Dating While Over Forty

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Sure it’s scary, but the rewards are worth the stress


In my mid-20s – in the early days of what I thought would be my life partnership, just after we bought a house and I became pregnant – I was part of a team tasked with developing a safer sex pamphlet for women 40 and up. Full of smug young love and excitement about my new life stages, it was hard for me to imagine what it would be like to be dating in my 40s.

And whaddaya know? Here I am, a single woman in her 40s. Although I often get asked about my relationship status, I am rarely, if ever, asked about my dating process. We ask younger people if they are dating or seeing anyone, but I am usually asked if I am in a partnership or not, end of conversation. Granted, that is absolutely what I want, but it’s not as if you can go from singledom to partnership without the necessary and fascinating world of dating. We are stuck with a picture of dating as something teens or university students engage in. There doesn’t seem to be permission for us over 40s to fully embrace, participate in and reimagine dating for ourselves.

Well, my midlife and beyond friends, we may not have a roadmap, but we can still start the journey. I’m not going to pretend dating or finding love and companionship will always be easy, but here are some tips to getting going.

Know what you want

Are you looking for a steamy hookup, a companion for events or a longterm partnership? These, and many others, are legitimate reasons and outcomes of dating, but it’s important to know what you want. You don’t necessarily need to put it all out there in your profile or on the first date, but knowing what you want will ultimately help you to find the right match.

Go online

Our generation has hangups about online dating that the younger crowd just don’t seem to have. Online dating may feel too foreign, desperate, exposing or overwhelming to folks in our stage of life. Online dating is certainly not the only show in town or a panacea for all dating woes, but its a great resource, especially in our time-starved lives. No matter what kind of dating you are looking for – casual or commitment-focused – online dating can be of service. If you would like help crafting a sexy and authentic profile, please contact me!

It’s scary

Dating and remaining in our comfort zones rarely coexist. Dating, even if you are fully comfortable with the idea, asks us to expand ourselves and be vulnerable.  One thing I am definitely noticing about midlife is my decreasing energy levels and increasing comfort with myself in my own space. I don’t feel the same restlessness I did in my younger days, which is both a relief and a drag. I need to remind myself that doing scary things – not necessarily bungee jumping or skydiving kind of scary – is still an essential part of living a curious and engaged life.  Lots of folks have told me (and themselves) they don’t want to bother with dating. They don’t need it or are happy on their own. While I certainly believe we can be satisfied with single life, sometimes these proclamations are really a way to cover up the fear of getting out there.

It’s fun

Yes, dating is scary, but it also has its rewards. Even if you don’t immediately get the relationship or partner you want, it’s fun to meet new people, go on dates and have romantic energy in life. If you haven’t been on the dating scene for a while, you may have forgotten how energizing it can be, how much you can learn about yourself, others and the world, and how important it is to walk into the great mystery!

It’s a number games

This has not been my best dating year. I oscillated between the Sahara desert and a series of bleh dates. What started to creep in was the mantra I use to protect myself from dating disappointments: “I should just give up. It’s never going to work out. Why bother?” Although it’s understandable to start feeling defeat, dry spells and bad dates don’t mean it’s never going to happen or it’s time to give up. Of course, when it’s time take a break or a rest, I need to honour that, but I also remind myself to keep at it, try to enjoy the process and remember that since there are more single people in Canada than coupled, there are lots of eligible possibilities out there.

There are no rules

If you Google “Dating Rules,” you will get about 76,800,000 results. Clearly, I have an unpopular opinion, but I believe there are no global or even permanent personal rules regarding dating. Throughout my dating life, I have tried to make some clear rules like if it starts off too quickly, it won’t work out. If it’s too slow, it won’t work out. If his name has only one syllable, it won’t work out (that’s how desperate I got for a feeling of control). If he has kids, it will work out. If he has kids, it won’t work out. While dating provides an excellent opportunity to learn more about your own personal values, that’s not the same thing as rules. Rules are an attempt to control, and dating is all about opening yourself up to possibility. We need full permission to trust ourselves as we go along, try things out and embrace the process.

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I’d love to hear from you. Contact me at with comments, questions, or if you’d like to find out how working with me can help you get back out there.

Adina head shot

Adina Lakser is a Winnipeg-based sex coach, writer and mother. Visit her at or her Aquarian column Pillow Talk


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