Casual Dating

Tips for Older Men Looking for Younger Hookups

Woman Flirting with Man on the Street

If you’re reading this, you are probably 18 to 30 years old—about three quarters of guys dating online are! Even so, millions are looking for love and sex in every age group, and that includes a surprising number of older folks. Many seniors don’t feel like life is over after divorce or losing a spouse, and many have figured out the Internet is great for finding casual sex as well as longer term love.

You’ll see lots of articles about young men looking for a hookup experience with an older woman or “cougar.” But what if you’re an older guy who fantasizes about sex with a young woman?

Here are some tips if you are an older man looking for lust with a younger woman.

Know that It Is Possible

I have had many lovers who were much older than me, including a gentleman who was in his eighties! I genuinely loved him. The sex was very sweet. One of my girlfriends is dating a man forty years older! Some young women may have a thing for older guys, or they might simply be curious or open minded and find age irrelevant.

Be Up Front in Your Dating Profile

State what you are looking for unapologetically, and don’t lead people on. Some might think you’re a pervert or be turned off by the idea of dating an older gent—ignore them. You might not get a million responses, and you might get none for several weeks or longer. Be patient, and invest time and care into your dating profile regardless.

Highlight What You’re Offering

What’s in it for her? Figure that out, and make it part of your profile and conversations.

The most obvious thing that probably comes to your mind is money. The stereotypical younger-woman, older-man thing is the sugar baby, but I think both sides of this arrangement often want something else from each other—sex, affection, taboo, tenderness, intelligence, a learning experience, travel partner, companionship, romance, mystery… the list goes on.

A lot of young women grow tired of boys their age who might be rotten lovers or hit the bedroom all porny. Highlight that your casual encounters still mean taking your time. If you want the whole dinner date and wine thing before sex, that is still a selling point for some. If you have a Masters degree in art history or a passion for social justice, that can be important to girls who want real conversation with sex. Think about what it is you have to offer your date, and bring it forward.

Learn to Love the Internet

It can be difficult in a young person’s game to find the sex you’re seeking, but the Internet makes it more possible than any other option. Chances are, if you hit on a college sophomore at the shopping mall or a bar, you will strike out every time.

If you’re not already computer and smartphone savvy, you may want to learn the basics because the world of dating apps and niche sites are your best bets to meet younger women for hookups and more.

Be Personal and Specific when Chatting with Young Women You Desire

When you find a girl you connect with online, make sure your compliments and questions are specific to her unique personality. In other words, don’t talk vaguely about a woman’s beauty, but about the details of her photograph, her tastes, and style. Take it further, and ask about her aspirations, her interests, and her pets.

Even in casual sex encounters, women don’t want to feel interchangeable. If she has a fantasy about an older guy, or just happens to connect with you and is considering the possibility, you want to give her attention, respect, and compliments.

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Tell us what you think!

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