Question (which has been slightly edited to preserve the anonymity of those involved):

Anonymous 20-something female writes:

Hi Stacie,

A friend of mine recently embarked upon your blog and I have since caught up on your past blogs. Great website!

I am writing you because I was curious to hear your opinion concerning significant age differences for dating/sexual encounters. To be more specific, this involves two individuals whereby the man is over twenty years older than the woman (she is in her 20s), not to mention he has children (not much younger than her)!   My friend who discovered your blog is seeing this man and I am so concerned for her well-being.  I know little about this man and his intentions, but it worries me that there is such a significant age difference, not to mention a generational difference.  They are at such different stages of their lives – him as a father, while she is beginning her career.  I know it is her place to make a personal decision but she rarely speaks about her feelings given she knows the situation itself is highly controversial and seemingly unacceptable.

I was wondering if you would consider blogging about this controversial topic.  I would appreciate your wisdom and advice on this matter!

Look forward to hearing from you! 


I can understand why you’re concerned, that is definitely a significant age difference which is amplified by the fact that their priorities are so (presumably) different right now – as you mentioned – her beginning a career, him as a father with parenting responsibilities.

Without knowing your friend (including her patterns of behaviour, her dating history and her vulnerabilities) it’s difficult for me to offer an opinion on whether this particular relationship is an unhealthy one or whether there’s cause for further concern.  Even if I did share your concern for your friend, this is likely something that needs to play out.  If you feel that her physical safety is in jeopardy or that there is any kind of abuse present then I recommend that you call me to discuss further.

For most of my adult life I have gravitated toward older men.  When I was 21 years old I dated a man who was 33 years old (and my family and friends will challenge that he was that young…apparently he looked like an “old man”, although I didn’t see it because I was so intrigued by him).  Friends, family and colleagues all had variations of the same skepticism: “An older man only wants one thing with a girl your age”.  That unsolicited consensus turned out to be accurate.  Well…only partially.  He did want only one thing – but it wasn’t sex (although he wanted that too) – it was marriage.  He was looking for a wife.  We dated for 18 months before deciding that marital bliss was not ours to be shared.

I tell this story this for two reasons:

1)      I had a curiosity, at an early age, about older men and I know that I’m not alone.  Almost 16 years, and many relationships later, I do not regret the experience despite a painful break-up and some lingering consequences.  I also now understand where my tendency toward older men came from and it’s given me tremendous insight into myself as I engage in new relationships.  Your friend may have the same tendency and if that’s the case she needs to have the freedom to explore it.  It could be a rite of passage for her, per se, and I’m hopeful that she too will look back – with the benefit of hindsight – with few regrets and many lessons learned.

2)      Not all (older) men are created equal.  My ex-boyfriend was not the sex-addicted, may-as-well-be-a-pedophile perv everyone assumed him to be.  While it seems odd that this father has an interest in your much younger friend, his intentions could be honourable.  By your own admission, you don’t know what his intentions are and perhaps benefit of the doubt is appropriate right now.

I don’t know that the nature of your friend’s relationship could be considered controversial in this day and age, despite how uncomfortable it may make you (or others) feel.  Look at Michael Douglas and Catherine Zeta-Jones, who have 25 years between them, or Scarlett Johansson and Sean Penn.  She’s 26 and he’s 50…with children and at least two ex-wives.  I know what you’re thinking.  “But they’re celebrities…it’s different!!!”  While that may be somewhat true, it’s also a fact that you see these same unconventional relationships in “real life”.  Just as with Hollywood couples, sometimes they work, and sometimes they don’t.

When we look at the issue of age in isolation (or any one variable, by itself) we cannot possibly be seeing the full picture.  Personally, I’ve dated men 16 years older than me and more than ten years younger than me.  I came out of all of them relatively unscathed and in most cases age had little to do with the break-up.  My unhealthiest and most toxic relationship had nothing to do with an age difference and my two *favourite* post-divorce relationships were with one man who is 13 years older than me and one man who is ten years younger than me (and I don’t mean you SW).  Relationships work best when the people involved are aligned to the same goals, priorities and values.  That can happen among people of varying religious and cultural backgrounds, age groups, socio-economic status and political affiliations.

I’m less concerned with the age difference between your friend and this man and more concerned that she (and you) believes that she’s engaging in unacceptable and controversial behaviour.  If there are genuine feelings involved between her and this man, she should be able to enjoy and explore them sans guilt or shame.  Attraction is a fascinating topic…one I could blog about all day, and explore endlessly.  What attracts two people to each other is often mysterious and indescribable.  You may not understand what’s drawing her to this man (and she may not either) but the fact remains that there is something bringing them together.

I can tell from your e-mail that you are a loyal and caring person who wants what’s best for your friend.  Given that she is now involved in an unconventional relationship, subject to much scrutiny and judgment, why not be her safe place to fall?  Is it possible for you to put your apprehensions aside and be there to encourage and support her?  Your friend is on a journey right now and she’s going to follow this path she’s on…with or without you.  She may stumble along the way, she could take a few wrong turns and she may even get lost.  If she falls down, she may need some help getting up.  If she knew that there was someone there, to listen without judgment, she may be more inclined to share the experience.  My guess is that she speaks so little about it right now because she knows how people feel about her choice and she doesn’t want to hear the criticisms. 

The situation is complicated enough – his kids, their age difference, her shame – it would be great if you could be the one person  where she feels that conversation (especially about him) is easy, where things are simple.  She likely needs that.  What is the worst thing that could happen as a consequence of her continuing to explore this relationship?  She might get hurt?  She may end up disappointed?  She may even get taken advantage of?  Sure.  All possibilities, however, remember that those worst-case scenarios could be equally looming in a relationship with a childless, never-been-married man her own age.  What’s important is who she is – in this relationship, or in any relationship – how she carries herself, how she manages conflict, how she sets and maintains boundaries, how she feels about, and protects, her sense of self. 

I am confident that this is one of many experiences to come, for her…this will likely not be her last.  As her friend, I feel that it’s your “job” to support her by maintaining or building up her self-esteem so that she doesn’t lose herself in this relationship and to encourage her to put her best foot forward…neither of which should have much to do with who he is.

I hope this answers your question and gives you the perspective and insight you were looking for.

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