5 pieces of expert advice on dating after 50

dating later in life

This week, I had the honour of moderating a panel discussion on the topic of dating in midlife and beyond with long-time dating columnist and author of The Later Dater Valerie Gibson, and matchmaker and online dating expert Julie Ritchie of Six Degrees Introductions and AMillionMatches.com.  

Held after a staging of Surrender Dorothy, Liz Best’s new play about online dating after 50, it was an evening of laughter, candid confessions, and whole lot of insight.

If you are dating around or past the half-century mark, here’s the Coles Notes version of what went down.   

1. Your love life doesn’t have to end with your last relationship

Although for the first time in history it’s not taboo for women to date later in life, some older singles still feel that ship might have passed. And that’s a shame, says Gibson, because many of us will live to be 90 or 100, and that’s a long time to be lonely.

The consensus of the panel was midlife is an incredible opportunity to rediscover yourself and finally live life by your own rules, and that includes finding love.

Although technology, expectations, and norms about things such as who makes the first move and who pays have changed, as the success story of one audience member proved, it is entirely possible to meet a good man or woman online. Just be aware that dating later in life can differ significantly from dating in your 20s.  

2. Put your best face forward and keep your profile concise

Online dating is a proven way to meet a wider variety of people. And, in the era of scrolling, swiping, and seemingly unlimited choice, your online profile pictures are what gets his or her attention.

“Men fall in love with their eyes, women fall in love with their ears,” says Ritchie. “You really need great photos to be successful online.”  Get high quality shots that show you at your most attractive (out-of-focus bathroom selfies simply don’t cut it). 

And what about profiles? “Keep it brief,” says Ritchie. The idea is to give them a sense of who you are without giving away too much of the mystery. You can dazzle them with your sparkling personality in person.

Also, don’t be afraid to reach out to potential matches if you are a woman. The days of men having to make the first move are long gone.

3. Be aware of red flags

If he seems too good to be true, he might be. There are con artists who prey on older women by developing online “relationships” with them, warns Gibson. If they ask for money run.

But there are other less criminal types you need to be aware of: for example, men who want someone to look after them either financially or in poor health while they age. “They are looking for a purse or a nurse,” says Ritchie.

Also, beware of people who don’t want to meet in person, can never make solid plans, or have sparse information on their profiles.  

And keep in mind it’s not online dating – it’s online meeting. You never really know a person until you connect with them in real life.

4. Drop the superficial bucket list

“Online dating can make it seem like there is a lot of choice out there,” said audience member Anya Romanova of The Modern Love Project, a company that holds house parties where progressive singles can meet. “And it makes people think there is always someone better.”

It’s an easy trap to fall into, especially if your criteria for who you date centers around things like looks and income. Too many woman focus on things like wealth, status and looks, says Gibson, rather than character and the internal qualities that can make a good relationship.

“When you only focus on these things, you pass up a lot of really great men,” agrees Ritchie.

5. Let go of expectations

Above all, all of the panelists encouraged single women and men in their 40s, 50s and beyond to stop expecting fireworks on first dates, let go of their type, and date outside of their comfort zone.

Try someone new, with no expectations other than to meet someone new. If they are decent and you had a good time, see them again. When you do, you’ll be surprised what can happen. (It worked for me!)





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