Boomerangst: Turning Dilemmas Into Discoveries – Dating An Older Woman

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Why is it acceptable for an older man to be with a younger woman but not the reverse?


Q. I am a 40-something man who cares very much for a woman 14 years my senior. I won’t say we’re in a relationship or even dating, but I need your help to overcome the barriers. Even though I’ve known her for seven years, only recently were we able to even talk about how we felt or what we thought. I don’t make it a habit of seeking older women but I’ve fallen for her. She thinks it’s inappropriate. I think that, while it is uncommon, such relationships exist. I equate being against them to being against the mini skirt or gay rights – merely ideas society was slow to accept. I’m also the victim of a double standard. Why is it more acceptable for an older man to be with a younger woman but not the reverse? Coincidentally, her previous husband was 20-plus years her senior, so I’m very confused about her apprehension. Your advice?

—Jack, Mississauga, Ont.


A. It is a double standard. You’re right. But does it really matter? According to a study by the Australian Bureau of Statistics, the proportion of relationships where women were at least 10 years older than their partner rose 23 per cent between 1996 and 2006. But sometimes attitudes are hard-pressed to catch up to reality, as you point out – be they public or private.

“We have strong ‘shoulds’ on ways of partnering up,” Dr. Kathryn Elliott, assistant professor of psychology at the University of Louisiana, told NBC news. “We are victims of inner-critic constrictedness. We think we should only weigh 120. We should marry people within two years of our age. We pathologize anything that isn’t within those shoulds.”

So where do you go from here? Find out why this friend of yours thinks a more intimate relationship is “inappropriate.” You need to understand what her concerns are. Maybe it has something to do with the age difference of her former husband. You just don’t know.

The bottom line is you need to get answers – in a gentle, non-confrontational way, according to Dr. Kristen Mark, a sex and relationship researcher and professor at the University of Kentucky (who got two of her three degrees in Canada).

“The word ‘inappropriate’ is so vague,” she says. “The best way to approach this is to be completely honest and say something like, ‘As you know, I want to be more than friends and I really want to talk about what the barriers are to moving forward. Regardless of the outcome, I need to know what your thoughts are’.”

And a final word about a younger man-older woman relationship from self-described Love Coach, Sydney-based Carolin Dahlman: “Success has nothing to do with age. It’s about how you create your relationship. If it’s built on love, respect and communication, you’re on to a winning formula, no matter how old you are. If you’re in love and happy, who cares? Don’t let society tell you it won’t work. Brave people follow their heart. Others follow other people’s opinions.”


Send Diane a brief description of your dilemma, along with your first name and where you live, to [email protected]

A professional journalist for more than 25 years, Diane Sewell has written for some of the top newspapers and magazines in Canada and is a baby boomer herself. Her new blog “Boomerangst: Turning Dilemmas into Discoveries” is interactive with readers and focuses on life issues – like aging, dating, second marriages, sex, death, family and fashion. Diane will use her expertise to find the right expert to help solve your predicament, unearthing kernels of truth and quickly getting to the heart of the issue.