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

By Emyli LovzMarch 9, 2019Strategy
dating after 50 for men

Look I’ll be straight with you; this is 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 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.

Define Your Goals

Before indiscriminately downloaded a bunch of dating apps, engage in a little reflection. 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 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

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. From 2013-2015 there was a 6% increase in 55-64-year-olds that used online dating. Both the young and older generations are becoming more receptive to online dating.

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 Match and eHarmony are percolating with single women ready to date a charming bachelor such as yourself.

We recommend signing up for 5 dating apps. No one dating application is alike. Each one targets a certain type of user. OkCupid will help you find a young partner while Elite Singles is used by a more educated and older crowd. Using multiple applications is casting a wide net. You’ll easily be able to meet people of all ages with varying personalities. 50 years ago you were likely to marry the person in the same apartment building as you were.

Yet with the help of dating applications you’ll be exposed to dozens of people with all kinds of backgrounds. The beauty of dating applications is that there really are no limits.

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. Classes 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 open new doors. Expanding your social circle means that eventually you’ll be exposed to other eligible single that you share a common interest with.

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’s some extra alternatives to online dating).

Dating After 50 for Men: Freshen Up Your Wardrobe

Has it been a while since you’ve worn something new? Perhaps you haven’t had much of a reason to invest in your wardrobe but times have changed. We tend to get complacent in lasting relationships. However, 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 have been muted through constant reuse.

If you despise shopping, as most men I know do – check out StitchFix for Men. My boyfriend uses this services and absolutely love it. This company ships you five pieces of new clothing right to your door. Keep what you like, return what you don’t. Here’s my referral code to get your first $25 of clothes at no charge.

Previous Relationships Are Approved Topics

When you were in your 20s, discussing an ex-girlfriend on a first date would have been considered taboo. But dating after 50 means that certain topics are open for discussion again. Obviously first dates aren’t the norm when you’ve reached a certain age. Most likely both parties will have interesting reasons for why they’re currently single. Broaching prior relationships that may or may not have worked out is a commonality you two share. Address what puts you two in the same boat and bond over your similarities.

Revel In The Chance To Date Again

Remember what it was like to have your adrenaline pumping as you meet up with that girl you met at the bowling alley on a first date? That feeling will come rushing back to you as you set out on our new romantic journey. Dating is a wild experience that will give you many novel and unforgettable experiences, both good and bad. Get excited about the romantic possibilities.

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

Don’t Settle

Yes. It’s true that the dating pool has shrunk 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 something 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. You should have spent enough time in a positive relationship to know what a negative one looks like. But in the off chance that this isn’t the case, hit the town and get to MegaDating.

Dating in Your 50’s As a Man: Dating Younger Women

Just because it’s unlikely that you’ll find the 30-year-old of your dreams doesn’t mean it won’t happen. You’re single again so why not date a younger woman if the chance presents itself? Before stepping out with a young vixen, there are some things you should keep in mind:

Don’t Play Mind Games

Surprised that a younger woman is interested in you? Don’t be. She’s chosen you over people her age because of your personality and experience. Callow mind games have made her leery of dating men her age. Instead she’s made the decision to spent time with a confident man that doesn’t feel the need to act like a child.

Don’t’ Make It Awkward

Do you think she’s unaware that she’s going out with an older man? One or two doubts passed through her mind before saying yes to seeing you but ultimately she made the decision to do so. There’s no need to exacerbate any awkward tension by making your age difference a topic of conversation. Just be proud that you’re splitting a bottle of wine with a charming woman and let those worries fade away. While dating you may receive some unwanted comments about going out with a younger woman. Learn how to deflect and recover from someone making the mistake of identifying you as her Dad instead of her boyfriend.

Get Hyped

Maybe going for a hike wasn’t the best choice for a first date. Naturally someone 15 or 20 years younger than you will have more energy. If you’re going to undertake dating a younger person be prepared to match their intensity.

Weed Out Gold Diggers

As much as older men dream of dating a young woman, young women dream of dating a wealthy man. This is the nature of dating. There are a couple steps that can be taken to filter old gold diggers. One is to implement the MegaDating philosophy and spend a grand total of no more than $10 on the first two dates combined. Gold diggers will surely swim for more lucrative waters if you refuse to splurge on the first couple dates. A second way to do this is to not list how much you’re worth (or your high ranking title) on dating applications. If such a question comes up on an app, leave it blank or find a way to keep it modest.


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.

There are a couple of rules that go along with MegaDating. I’ll share the key ones with you now.

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 allow for more time for you to date other people.

Second Date:

Third Date:

  • Night Time Setting
  • No Price Restrictions

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. 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 the best way to move forward.

If you’re ready to dive into the deep end of dating after 50, watch my webinar to learn more about my Signature Program. The program entails twelve private 50 minutes Skype coaching sessions with me over the course of three months, which breaks down to one session every week.

Throughout the program you’ll receive many benefits such as the revamping or creation of online dating profiles. In certain session we’ll meticulously craft messages to women that you’re attracted to, slowly turning you into a master online dater. We’ll also unpack the MegaDating philosophy in-depth. At the end of our time together, if you put the work in – you’ll have found a suitable relationship and/or reached the goals you set in our new client session.