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Dating After 60: 7 Rules for Men Who Want Love Again

By Emyli LovzJuly 18, 2019Strategy
dating after 60 rules for men

So you’re dating after 60 you don’t say?

I can wax poetic about how love doesn’t discriminate and all that cliché bologna but you wouldn’t be here if you didn’t already think the truisms about love were, well, true. You’re not here to be convinced that you’re worthy of love despite your age, but rather how to find it.

The dating scene has changed since you were last single. Decades may have passed, and in that short time the dating landscape has been splattered with apps, ghosting, gender equality, feminism, etc.


You’re not scared to dive into the single dating pool again. You just prefer to do so with a lifejacket on. As long as you’re willing to inch your way to the edge of the diving board, we’ll supply that lifejacket. I’ve coached romantics ages 18 to 72. Based on my coaching experience of all ages, here are seven dating after 60 rules for men. 

Dating After 60 Rules for Men #1: Don’t Dive In Until You’re Ready

Newly single men in their 20s get back into the field after a month or two of grieving. Adult men however, might need a bit longer to get back out there. Long-term loves are harder to let go than summer flings you had when you were 22.

Sometimes it isn’t just a partner that was lost but a lifestyle, social circle, and routine. You must be emotionally buoyant before jumping into the dating pool. Only when you’re comfortable, start taking baby steps towards the edge of the pool. Dip your toes in. If you feel the water’s too cold, take them out. The pool’s not going anywhere.

There’s an emotional aspect that might impede you from dating, but there’s also a personal one as well. Sacrifices are made when you’re in a relationship. Career, social, and personal goals might be put on hold because they don’t benefit the union.

When you’re married for decades it’s natural to let your goals fall by the wayside. But now that you’re a single man again, it’s time to dust off that bucket list and wet your pen. Learn how to rock climb, visit family in Italy, watch an EPL match at Wembley. For the first time in a long time you have the ability to make decisions without thinking of your wife and kids. Week-long fishing trip in the Outer Banks anyone? 

Rule #2: Don’t Forget To Spend Time With The Ones You Love

This may seem like an odd rule for an article pertaining to dating after 60. But look, dating isn’t everything. It doesn’t matter what age you are, finding someone to love should never mean neglecting friends and family.

Now that you’re single you have plenty of time to spend with friends and rebuild relationships. It seems odd that instead of hanging out with the kids and grandkids, you’re off meeting random women for the first time. Make sure there’s a balance between dating and family/friends. 

Rule #3: Get Active

This advice applies for those of all ages, but older singles might find breaking their routine to be tougher than when they were in their 20s. It can be easy to curl up and feel ensconced in your routine. But the best way to meet women at any age is to get out there.


You might be thinking so what. So what if I join a gym, sign up for a bocce ball league, or start playing trivia every Tuesday night at the local pub. No matter what I do I still won’t find a partner who’s right for me.

It’s true that there are less women available at 60 than when you were in college. But the times are changing. In 1990, 73% of adults ages 55-64 were married. But in 2016 that number dropped to 63%. Expect that number to keep dropping as marriage becomes even more normalized. Now that you know there are other singles out there, it’s time to find them. 

Meetup.com is a website than any senior single should join. There are a myriad of senior and non-senior groups that cater to singles. To clarify, Meetup.com isn’t a dating website. It’s merely a website that allows users to create and attend certain meetups. Meetup groups range from language groups, to archery, to senior singles groups. Remember that even if there aren’t singles in your group, you can always network. Befriend members and ask if they know of any singles worth introducing you to. Don’t think that your chances to meet another single your age rest solely on finding someone in a meetup group.

When you begin to brainstorm, there are hundreds of places to meet singles. Gyms, your friend’s party, charity events, bike competitions, the coffee shop, etc. Every time you step outside there’s a chance you’ll meet someone. All you have to do is put in the effort. 

Dating After 60 Rules for Men #4: Don’t Settle For The First Woman You Meet

We all have this fear. The fear that we won’t meet someone better than the person we’re dating, so we might as well stick with the person we’ve got. We think that the odds of us meeting someone better are too slim. Instead of casting our line out after having caught one fish, we take the only fish we’ve caught home and force ourselves to fall in love.

It’s tempting. I’m not going to push obvious lies on you and tell you that there are a ton of older singles out there. There aren’t. But that doesn’t mean you need to settle. What it means is that you need to figure out a way to combat the desire to settle on the first woman that gives you the eyes… but how?

MegaDating is the act of dating prolifically. It’s both a philosophy and a plan. Many men would be a proponent of dating a myriad of women in a short period of time. The reason we don’t see men do this is because they don’t know how. They don’t know where to find these women, how to get them interested enough to date them, or how to act once the date has begun. By following the MegaDating techniques you’ll be able to find a woman in her late 40’s or early 50’s that ignites the fire and keeps it lit in short time.

To understand the many nuances of MegaDating you’ll have to click here to watch my webinar. But to give you a glimpse of what MegaDating entails, I’ll provide you with the bare bones of the MD blueprint.

1st Date

Tapping various social streams will lead to a torrent of single women being found. To sift through these women without wasting time or money you’ll have to abide by the MD rules. As far as first dates are concerned they should not last longer than an hour or require more than $10 being used, even if you’re dating after 60. 


The thinking behind the restraints are that you shouldn’t be spending a copious amount of time or money on a stranger. Who knows if you two will end up hitting it off? A brief first date also means freeing up more time to date other women, thus decreasing the chances of burnout and increasing the odds of finding the woman that’s right for you.

2nd Date

Second dates should be active and free. Hiking, riding bikes or playing tennis is infinitely more enjoyable than staring at each other in a café. An active date also gives you more openings to physically touch with your date. As we well know, touch is the key to building intimacy.

3rd Date

Should she make it all the way to a third date, all date restrictions will be lifted. Feel free to spoil her with a fancy dinner, a trip to the theater, or whatever other awesome third date idea that pops in your mind. 

Rule #5: Don’t Hire A Matchmaker

Matchmakers have been around for centuries. But their longevity isn’t indicative of their skill. Matchmakers are great if you’re a lazy romantic. They sound nice in theory, but when it comes to finding the love of your life they often come up short. This is because matchmakers put you in contact with a select few bachelorettes from their limited dating pool. If nobody in their meager database fits the bill, tough luck.

Apart from having a limited singles pool to pull from, matchmakers have a bad wrap because of the lack of incentive they have in finding you a compatible mate. Most matchmakers are hired for 6 months to a year. Each month you’ll be introduced to a new suitor.

Yet many matchmakers won’t even set you up with a new suitor every month. If you ultimately hire a professional matchmaker, read the fine print. Ascertain that you’ll be set up with ‘x’ number of people every month.

So let’s say you are set up with two people a month. That sounds nice and all but that doesn’t necessarily mean that you’ll be compatible. In 2017, a woman looking for love filed a lawsuit against her matchmaker. After paying $150,000 for matchmaking services she was paired up with men that were described as “married, mentally unstable, or felons.

Here’s another good story about a NYC Matchmaker who was paid 100k to setup a client on 15 first dates over a period of 13 months, and completely failed. 


There is no guarantee that you’ll find a partner through matchmaking services. What’s worse is that after spending an exorbitant amount of money, you’ll come away with nothing. If you opt for a dating coach as opposed to a matchmaker you may not have a girlfriend by the end of the program (some do), but you’ll be equipped with the skills and dating strategy necessary to find women on your own. 

Rules #6: Stay Positive, Never Give Up On Love

It’s easy to get the blues as a single man in his 60s. You look around and it seems as though all your friends have their romantic lives figured out. You on the other hand may have just had your romantic world unravel with an unexpected end to your most recent relationship. To find a partner you’ll have to stay positive. There will plenty of uncomfortable moments while single. 

To make the most out of the experience, first strengthen your relationship with friends and family. When embarking on something so terrifying as dating after 60 it’s best to first shore up your emotional and social safety net first. This way it’ll be easier for you to sustain positivity.

As we age, we tend to lean on our partners for all our emotional needs. That just isn’t fair. Have friends and family sate some of your social needs before looking for a partner that serves as a friend, confidant, tennis partner, shoulder to cry on, etc.

Dating After 60 Rules for Men #7: If The Modern Dating World Confuses You, Hire A Dating Coach

You’ve noticed how jarring it is to switch from being in a relationship to single. It wouldn’t be so hard to make the transition if the dating landscape hadn’t changed so much since you were last single, but it has.

At the heart of it, dating isn’t that different from when you were in your 20s. Dates are all about meeting in person and building a connection. But when dating after 60 you might learn that finding women and progressing a relationship isn’t quite what it used to be. Nowadays if you don’t know how to use dating apps and sites you’re at a huge disadvantage. 

If you need a little help navigating the dating world, ask for a helping hand. As a dating coach, I’ll be your professional wingwoman. The biggest hurdle you’ll need to jump over is figuring out how to find single women. In my 3-month Signature Program you’ll learn how to effectively use MegaDating to tape social channels in order to find eligible women. I’ll teach you how to plan successful first, second, and third dates. I’ll show you how to effectively message on dating apps, build sexual tension in person, and everything in between and after.

To get started, book a New Client 1-on-1 Skype session and we’ll begin sculpting a dating plan that works for you.