Dating 101 For Midlife Women

If you’re a single woman over 50, your dating priorities have changed a lot since you first started dating. Let us show you the five secrets you might not know about midlife men.

By Dave Singleton

or every woman in her twenties and thirties who’s looking for a ring and the man with whom she can settle down, there’s a boomer woman who’s been there, done that, and looks at men her age, asking, “now what?”

Dating changes when you and your dates are older. But it’s confusing when expectations change and you’re still playing by the old rules. Don’t you
Online dating is like learning a new language…
think it’s time to wise up to the new ones that might impact your dating hopes?

Yes, of course, boomers have baggage. Any well-lived life does. Hopefully, it’s the carry-on kind, rather than steamer trunks full of troublesome exes, meddlesome kids, and irksome habits from a couple of decades of increasingly getting stuck in your own ways.

Boomer baggage aside, how can you ascertain and match your dating priorities with those of men your age? Start by learning these five secrets aimed at helping you better understand the dating pool of single boomer men.

Secret # 1: Online Dating is Scary and New for Boomer Men, Too
Online dating is like learning a new language, and learning a language is harder at 50 than at 20.

“If you’re feeling a little unsure about dating online, keep in mind that the men in your demographic who are on the market, so to speak, may be feeling the same way,” says Kimberly Dawn Neumann, author of The Real Reasons Men Commit and founder of “The cyber world is new dating territory for many boomers, so instead of overwhelming potential matches with a laundry list of qualities you’re seeking, try to focus on what you think might be fun to do on a date or perhaps mention activities you’d like to explore with a companion. It’ll make you seem more accessible and less intimidating.”

Secret # 2: Single Boomer Men Might Be Clueless About How to Find You
Since the dating landscape has changed so much since your earlier dating years, boomer women need to get more active and put themselves out there. You can’t wait around for men to find you. Find them.

Every boomer woman who’s single and looking should get a letter like this: “Dear former Cinderella, stop waiting with one shoe in your hand. Prince Charming no longer makes house calls. At this stage of life, don’t wait for an invitation to the dance. Log onto your computer. Check out the prince’s online dating profile and ask him out. Do it soon. Love, Fairy Godmother.”

“If you want to be an Olympic swimmer, you have to jump in the pool,” says dating coach Evan Marc Katz, author of the new eBook, Why He Disappeared. “In an ever-changing world, there’s one thing you know for sure about online dating: these men are single and looking.” Don’t be afraid to contact them.

Secret #3: At This Stage, Boomers Have More to Lose (and Therefore, More to Be Cautious About)
Of the three levels that most relationships experience - lust, romance, and attachment - attachment is the hardest one for boomers. In many ways, meeting a boomer man is the easy part. The hard part is what happens next,
“Like you, boomer men have been through lots of ups and downs.”
and here’s why: When you’re younger and neither of you has acquired as much in terms of life baggage — friends, family, financial assets — it’s easier in some ways to merge lives. Now, your boomer date might be afraid of getting involved, merging households and finances, and managing the needs of any attached children.

“Your vital life structure is in play and you have something to defend and protect,” says relationship expert Dr. Philip Belove of “Home, life savings, and established social networks can all be an obstacle to attachment.”

Don’t let those common obstacles be the elephant in the room; address them. Get comfortable with discussing the very real and normal midlife entrenchments that will factor into any new romantic relationship.

Secret #4: Boomer Men Might Be Less Resilient
The truth is that age is no guarantee of maturity, acceptance, or resilience.

“Like you, boomer men have been through lots of ups and downs,” says Dr. Gilda Carle, author of Don’t Bet on the Prince ( “Unlike you, boomer men are not as resilient to life’s vicissitudes. Boomer men appreciate a woman who can make them feel better than they felt when the two of you met!”

Remember that perfect man you heard about when you were younger, the one who is equal parts successful, strong alpha warrior and sensitive, enlightened poet? He’s a myth. So if you were trained to wait for the perfect prince, reset your expectations. Smart boomer women know that there’s a big difference between a chipped diamond and a lost cause. You might be surprised at what you find if you exhibit compassion and understanding as you search for a slightly-used-but-still-wonderful prince.

Secret #5: Boomer Men and Women Might Have Different Goals
Have you considered the possibility that boomer men might not share your dating goals? For example, what if your boomer man wants to move faster than you do?

In traditional dating, sometimes it’s younger women who want to speed the dating train along. They have a biological clock to consider and might have fewer wild oats to sow than men. But this timetable inevitably shifts in midlife. Suddenly, the traditional track is a moot point. If you were going to have kids, you had them, and they’re somewhere between diapers and out of the house.

For boomer women discovering midlife singlehood, the solo life can feel liberating. Freed from the constraints of raising children, managing careers and taking care of everyone and everything, boomer women might find themselves freer to guide the form and velocity of a developing relationship.

For example, you might want a man for occasional companionship. Forget the traditional merging of lives. But your boomer man’s independence might be tempered by greater needs for connection and caretaking. It’s a mistake to assume you automatically know what a boomer man wants. Make sure you’re focused on goals — yours and his — before getting too involved.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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