Dating at 40, 50 and 60+

May 16, 2017 - 16 minutes read

Dating at 40, 50 and 60+

Senior dating can seem as intimidating as finding love after 40. It can seem tricky, as you’ve so many added pressures, but through popular dating sites and singles sites and in the real world it is never too late to find love and real companionship.

Instead of the usual breakdown of tips, I’m going to highlight what makes approaching each decade different and how to manage each decade. You might be over 50, but you’re not over the hill, and there’s plenty you can do to render yourself an eligible bachelor again.

You may not have to look in the same kinds of places, and you may be after a different type of woman – you’d may like to meet older women with whom to build trust and companionship – but there are still some unfaltering fundamentals to approaching women that resonate at any age.

What to keep in your arsenal at all times

You may be over 50 dating once again, but some things don’t change. Women around menopause time may be hitting low confidence and rethinking their entire body, so there’s even more need to be as proactive as you would in a club. Dating for seniors does not mean limiting your options: in fact, between 40 and 70 there are so many complicating factors like family and poor health that you have to cast a wide net.

You may also have been through some gritty stuff, and some older men have the tendency to hermit themselves a little, working so hard during the week that you just want to curl up in front of the Darts on a Sunday. But you have to continue investing in yourself – keep up your hobbies, reconnect with what you enjoyed when you were younger, get out of the house and stay active. This applies at any age, but don’t lose sight of it – it’s what makes “you”, your product, unique. If you’re 40 dating again or over 50, you have to be sure to show you still have a lust for life.

Make sure your conversations are reactive and be sure to let the stubbornness go. Stand by your views – as senior singles, the advantage you have over younger daters is that you’ll have stronger convictions. Don’t hide them away. But also learn to listen. You’ll have 20 or 30 more years of backstory to get through. It’s especially important as you may be following in the wake of failed marriages, family deaths, even bereaved partners.

Not only will keen listening help you understand the framework in which you’re operating, but also as someone past their physical peak will display your mastery of conversation. That has always been important, and remains crucial for single men over 40.

Now I’m going to look at how you’d adapt to dating after 40.


They say life begins at 40, but dating at 40 and above is a tough transition. Those who are still single at 40 (and, indeed, those who are married or in long-term relationships) will be going through an existential reassessment of who they are. It comes with a lot of insecurity and baggage.

40 and single does not mean you failed; it means that circumstance has led you into a field of opportunities again. Dating in your 40s gives you a great opportunity to stand out from a sea of self-pity.

Be positive and stand out

Keep yourself dressing smart and thinking positively – maybe get a younger relative or female friend to help redesign your wardrobe with what they’d like to see. Get a flattering, realistic haircut (i.e. don’t try too hard and look like you’re hiding something) and avoid dwelling on the past.

I know that’s easier said than done, and you’ve no doubt got a lot of past behind you if you’re over 40 dating. You’re still statistically only halfway through your life. if you’re looking for another chance at finding love after 40, you have to be in a position to do so mentally.

Deal with any overriding personal issues and then relax and enjoy the process of dating. If you approach dates with single women over 40 with positivity, and a smiling demeanour, you’ll have an edge over most dates she’s been on.

You don’t have to be on a Buddhist plane of zen-like calm. Just leave your baggage behind before you head into a world of potential new life partners. It’ll make you so much more attractive than the stereotype of 40 somethings would have you believe, and it’ll be way better for you in the long run.

These could be online dating tips for women too – it’s a simple part of having more life experience and meeting new people.

Online dating

If you’re more advanced in your career, you might consider using an over 40 dating site. There are plenty of sites for professional singles over 40, and as long as your you’re researching the dating sites’ reviews you should be able to find some great matches.

An example of this is Our Time Dating ( a very handy service that comes with an app. It’s one of the leading specialised mature singles websites, so you can invest a lot of time in crafting a profile and narrowing your searches.

There’s a world outside of the Our Time dating site, you just have to search around and find one that you really want – some of the best free online dating sites are eHarmony and plentyoffish, and if you want to put money into it there’s a whole article about it [link to Dating agencies article.] Generally, the best online dating sites are the ones you pay for.

I’m going to give you a list of the best dating sites for over 50 and over 60 year olds a bit later, because

Just make sure you pick a site that fits you, as so those are the best dating sites for women that fit with you.

Your 4th decade is handling the concept of old age gracefully. Now for entering it…


Give off success.

At 50, a woman wants to know you have ownership of something. If you’re over 50 dating, you should be in a position to save funds for your future. You should be at the apex of your professional career. You should at least have something that you’re proud of before dating over 50.

It becomes much more important to carry that success. Make sure you don’t lose your posture, stretch everyday to fend off the arched back that can come with progressing years, and dress relaxed but smart.


Dating for seniors is not just about looking back, but forward, to a fruitful relationship. You need to show her that she has something to look forward to.

Go and see shows, or have dinner – don’t forget to go on actual dates. Miss a few bedtimes. Break your routine for her. Go on holiday every few months, even if it’s within the country. Show her that you’ve been working most of your life for a reason, and make her feel like the reason. Learn to filter out the noise of mature adult life and look forward to spending time together, and the future at large.

And, as above, search for good dating sites and find the best dating site for you. Don’t rely on date sites though. Be active and get about – go to museums, walk in the park, maybe go see the reunion of a band you used to love. You’ll have instant common ground with any women you talk to, and a great icebreaker.


When you’re out in the field or on senior dating sites, humour is vital. And not just firing off dad-puns left right and centre – it comes off as a sign of insecurity. One thing singles over 50 seek is companionship, and the ability to joke around and riff off each other plays a central role in that.

So stay reactive in your humour, try not to go on frustrating, long-winded and self-deprecating joke reels. React to what she’s saying, comment on what she’s talking about. If you’re online dating over 50, make sure your first date is something in which you can talk to others at some point – like going to see a show, and cracking people up in the foyer.

At 50, it’s important to show that your mind is still sharp and that you still have social currency. Showing you can make her laugh, and other people laugh, will give you some heft.


Online dating

Forming a connection first can be pretty important at 60, and as with any decade, there are plenty of specialist dating sites for over 50 and over 60 years old.

Here are a few of the best dating sites for men over 60. As I’ve established, good dating sites aren’t hard to come by, but if you aren’t tech savvy by 60 then it helps to have a head start.

UK Mature Dating  – – Great if you’re just starting out – simple dating for seniors. One of the better free dating sites over 50 year olds can use.

My Single – Your friends set you up a profile and find you suitable people. This is one of the most popular dating sites,

Fifty Already – is a paid site, but you can make sure you’re only lining up serious prospects


Over 50s – – One of the more standard over 50 dating sites, but with a great advice and tips section.


You always need to be thinking beyond the top dating sites, and if you find that the best dating website for you is a paid one, always have a backup on the go.


Spend as much time together as you can

At most other stages in life you need to ration your time to create interest. But if you plan to meet older women dating, you’ve also got a lot of ground together. and if you’re planning to retire soon, you’ve got to know you’re compatible and comfortable for long stretches.


Talk, a lot. Start doing new, interesting things together – explore old hobbies and fulfil old trips you wanted to do or films you never saw. You could have been using the best dating sites for men, and she could’ve been using the best dating sites for women, but if you can’t hang out for long stretches you’re wasting valuable time.


Don’t abandon your sexuality

You might be comfortable with your fading libido (men do adapt) but if you don’t make an effort sexually you won’t be able to support a relationship.


Go the extra mile, set up romantic dinners and walks and amp the chivalry up to a million. Don’t fall into a rut otherwise she will get bored and leave for someone the same age with a bit more spark.

I know it was a long one today guys, but there was a lot of ground to cover. I appreciate your staying with me and if you want more bespoke advice on getting success with women at any age the click here.