Roissy in DC has put together the two critical rules for older guys dating women under 25:

1. Don’t be needy
2. Don’t be insecure

Which to me both say the same thing: Don’t be an old letch! Admittedly, this is easier said than done. The reaction of an older man (30s-50s) who has caught the attention of a 20-something hottie is typically one of shock and awe. The older man becomes so enamored with his pretty young thing that he tries to hoard her for himself like a four-year-old and his favorite new toy.

From what I’ve seen, there is really only one rule for an older man dating a younger woman:

1. Be rich

Let’s face it, why else would a beautiful young woman waste her time with a dirty old fart, unless she has a daddy-fetish? But Roissy disagrees:

“The truth is that, contrary to the sugar daddy cultural message, money and a high status job are not required to attract younger women. They help, but what helps a lot more is tight game and a dominant, charming personality. If you are unfazed by the age difference, she will be too.”

The trouble with May-December relationships is usually not in bed, at least at first. The problem occurs once you move out of the bedroom and have to spend time together as friends. This is when you’re likely to find that you don’t share the same interests in music, movies, entertainment, sports, religion, politics and other activities.

It’s midnight and she wants to go out dancing, while the couch and Jay Leno look better to you. You’re debating the repeal of the Bush tax cuts, and she’s debating whether to get another tattoo near her bush. The sex may be hot, but often you will find the relationship is missing the cornerstone of friendship that’s essential for long-term love.

So my advice to the older man who finds himself dating the young woman of his dreams: Relax, and enjoy the ride while it lasts!

Top Two Rules for Dating Younger Women