Skip to content

Dating After 50 for Men: Tips and Strategies For Getting Back Out There

Dating After 50 for Men: Tips and Strategies For Getting Back Out There

Look I’ll be straight with you; things are going to get weird.

Chances are you haven’t gone on a first date in possibly decades.

As you can imagine the dating scene has changed a little since you hung up your Friday night polo and tucked your all-denim outfit in the back of the closet.

Technology has morphed the way we date, but even if dating applications were taken out of the equation, dating in your 50s as a man would still be drastically different than it was when you were 25. Luckily, the core idea is the same; form a romantic bond with the person sitting across from you. This is a skill that surely your millennial dating peers are lacking.

Use your interpersonal experience to your advantage as you traverse the new dating terrain. Although it may seem odd getting back out there, your experience makes you more prepared than you were in your 20s. Pair the knowledge you’ve accrued over the years with these tips and strategies to ready yourself for dating after 50.

Dating After 50 Tips for Men

Define Your Goals

Before indiscriminately downloaded a bunch of dating apps, engage in a little reflection. If it’s been a while since you’ve woken up a single man, ask yourself what you want romantically.

Is it immediate companionship that you’re seeking or is playing the field for a while a more appealing option? Knowing what you want from dating will make choosing the route towards accomplishing your goals more obvious.

Whatever your ultimate goal may be, MegaDating will help you achieve it. MegaDating is simply the exercise of dating a lot of people within a short period of time.

Doing so will expose you to a number of personalities and will quickly make you realize who’s right for you. Going on a bunch of dates in quick succession will also mitigate any fear you have associated with dating.

Set Your Expectations

Any man that’s dating after 50 would love to happen upon a single 35-year-old woman with no kids. But some things just aren’t meant to be. While this may be ideal, it’s not very likely.

Be realistic about your options. If you’re deadset on meeting someone 15+ years your junior, then be willing to cast your rod in the water and rarely ever get a bite.

Also realize that to score dates you’ll have to put yourself out there. Be prepared to get acquainted with dating applications and expand your social circle.

Investing the time into messaging people on dating applications and joining social groups are the steps you need to take in order to find a romantic partner.

Adapt Or Flounder – 50 And Older Dating

Want to know the best dating advice for men over 50 that I can offer?

Start dating online.

It turns out that 40% of Americans use or have used online dating.

But the legions of online lovers that are clicking away at their phones aren’t limited to 20 somethings. Over a fifth of those aged 55 and older have at one point used dating apps.

But look I know what you’re thinking. Dating again is weird enough but adding the twist of meeting people online is just too much. The truth is that hitting the bars or meeting other singles through mutual friends is time-consuming and only offers so many options.

Meanwhile, online dating applications and websites like Bumble, Hinge, and Our Time are percolating with single women ready to date a charming bachelor such as yourself.

The top five apps we recommend all singles dating over 50 in urban areas to sign up for are:

1. Hinge

2. Bumble

3. Silver Singles

4. OurTime

5. FB Dating

Downloading all five ensures that you’ll interact with an array of people and that your new flame doesn’t slip by unnoticed.

A Word On Dating App Filters

If you only try and match with women who are significantly younger than you, you may run the risk of harming your ELO score.

An ELO score is the algorithm most dating apps use to assess your market value.

If you’re only looking for women who are much younger (and you set your filters say to only match you with women who are 25-38 and you’re over 50), you’re not going to get many swipes right.

You’re now competing against a pool of younger, more age-appropriate men. 

The fewer right swipes you get, the lower your ELO score becomes and the less desirable people the dating apps are going to match you up with.

For this reason, I recommend setting your age filters to 10 years younger to 10 years older and ONLY swiping on women you would consider going on a date with.

If you want to go younger than that, make sure you also widen the age range to 10 years older.

It doesn’t mean you have to date women who are older, but you’ll win more right swipes which will increase your market value on the app and show you to more women who are of higher quality.

NEVER swipe right on women you wouldn’t date or you’ll train the apps to send you more of these women.

A Pause For Some Good News

You may not feel it, but you’ve never been so popular before.

According to Statistica (and every other publication out there) as we age women begin to outnumber men.

dating in your 50s as a man

While your options have shrunk, without you knowing so has your competition.

It’s never been so easy to catch the eye of a single woman.

That’s in part because there are simply fewer men to go around. 

You’re a hot item and will get even hotter as you age.

Start Taking Yoga, Gymnastics, or Adult Education Classes

Here’s an opportunity for you to kill two birds with one stone.

You’ve been wanting to learn Spanish for ages. Now you have the added incentive to do so. Group classes –regardless of romantic language or activity– are great ways to meet new people.

Don’t think that you’re limited to just the people that sign up for your 3-month dance class.

Making connections in class will lead to connections being made outside the classroom doors as well.

Expanding your social circle means that eventually you’ll be exposed to other eligible singles that share a common interest.

If you’re not a fan of dating applications this is the perfect way to meet people without having to learn the ins and outs of online dating (here are some extra alternatives to online dating).

Meet Women By Volunteering – Dating Advice For Men Over 50

Women who make time to give back to their communities are thoughtful, kind, caring, humble, and loving.

Am I missing any adjectives you would use to describe your ideal partner?

Meeting women through volunteering easily weeds out gold-diggers and selfish women.

Learning how to start dating again after 50 is all about learning where to meet single women your age. Volunteering events are known to attract an older, generally speaking, more female crowd. 

Freshen Up Your Wardrobe

Are you about as much of a fashionista as Dwight Shrute?

Perhaps you haven’t had much of a reason to invest in your wardrobe but times have changed.

That habit of not going above and beyond must be done away with when meeting new women. I’m not saying you need to head to Nordstrom’s and max out a credit card.

Just be sure that you possess articles of clothing that still have enough life in them to make you look good.

If you despise shopping, as most men I know do – check out StitchFix for Men. My boyfriend uses this service and absolutely loves it.

This company ships you five pieces of new clothing right to your door. You just need to give them your preferences and they’ll do the rest.

Keep what you like, return what you don’t.

Here’s my referral code to get your first $25 of clothes at no charge.

Revel In The Chance To Date Again

You’re being presented with the opportunity to significantly change your life for the better.

Grab on to the reigns and push forward into unchartered territory. Embrace the newness of the experience and realize that the person sitting on the other side of the table is just as nervous as you are.

If you’re afraid of an endless stream of mediocre coffee dates, propose that you and your date accelerate your bond by doing something that you have on your bucket list.

This ensures that the encounter is compelling and even if you’re not into your date you’ll still reap enjoyment from the activity at hand.

Don’t Settle

It’s true that the dating pool has become shallower over the years.

There aren’t as many eligible women that you’re interested in as there used to be. But that doesn’t mean that there isn’t someone amazing out there for you.

Having found someone to pass the time with is comforting, but don’t lock down the first person that expresses an interest in you. After logging in to any online dating application you’ll see that there are a myriad of options out there.

Dating various women –or MegaDating- will mitigate your desire to settle. By dating multiple women you’ll see that there are options out there. You’ll also get a feeling of your likes and dislikes.

MegaDating is all about dating various women at the same time. The purpose of this is to swiftly find a compatible partner as quickly as possible.

To find eligible women you’ll leverage social channels.

These channels might include:

  • Dating apps
  • Parties
  • Friends
  • Acquaintance social circles
  • Parents of your children’s friends
  • Gym
  • Group classes
  • PTA functions

Once you meet a compatible woman you’ll need to ask her out efficiently by using a TDL.

After she agrees, it’s time to go on a date.

But how do you imagine you’ll be able to realistically date various women at the same time?

It’s all about the types of dates you go on.

Men feel the urge to pay $100 and go to some fancy restaurant on a first date.

That’s not what I advise.

Keep reading (or watching) to learn how date various women simultaneously without breaking the bank.

Don’t Be Taken Advantage Of

A 2019 study from the journal of Social Psychological and Personality Science found that between 22-33% of women have accepted a date request for the sole reason that they’d receive a free meal.

For these women, it’s not a date but a “foodie call” as the researchers named the dynamic.

It should come as no surprise that unscrupulous younger women would agree to see you just for the opportunity to eat a free meal.

They know you have money and would happily pay for their $35 steak.

Younger women are much more likely than women closer to your age to use you from your wealth and connections. It’s unsettling but be aware that there are women out there.

However, there is a way to filter these women out.

It’s called MegaDating.


This dating philosophy has been touched on throughout the article but warrants a more intimate look.

As you already know, MegaDating is the act of dating prolifically. It doesn’t matter how you meet these women –whether online or IRL- the chief point is that you’re going on a lot of dates.

Men dating after 50 might feel as though the dating pool is shallow. Effectively leveraging MegaDating strategies will quickly show you there are plenty of compatible women out there.

With the goal of cutting down the time it takes to meet a worthy long-term partner, there are some rules you need to abide by if you’re going to date efficiently.

First Date:

  • $10 or Less
  • 60 Minutes or Less

The reason for not investing too much time or money on first dates is that in reality you’re going on a date with a stranger. You have no idea if this person is even worth spending 10 minutes of your time with. Making dates short will help avoid date burnout and free up more time for you to date other people.

Second Date:

If they’ve made it to a second date you obviously see something in them.

Continue to cultivate this flame by enjoying an active second date together (yoga, biking, hiking). Accelerate the bond and create sexual tension by engaging in physical contact. If you’re worried about awkward touching, read this anti-awkward guide on romantic physical contact.

Third Date:

  • Night Time Setting
  • No Price Restrictions

She may have been skeptical of your affection after the first two dates.

You two may have not spent much time or money together.

This won’t be the case on a third date.

If she’s landed herself a third date it means that you’re into her. Seeing as how you’re MegaDating and have plenty of romantic options you wouldn’t waste your time dating a woman you’re not into three times.

Show her how much you’re into her by going on a fancy date that sweeps her off her feet. No more financial or time restrictions for this one.

Learn How To Start Dating Again After 50

To understand how the many nuances and benefits of MegaDating will help your dating skills let’s chat.

I realize that a dating coach might be a little weird for you but so is dating after 50 (or even after 60).

Don’t take on this new experience alone.

Let’s talk about your worries, dating background, and goals via a 1-on-1 New Client Skype Session so that we can determine if our dating program is right for you. 

Comments are closed for this article!

Featured Articles