confidence.

#3 Be Clear About Your Expectations

Be up front about what you’re looking for—casual dating, a relationship, or whatever it may be. No hidden intentions.

#4 Learn to Speak Your Mind in a Respectful Manner

The older women get, the less shit they take. They also know there will be disagreements in all relationships. So learn to communicate in respectful manner—articulate your truth without blame and take responsibility for your own emotions.

Stonewalling, temper tantrums and passive aggressive behavior are all signs of immaturity.

#5 Show Kindness

Older women have seen enough in life to appreciate kindness. This could be seeing your consider other people around you and, also, consider the woman you date. Small things like pouring a cup of tea or cooking a meal after a long day, for example.

There are a lot of people who aren’t kind, so the older you get the more you tend to appreciate those who are.

#6 Don’t Turn Her Into Your Mother

She may be kind and caring and know how to cook a decent meal, but she isn’t going to do your laundry, or wash your dishes unless you do the same for her. And while she may be able to mentor you in some ways, she won’t take responsibility for you. She wants a man who is independent and can live his own life. In short, don’t become dependent on the women you look to date.

#7 Learn How to Flirt and Take a Genuine Interest

Banter is sexy. “Hey, you wanna come over?” is not. Learn to flirt and have fun with it. A man who can balance showing a genuine interest by asking interesting question about his date and engaging in deep conversation, while also being able to flirt and have a laugh is a real winner.

#8 Compliment Freely

An older woman will want to know you genuinely find her attractive - inside and out. So remember to compliment her looks, what you find sexy about her, and her personality.

An older woman may well feel insecure about whether she has what it takes to satisfy you in the long run - after all, she won’t have the same body women your age do. So be sure to tell her what you like about her and keep doing so once you are in a relationship. We all tend to forget the compliments after dating someone for a while, even though that’s when they’re needed the most!

#9 Learn About Relationships

You may be in your forties dating someone in her fifties or sixties. Then chances are you have plenty of experience with women and relationships, but if you don’t—read books. Even if you do have experience, reading books or listening to audiobooks about relationships will help you grow and evolve. Remember that if a relationships grows stagnant, it dies. Keep learning. Keep growing. Keep making things even better.

#10 Create a Life You Love

Whether you date someone your age, or someone who is older, or younger, having a life you love is sexy. Fill your diary with things you enjoy doing. Keep learning and growing and stepping out of your comfort zone, too.