What Scares Rich Older Men the Most (and How You Can Get Around It)

We tend to assume a lot of the time that all older, rich men dating, or at least trying to date, have no problem approaching a young, beautiful woman—isn’t it in their nature? But it turns out that the prospect of dating can sometimes be a scary thing for many older men, especially if they’re a single dad or divorced.

A recent survey asked roughly 500 men between the ages of 35 and 55 who earn a six-figure income (at least $100,000.00) about their biggest dating fears. More than half of the older men (54%) admitted that they usually struggle when meeting a woman in person for the first time, and the most common reason was that they didn’t know how to start a decent conversation with her. The second most popular rich men dating fear was that they didn’t know how to go about approaching a woman who was with her friends, followed by feeling intimidated by a beautiful woman’s appearance.

This shows that a lot of rich men dating, no matter how suave they appear to be, still have some reservations when it comes to playing the dating game. If you’re trying to meet rich men and you spot an older man who looks interested, there are a few things you can do to help make it easier for both of you:

• If you’re with a group, break away from the pack—an older man will be more comfortable approaching you when you’re solo.

• Use your surroundings to start a conversation with an older man you’re interested in. In other words, look for something to talk about. If you’re at a restaurant, ask him what dish he would recommend. If you’re at the bar, tell him you love the music. If you’re at a wedding, ask how he knows the bride and groom.

• If you make eye contact with an older man that you’re interested in, give him a subtle smile. Don’t flash him a wide grin—that’s a little creepy—just a little flirty smirk so that he knows you noticed him. Playing hard to get can sometimes backfire in the dating game, especially if he’s already struggling to make the first move.

• You want to look primped, but not too high-maintenance. Dress for the occasion—if you’re going to a casual bar, leave the six-inch stilettos and mini sequined dress at home.

What do you think: Do you have any other good dating tips to help meet rich men?


“New Survey Reveals Men’s* Biggest Dating Fears,” PR Newswire web site, October 1, 2013; http://goo.gl/IUt2Sw.



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