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Dating 101 for midlife women

Dating 101 for midlife women

By Dave Singleton

For 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 the 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 think it’s time to wise up to the new ones that might impact your dating hopes and dreams? Yes, of course, boomers have baggage. Any well-lived life does. Hopefully, though, it’s the carry-on kind rather than steamer trunks full of troublesome exes, meddlesome kids and irksome habits from a couple of decades spent increasingly getting stuck in your own ways.

Boomer baggage aside, how can you ascertain and match your dating priorities with those of the single 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 DatingDivaDaily.com. “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.”
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Secret #2: Single boomer men might be clueless about how to find you
As the dating landscape has changed significantly 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. In fact, 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 Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad. “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 cycle through — 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, 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 your lives together. Nowadays, though, your midlife date might be afraid of getting involved with someone new, merging two households and their 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 psychologist and relationship expert Dr. Philip Belove, author of Rabbis in Love. “Home, life savings, and established social networks can all be obstacles to [forming] an attachment.” Don’t let those common issues be the elephant in the room; address them instead. Get comfortable with discussing the very real and normal midlife entrenchments that naturally factor into building any new romantic relationship with another person.

Secret #4: Boomer men might be less resilient than you think
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 (www.DrGilda.com). “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 dating goals
Have you considered the possibility that boomer men might not share your goals when it comes to dating? For example, what if your boomer man wants to move things much 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 moving out of the house.

For women who are discovering singlehood for the first time in midlife, living solo 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 romantic relationship.

For example, you might want a man around just for occasional companionship. Forget about the traditional merging of lives society expected of you in your youth. But your boomer man’s independence might be tempered by his greater needs for forming a connection with someone and caretaking. It’s a mistake to assume you automatically know what a boomer man wants. Make sure you’re focused instead on identifying any love-life goals — both yours and his — before getting too involved.

Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Visit his website, follow him on Twitter, or email him.