Over 40 and Single? Happy Sassy Holidays!

Every year I write some version of ‘Over-40 and Single: How to Survive the Holidays, like How to Not Feel Like Crap this Year, or How to Avoid the Blues this December…

I encourage you to check out those posts because there is super practical advice on how to manage dating therefore the holiday season – which frankly, can be awkward and confusing.

But this year I was inspired by the younger generation to give you a different message:

Your dating and relationship status is no one’s business but yours.

This article in Refinery29 called Dear Single Women: This Holiday Season We Fight Back is a sassy and fun read.

It is geared towards single women in their 30s, but is wholly applicable to our generation of over-40 singles.

Part of what makes the holiday season especially stressful are all the questions you get from friends, colleagues and family about your love life. Comments and questions that are dressed up as loving concern but are frankly kinda rude and none of their business.

‘Still single?’Dating anyone?’What happened to so-and-so?’Sure youre not being too picky?’Have you tried Tinder, Match, getting a dog, wearing lipstick, losing weight…blah blah?

This year empower yourself to bat back some of those (too) enquiring minds with a message of your own, a la Shani Silver, the author of the article:

Please feel free to feed your family with its own ingredients. If our loved ones are so concerned with our single status such that they ask about it over turkey and yams, we’re going to call out the fact that they have done nothing to actually help us change it. If they want to walk onto this dance floor, let’s tango goddamnit.

‘Dad, I know you want me to be happy. I want to be happy, too. But bringing up the fact that I’m single at the holidays makes me very unhappy, because believe me Dad, I’m aware of the situation. So unless you’re hiding my husband in your back pocket, it’s really not your place to talk to me about a very personal area of my life that is actually none of your business. Also, if my husband is in your back pocket, take him out for fucks sake, I’m exhausted.

You are taking control of your experience and drawing the boundaries for what you are and are not willing to tolerate. And frankly, those questions are intrusive.

Of course, you may not want to lay it on this thick with your 85-year-old dad in a wheelchair – but it sounds like fun, right?

Instead you can reply with something like: ‘Yep I’m still single and looking. But, unless you know someone good for me, right now I’m focusing on just relaxing, being grateful and having a good time decorating the tree and enjoying this party. Another glass of champagne, Aunt Jo?

Or, if you are feeling really snarky, you can just wait a beat, smile slyly and say, ‘Wouldn’t you like to know?, wink.

Exit stage left.

This holiday take charge of those Nosey Nellies, and come up with a few ‘non-answers that will preserve your dignity, happiness and privacy. And give you a good giggle when you think about it later.

The holidays are to be enjoyed, not survived or tolerated. Especially if you are single and over-40. As Shani Silver says:

From the first cup of cocoa to the last bottle — I mean glass — of champagne I want you to enjoy every second. We’re not going to survive the holidays, we’re going to live them up. It is no longer our job to make other people feel better about our single status at this time of year. It is our job instead to change the way how to delete uberhorny single women are discussed, and to enjoy this time of year as much as anybody else.

Here’s to next year when your relatives meet Your One and do what mine did when they first met Larry: they asked me why I was so lucky to meet such a great guy. (Really, that happened.)

Happy Holidays, girlfriend!

Dirty John was a podcast and is now a mini-series on Bravo about a middle-aged woman who meets a man online and enters into a whirlwind courtship. It ends horribly, practically destroying her entire family.

Dirty John is a cautionary tale, to say the least. What can a single woman over-40 selecting love using online dating learn from this true story besides having the crap scared out of her?

Lots. Read on.

(But wait, before you do, I want to be clear: this is not a blame-the-victim story. This is certainly me doing my job: leading you to your grownup love story in a safe and drama-free way. And hey, I set myself up for lots of Dirty Johns over my 30 years of singledom. It was sheer luck that I only fell for creeps, not psychos.)

To continue…

Episode 1 shows Debra, a successful, attractive woman over-50, going on first date after first date with men she’s met online.

During the montage, Debra is depicted as being grossed out by her date’s manners or drinking habits, turned off by their over-sharing, or mostly just bored to tears.

( Any of this sound familiar?)

Then…ta da! Debra meets Dirty John.

John is charming, funny, sexy, good-looking, and so clearly into her. They have scintillating conversation, lots of laughs, and boatloads of chemistry. They are off to the races from date one.

We know this story does NOT have a happy ending. So, why does such a successful, smart, otherwise-confident woman with four marriages under her belt keep seeing this guy?

It’s because Debra is what I call A wow-me woman.

Introducing the Wow-Me Woman.

The Wow-Me Woman is stuck in her teenage girl’s fantasy. Her surface feelings and intuition guide her. She firmly believes that one day her prince will come, they will lock eyes, and BANG…it will happen! She will just know.

Her prince will sweep her off her feet. He will be charismatic and charming and, upon first meeting, they will laugh, laugh, laugh! They will have all the same things in common. Their conversation will flow and be thrilling, with none of that pesky silence.

Here is how dating most often goes for the Wow-Me Woman:

She dates and dates but never meets men she likes. Once in a very long while, she meets someone and feels The Buzz. (You know, that chemistry thing? Bzzzzzz!)

At last, her prince appears.

Their first date is incredible.

He could be The One!

He instantly starts texting and emailing, and she jumps right in. They talk and/or see each other every day. He tells her how special she is. He’s never met anyone like her. He impresses her with flowery compliments, spectacular restaurants and musings of what they will do together in the future.

She’s more and more convinced that her initial feeling was right on: he’s amaaaaazing!

There is a huge difference between a good date and a good mate.

When I’m coaching her, she tells me: ‘It was incredible! I could tell right away that we had an amazing connection! I’ve been waiting so long to meet this man! (I’m always tempted to reply, ‘How’s that instant connection thing working for you so far?)

And then…

the story changes. Most often he disappears. But sometimes, like Dirty John, he sticks around alternately wowing her and showing signs he has very different – or very bad –intentions.

Now…listen (read) closely here:

The Wow-Me Woman, once wowed, ignores any contrary evidence that they weren’t meant to be.

Debra loved John…

even though her daughter had a horrible vibe about him from the beginning…

even though he stomped out of her house when she tried to hold her boundaries during their early make out session…

even though she was never quite comfortable with how he made his money…

even though, even though, even though.

Nothing could convince her once she saw his charming side and decided he was The One she’s been waiting for all these years.

She’s kissed a lot of frogs and she’s not about to give up her prince!

If you continue to watch Dirty John you will see the horrible consequences of Debra ignoring an endless stream of even-thoughs. From the beginning, she threw away any rules, boundaries or healthy skepticism she likely applied to all those other (non-shiny) guys.

The fantasy ends.

Look, we were all sold a bill of goods with the knight in white armor, happily ever after fairy tale crap. But as grownup women, let’s all agree to give up that fantasy. That’s the only way we can find lasting love with a real-life, warts-and-all, loving, high-integrity man.

…feeling safe, understood and valued…these are the yardsticks by which you can measure a man’s potential in a meaningful way.

Debra is a victim here. He was a nasty, criminal, pathological dude. But Debra let her desire to live out her Prince Charming fantasy blind her to the red flags he showed her from the beginning. (And once again, I get it. No stones being thrown by me here.)

If she had well-thought-out rules and boundaries that guided her decisions…

if she had clear must-haves…

if she weren’t so dead-set on being wowed on the very first date…

if she was willing to look deeper at the other men she had discarded…

it’s likely that she would have run from Dirty John or never dated him in the first place. This story would have had a very different ending.

There’s a difference between a good date and a good mate.

Yah, the Dirty Johns of the world make for great dates. But there is a gigantic difference between a good date and a good mate.

A good date is momentary. Our grownup woman, if she’s trying to find love, needs to examine whether a man has what it takes to make a great mate.

I was single for about 30 years before I became a first-time bride at 47. I know quite well that when we drive our love life by fantasy and feelings alone it leads to all kinds of tumult and bad decisions.

What I finally learned, and what I teach the mature women I coach, is that in order to be truly fulfilled in a relationship we have to be able to articulate the grownup feelings we need in order to be happy for a lifetime.

Charming and funny feels exciting. Having a man seem totally into you is incredibly powerful, especially when he comes in a shiny package. But feeling safe, understood and valued…these are the yardsticks by which you can measure a man’s potential in a meaningful way. After 12 years of marriage and watching countless women find loving, devoted partners…this is the real juicy stuff. The stuff that lasts a lifetime.

The mature dater sets clear boundaries to keep herself safe. She is clear on what she needs in a life partner. She knows exactly how she wants to feel when she’s with him AND when she’s not. (That ‘not time is usually when the truth comes out. Pay attention to that!)

The mature dater knows it takes lot more than excitement and Shazam to keep her happy. And safe.

The mature dater balances her head and her heart when making decisions about who to let into her life, into her bed and into her heart.

If you find yourself getting swept away and can’t articulate why (except to say something like ‘He’s just so…awesome!), then tap on the brakes my friend. If this is truly a good man he will still be there when the grownup part of you decides he ‘s got what it takes for you to be happy as partners.

As Lori Gotlieb says in her book Mr. Good Enough: The Case for choosing a Real Man over holding out for Mr. Perfect: finding a guy to get real with is the real love story.

Life and love with a maybe-not-so flashy solid grownup man could make you so much happier than chasing after some elusive fantasy. (And catching one may be worse!)

So, if you’re a single mature woman dating and looking for love, I hope this helps you understand why smart women can make really dumb choices.

If Debra had dumped her need to be wowed, paid attention to her even-thoughs and judged Dirty John based on the grownup stuff, she would have avoided him and all the damage that ensued.

I have three principles that help women date like a grownup:

  1. Balance your head and heart.
  2. Show kindness to yourself additionally the men you meet.
  3. Take responsibility for your actions and outcomes.

Debra scored miserably on principle #1 and #2 (she was kind to him but certainly not to herself). But she scored on #3. Debra ultimately took responsibility which included bravely sharing her story. By doing so I have no doubt that she has helped other women Just. Say. No. to going after the fantasy and finding the Dirty Johns out there.

PS: My Over 40 Love School is a 9-month program for mature women who want to find real love, are tired of the same old silly advice as they are ready to get to exert effort and get love done!