How To Date In The 21st Century

Senior Dating

How to Date in the 21st Century

Nick Slade

Written by: Nick Slade

Nick Slade

Nick spent 20 years in the dating scene before marriage. He has always been the guy friends would come to for advice on relationships, and he developed a knack for giving helpful insights. After college, Nick was a disc jockey for a few years, when the love generation was still alive, so Nick has a lot of relevant experience to draw from when it comes to every aspect of dating, falling in love and screwing things up. He holds Bachelor's degree in humanities and a slew of master’s credits in journalism. Nick is a news junkie and tries to keep up on the latest non-fiction when he has time. He has published two books on how to win at dating and relationships.

Edited by: Lillian Castro

Lillian Castro

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A lot of things have changed since your first adventures with dating the ladies when JFK, Nixon or Reagan were in the white House — flying cars, weekend junkets to hotel casinos on the moon, world peace. Oh, wait, those fables of the future never happened. And you know what else? Human nature hasn’t changed one bit since then either.

To be sure, dating in the 21st century will not be exactly the same as it was a few decades ago. But, unless you pulled a Rip Van Winkle and have been asleep since Billie Jean King crushed Bobby Riggs in the 1973 “Battle of the Sexes,” you’ve been changing right along with the times.

Now, if you plan on dating college girls and 30-something gals, you definitely have some new challenges in store.

But, if you are interested in the ladies of your generation, give or take a decade, then you’ve all been riding in the same time machine, so no worries.

1. Finding women.

You might still swear by your four-on-the-floor transmission and your mechanical typewriter, but don’t underestimate the power of online dating. This is a powerful new technology, with online dating websites for seniors as well as mainstream sites.

You can browse through hundreds of profiles of single ladies from the comfort of your own Barcalounger, save the most compatible ones as your “favorites” and send them a message or chat with them live online. It’s easier said than done, so don’t be intimidated, a little trial and error never hurt.

Of course, if you want to meet them the old-fashioned way, you have to leave the house. If you haven’t been to a Sunday Mass or church service in a few years, give it a try. You could find a great lady (and even if you don’t, the experience might do you some good.)

Shopping, the gym, night classes or groups, volunteer activities, friends and relatives or just your old personal phone book are good places to find women who have become single again.

2. The approach.

One of the perks of age is you have learned to speak up, speak out and be relaxed and natural doing it. But instead of “Get off my lawn!” try something like “So, are you enjoying our beautiful day?”

Kidding aside, you have developed a natural charm and so has she. You both are not preoccupied with the presumed sexual overtones that made the approach awkward and terrifying when you were younger.

She is going to be more open to your approach on a human level, and you’re going to be, well, more human.

She’s still a girl but she is not going to be so suspicious of your motives, especially since you probably won’t be meeting her in a bar. Just string some words together and let your charm win her heart.


“It’s always going to be

about how you make her feel.”

3. The date.

She still feels ties and loyalties to her previous life, so keep it safe and low-key on the first few dates. You don’t even have to call them dates.

Find some daytime activities, like a walk in the park, a visit to the museum, a matinee movie or even a trip to the mall. Have an early dinner at a casual restaurant, offer to fix that door on her garage that she mentioned and wash her car, or invite her over to join you and some friends for your famous grilled burgers and chicken legs.

Especially if she hasn’t been dating for a while, it can be very intimidating for her to feel that she has to dress up and get her hair done for a date. Allow her to feel safe and relaxed, and all will be well.

4. Sex.

Life may have turned you more outward, making you a man of the world as you beat a path through the jungle of life and business. But it is very possible that her world was focused inward on home and family.

It may take a while for her to let you into the small but secure world that her life still revolves around.

When it comes to physical intimacy, you are really back at the high school sock hop with a big-eyed girl who wants to remain pure and good. Every woman is different of course, and some will be taking you by the hand to their room after a few dates.

But be prepared for the ones that need to start all over with hand-holding, a short kiss and a gradual journey to sweet abandonment in your arms.

Dating will always be dating, and girls will always be girls. The 21st century may have some fancier gizmos and gadgets, but for a woman, it is always going to be about how you make her feel.

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