A Baby Boomer’s Dating Advice to a Generation X-er

One thing we baby boomers have that younger generations don’t is experience … so it’s nice when they ask us for advice. That’s what happened to boomer Erin O’Brien of Redondo Beach, California, when a Gen-X friend was having problems with her dating life. In the afterglow of Valentines Day, Erin has shared her advice with us; she calls it, “Last Man Standing: A Baby Boomer’s Dating Advice to a Generation X-er.”

A friend of mine has found herself recently relocated, and recently single.

Erin O'Brien

Erin O’Brien

Although I haven’t been in the dating pool for years, I was flattered when my friend solicited my advice. After culling her list of prospects on a dating website, she had narrowed down her choices to three bachelors — whom I’ll call Tom, Dick, and Harry.

But before I could be of service, I needed some information on the eligible young men, based on the first dates.

There were important questions to ask regarding each suitor: were there any awkward pauses? If so, what was their duration? Did he maintain eye contact (or did he glance at his iPhone, or your cleavage)? Did he reach for the check in a timely manner? Since my friend didn’t plan on marrying, their surnames were a moot point, but I said first names would be helpful.

dating_onlineI asked how she would describe each bachelor’s style:

a) preppy, with a hint of savoir faire
b) earthy, granola, and introspective
c) disarming, yet self-aware
d) other (please state)

As it turns out, Tom was a doctor:

Lizzie was slightly neurotic,
Afraid of dating psychotics.
She hesitated,
Surprise awaited:
Tom prescribed antibiotics.

dating_40sRichard (Dick) was a little too familiar:

Dear Richard you cause me to cringe,
In fact come completely unhinged.
So please do not touch,
Don’t like you that much;
My dating experience tinged.

My friend liked the limerick, but requested a sonnet and so I obliged:

Ode to Richard

Jane Austen

Jane Austen

I first saw your face and sighed to myself
Pondered reasons why you traversed the coast
As I gazed at my Jane Austen bookshelf

On Date.com you ranked better than most
Contacting you seemed like a no-brainer
I saw you owned a suit and matching tie

You with looks of a personal trainer
And also seemed like a regular guy
However my hopes were completely dashed
When you dared touch me without my consent

In the days that our awkward date has passed
I find my tolerance totally spent
Contemplating a life of solitude
Until I can improve my attitude

… and I even threw in a haiku:

A crass gesture is
felt on and beneath the skin
causes me to cringe.

park_rangerThe front-runner, Harry, rated two limericks:

There once was an L.L. Bean guy
Who, in khaki, caught Lizzie’s eye.
No polyester,
For that would test her,
Although at work he wears a tie

There once was a tall park ranger
Who met a beautiful stranger.
He took out his Visa
To promise her pizza
And to keep her out of danger.

My friend mulled over her previous dating experiences, which I reminded her in retrospect were a bit disappointing:

There once was a man from Bolgar
Whose table manners were vulgar.
He spoke as he ate ,
His fork was a rake
And he slurped his cup of Folger’s.

In conclusion,

Lizzie hopes Jane Austen’s Emma
Can solve her dating dilemma.
Fate will intervene;
It’s yet to be seen
Who’s received on her antennae!

Enjoy Other Stories on BoomerCafé ...


  1. Hey! Great post. We have a friend who keeps getting burned by choosing losers and scammers, especially the latter, on dating sites. You should write an article on how you avoid those sometimes serious and expensive problems. Our friend is a widow and obviously vulnerable as a result. Your advice could be very useful for people with their problem which often repeats itself.

Post a Comment

Your email address will not be published. Required fields are marked *