8 Old-Fashioned Dating Rules to Stop Following After 40



Given the explosion in dating apps—and cultural phenomena such as the #metoo movement—the rules of courtship today are changing in real time. And if you’re over 40 and re-entering the dating pool after a long absence, you might find the new reality jarring—and that many of the things once considered “romantic” are now seen as “creepy.”

To make sure that doesn’t happen to you, here we’ve compiled all of the wildly dated and totally old-fashioned dating rules that once were great but today you should avoid at all costs. So read on—and happy dating! And to learn all of the seemingly dated but still relevant rules of courtship, check out 40 Old-Fashioned Relationship Tips That Still Apply Today.

It’s Helpful to Play Hard to Get


Back in the day, women were taught that if they really wanted to hook a man’s attention, they should turn down his first few attempts to secure a date in order to make the man feel victorious when he finally gets a “yes.”

But this is actually terrible advice, because it makes it seem like courtship is a battlefield in which men are knights and women are conquests, and sends men mixed signals about whether or not “no” actually means “no.” And for more on this, learn Why Your Days of Playing Hard to Get Should Be Numbered.

If She’s Not Interested, Try Harder


Just as women were taught to be coy, men were taught that if a woman turns you down, you should just try harder to woo her affection. It’s worth noting—again—that if a woman turns you down, you should just accept the rejection and move on. And if a woman does later tell you that you should have just “tried harder,” feel free to remind her that it’s 2018.

Men Need to Always Make the First Move


Not only is it no longer taboo for women to ask a man out or send the first text,  And it’s not just Millennials who feel this way either. And for more on this, see how this New Study Says Older Men Want Women to Make the First Move.

Dating Apps Are for Losers Who Can’t Find Love


There are a lot of ways in which the apps have made the dating landscape more challenging, especially for women. But there’s also research to indicate that it’s been beneficial to people in older age groups, who might not be as comfortable scouting for a partner in a bar

Either way, we’ve come a long way from the days when it was so embarrassing to have a Match.com account, and there’s certainly no stigma to meeting someone on the Internet. Give it a try! And for the best options, check out The Best Dating Apps if You’re Over 40.

The Man Needs to Pick You Up for the Date


There’s nothing wrong with picking a woman up in your sweet Chevrolet for your night on the town. But, equally, there’s nothing wrong with a woman picking a man up for the date either. In 2018, it’s totally fine to just meet at the restaurant.

You Need to Get Super Dressed Up for Your Date


You don’t want to look like you rolled out of bed and into a hamper, but wearing a three-piece suit and a feathered hat might make it look like you’re trying too hard. (Well, unless you’re Ryan Gosling, who gets a pass.)

The Man Should Pay the Bill


In 2018, it’s customary to go dutch. In fact, some women today may insist on splitting things evenly, because allowing a man to pay makes them feel like he’s expecting something more.

Now, let’s be clear: there’s nothing wrong with being old-school, and some women think it’s a nice gesture when a guy does pick up the bill, so there’s no harm in offering to pay. Just be mindful of your date’s reaction and comfort levels.

My tip: If you’re a man, offer to pay, but say say, “You can get the next one,” which serves three purposes: you feel like a gentleman,  you’re indicating that there will be date two, and she won’t feel like you’re simply angling for a one-night-stand. And for more great dating advice, check out the 40 Things No One Tells You About Being Single After 40.

Always Bring Flowers

There’s nothing inherently sexist about bringing flowers to a date, and some women would still find the gesture sweet and romantic. But it’s definitely become very outdated outside of Valentine’s Day, and it’s worth knowing that a lot of women find it overeager and weird.


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