How to Meet an Older Woman Online

Approaching older women online can be risky business for younger men.Approaching older women online can be risky business for younger men.

Let's face it; we are in the land of the cougar. A sitcom like "Cougar Town" with Courtney Cox has her playing a divorced mother getting back into dating, and finding that it's not the same for her as it is for older men. We also have daytime soap opera, where actor Caroline Hennesy, who portrays sexy lawyer Diane Miller on "General Hospital," is seen between the sheets with a younger actor. These characters are not only dating younger men and not apologizing for it, but are showcasing a trend that has younger men jumping to find out what dating older women is all about.

Dating via Internet

Introduce yourself properly.

Many women at 40 are starting to notice younger men are asking them out. But for the younger man, it may be hard to approach older women for fear of getting rejected by a soccer mom.

The Internet (and its dating websites) is the place to start to find these connections. You can pick out exactly what you want: hair color, race, gender, height, etc. So the problem is, how you should approach an older woman online so you can then move to first and second base without being turned away.

Learning simple step-by-step methods on your first contact, learning what women want to hear, and finally on to personal email, chat or getting a phone number, can give you the Internet advantage that most men can only dream about.

The opening email introduction letter is very important. Do not say, "What's Up" or "You're hot" on your first contact communication. You're trying to attract someone older, so think how they would want to be approached. Aim for sophistication.

Introduce yourself telling her why you are contacting her. Explain what caught your eye regarding her profile that would mesh with information about yourself.

Use humor to make inroads.

To break the ice, bring up some humor so the woman you are contacting will get a sense of who you are. After all, this is your first impression. Keep it light since you don't know her and you don't want to offend.

Ask about her. Use the opportunity to ask a question that you read about in her profile. This will let your potential date know you are really into her and want to find out more.

Picture please.

If you are contacting someone who has included a picture, and you don't include one of yourself, you are wasting your first email. Nothing puts off older woman more than having to ask for your photo. You want to see her, and you can be sure that she wants to see you.

Use words she understands.

Speak in a language she will understand. You are not texting your friends, so avoid IM speech. You should always capitalize when the rules apply. If you come off as texting, it may look like you are not smart enough for her to reply back. Texting can come later if she's comfortable with it.

Learn the differences between what younger women want, and what older women expect. Older women expect an introduction. They expect a picture of you. They expect someone interesting, fun and open. Understanding these simple steps should get you further along with an attractive older woman.

View Singles Near You

Click Here


  • Always be open and honest. Older women can smell deception a mile away.

About the Author

Adrienne Williams received her degree at Columbia College in communication design. She has 12 years of experience in technology and communications, six years in online publishing and Web writing, and publishes Tall Expression and Bi Social Network. She writes two columns for Examiner and has been published in the Huffington Post. She’s writing a book on the Enneagram and social advocacy causes regarding homelessness issues.

Cite this Article A tool to create a citation to reference this article Cite this Article