Category Archives: Flirting After Fifty

You’re either “wooing” or you’re not.

Gentlemen – forget what women say about independence and equality and paying their own way; when it comes to dating, you’re either wooing or not. It’s understandable that you don’t want to be taken for a chump, but you can reduce your exposure AND still impress the ladies, by following a few simple strategies:

Invite her for Sunday brunch. It’s low-key, you get to see her in the light of day, and the competition is not as intense for her attention. Show up wearing something nice, clean and as though this encounter is important. Don’t show up in sweats, unshaven, with a baseball cap and your Sunday casual on. An opportunity to impress is just that – an opportunity. You don’t want her thinking you didn’t care enough to clean up a bit, even if it’s a Sunday. Also, the meal is less costly than dinner, and you can control the amount of liquor consumed by ordering a Bloody Mary or Mimosa, versus a bottle of wine. And yes, you pay, even if she offers. You can note that her offer is nice, but you have to be “nicer” and refuse. Dating is an investment of your time, and if you’re not willing to spring for breakfast, it will make her wonder about whether she wants to invest her time in you.

It’s not about you. When you are face to face, don’t fill her head with all the things that are wrong with you, or let her fill yours with the same. Focus the conversation on good things – things that make you happy, things that interest her, things that make you laugh. A date isn’t the time to process lost loves, jobs, career stalls, politics or health problems. It’s an opportunity to show what lights up each of your lives; the more she talks, the smarter she thinks you are.

Make eye contact. Nothing spells disaster faster than a roving eye – either for others in the room or for her body parts. Show you are interested in what she has to say by remaining engaged in the conversation, as though she is the only one in the room. It’s very flattering, and nothing says “I’m interested” more than keeping the conversation and your eyes, on her.

Don’t rush the intimacy. Don’t think that jut because the meal went well that she’s dessert. If you have a chance to touch, keep it informal (upper arm, maybe the hand, a gentle cheek kiss) for starters. No jumping her in the parking lot, hand around the waist in a “you now belong to me” hold, or god-forbid, French kissing. Keep it light and take your cues from her. If she feels pressured, you have just wasted your time because she won’t want more of it.

Follow-up. Right away, if you’re interested. By Monday, if she hasn’t heard from you, she will start to rattle off all the reasons why you aren’t for her, as a way of dealing with rejection. At the least, call her right away and let her know you had a good time – if you did, and that you are interested in getting to know her – if you are. Feel her out as to whether she’d like to get together again. If she says yes, offer a time and activity – perhaps something also low-key, like a visit to a gallery or a walk to see the Cherry Blossoms. Maybe she’ll suggest a home-cooked dinner or a movie. Take your lead from her. If she puts up some obstacles, suggest that when she’s free you’d like to see her again, and ask that she let you know. Put it in her lap. At least you will have done the right thing, set the stage for another “opportunity” and vetted her interest – all for the price of breakfast.

About Cougars

I’ve been asked a lot, “What about Cougar women?” The question is often asked as though it’s a really great thing that women are going for younger men, and getting them. And I suppose for some women, that’s great. For a while. If the idea is to flirt and attract, one could do that with any age. It’s when the flirtation has the potential to migrate into something more that I offer a bit of caution.

I had an aunt once say to me, “Better to be an old man’s honey than a young man’s slave.” When I first heard that, in my thirties, I thought it was a creepy idea. But now that I’m beyond my fifties, it makes a lot of sense.

I’ve observed women who are with younger men – often much younger – and there is always the feeling that their connection to younger men is tenuous, and easily broken once they turn the corner and start looking their age. This can be a frightening time, and can add to a woman’s sense of insecurity, causing her to dwell on every wrinkle, every gray hair, every piece of evidence that she is the older woman in his life.

If a woman can live with the evident and inevitable differences between her and her lover, or her younger competition, there is nothing wrong with a younger man in her life. But when it becomes a source of pain and sorrow, and the age gap widens with every passing day, I say it’s not worth it.

Maybe my aunt was right. Besides, at this age, older men don’t look that much older, and the gap has definitely closed. A woman needs to keep her expectations of the future realistic, and part of that is realizing she has a past. Having someone in her life who shares that history may make it that much easier to deal with the present – as is it – and not as she wishes to pretend it to be.

Beware of Social Saboteurs

I was asked recently on a radio interview what some people do to sabotage their chances for finding romance. I had to talk fast because there were a lot of things I wanted to say but here are just a few:

One of the biggest mistakes women make is to stay home, afraid that going out alone is too risky, too embarrassing, or too lonely. And they wonder why they don’t meet anyone. Get out of the house, and get out of your shell. Go places – the theatre, a wine tasting, a cooking class, a reunion – any place where you can talk to people. It doesn’t matter if everyone else is “coupled up”; you never know what their circumstances are (or aren’t). And besides, it’s just conversation.

Another thing people do is to disclose too much too soon. Dumping one’s old baggage into the middle of the conversation to muck around in isn’t fun for anyone. Maybe they’ll think your baggage is just too heavy to carry.

Social saboteurs crop up all too frequently but they can be avoided with a little insight.

Here are a few:

  • If you’re talking to someone, be present and make eye contact. Don’t let your eyes roam the room for someone better to speak with.
  • If you’re interested in getting to know someone, give them a chance to tell you who they are. Don’t fill the conversation with information about yourself. Draw them out.
  • If you want someone to get to know you better, make it easy. Don’t put up obstacles to conversation or make it a challenge to get you to open up. You don’t have to reveal deep dark secrets, but you can share the highlights with enthusiasm.

Remember, don’t try to make the overture the entire symphony. It’s just flirting – a conversation starter – and to burden the moment with too much pressure will certainly bring it to a quick end. Better to keep it light, and keep it fun.


The Goal of the First Date is to Get to the Second Date

Why oh why would you want to share all your stories, your health conditions and your baggage with someone new right off the bat? The problem with disclosing too much too soon is that you give too many reasons for wanting to bail out! We all know that sometimes we grow to like and love people we might have avoided if we hadn’t had the chance to see that there was so much more to that person. But sometimes, as we get older, we think that we are running out of time, so we may as well get it all out on the table. Stop! Don’t think that way! What we don’t have time for is to waste or squander our opportunities to find love by throwing so many obstacles in the path that our romantic interest runs away rather than runs the gauntlet we’ve set before him.

The goal of flirting is to establish some interest. SOME. And to get a conversation going that continues to draw him in with greater interest. “Tell me more. I’d like to learn more. I want to get to know you.” It doesn’t mean all at once.

Parse out the information a little at a time, and that doesn’t mean the negative stuff either. Leave something for the next encounter, and the next, and make your life, and his, like a good novel where each time you meet, you cover a new chapter. Don’t try to rush to the back of the book to see how it ends. Take it slow, and let it unfold.

After the first date, get the second. And after the second, aim for the third. As you log in the moments, you are building up to something more, one step at a time.

“Nothing Helps a Bad Product Fail Faster Than Good Advertising”

I’m often asked what I think about fudging the truth on photos and personal descriptions using online dating services. Being in marketing for so many years, I learned that there are various stages to developing a relationship with a customer, and some of these lessons can apply to flirting and dating as well.

  1. Have a good product that meets a market need.
  2. Identify those characteristics that best suit the market and present them honestly to those who are most likely to be interested.
  3. Put the product in the place of most potential.
  4. Stand behind the product.

What does this have to do with relationships? Well, before you go looking for love, it’s a good idea to assess your “product.” Are you well groomed? Do you have interests? Are you ready to go to market? If not, don’t try to package yourself with whitewash.

What’s the point of trying to sell yourself using a photo or description that doesn’t reflect who you are today? Assuming you do get to the face to face for coffee, your encounter is sure to disappoint as “not as advertised” and there you’ll sit, feeling foolish and rejected. Why subject yourself to that humiliation?

But assuming you are honest with your assets, and want to meet someone who might just be interested, it’s essential to do some advance work and determine where such a person might be found. Putting yourself in the place of most potential means you have to think through the likely places you’ll meet someone who’s looking for someone like you.

And finally, when you do get to meet someone interesting, be yourself, but be your best self. He doesn’t need to know your life history or medical conditions. He doesn’t have to be pulled in to your family drama or career insecurities, at least not at first. Allow some time to get to know each other, a little at a time, until he wants to know more.

Too Good or Not Good Enough?

Like many women, when we get together someone is talking about men. Either their too good to be true, or not good enough. Or plentiful enough. Or tall enough… the list goes on. Why are women so fond of belittling themselves, in the belief that “never the twain shall meet?”

My guess is that it’s due to either an over-inflated sense of expectation “Someday my prince will come” or an under-developed sense of self “All the good ones want younger women.”

I see so many great women, and men, who have found a realistic way to “couple up,” without blinders. In fact, they see each other exactly for who they are, and like what they see. A realistic woman isn’t deluded by fantasies royalty, but her prince charming is usually a regular guy who just happens to be a prince of a fellow to her. And treats her like a queen.

In looking for love, it’s important to remember that a woman who makes a man feel ten feet tall will always trump a woman who cuts him down to size. There’s a reason why the romance genre in fiction is so popular. It keeps a lot of women home alone, lost in dreams that can never come true. Why not put down the books, take off the rose colored glasses, and see the gems that are actually out there. They may be a little rough around the edges and show some of the tarnish of time, but hey, maybe you do too. Remember that old adage that “all that glitters isn’t gold”? Think about it.

Home for the Holidays – Alone

Every year millions of women spend the holidays alone, nursing old wounds, mourning lost loves, and lamenting how each New Year’s Eve they have to watch TV as the ball in Times Square drops down on yet another year.

I’ve been there. Maybe you still are. OK, take a time-out for a little self-pity and then get to work turning “home alone” into “home improvement” and an opportunity to meet someone special.

For starters, clean out your closet. (Yes, you read it right).

Aside from getting rid of the things that just don’t work for you anymore, maybe it’s time to find some space in your closet – and your life – for someone else’s shoes, toothbrush, or books on the table. Get rid of clutter and stuff you never use.

And what does this have to do with meeting someone new? Everything.

When you psychologically prepare to make room in your closet for someone else’s things, you’re also making room in your heart for someone else’s love. Shedding things that don’t fit anymore gives you the chance to think about what does. Who are you now? Who could you be if you weren’t stuck hanging on to the past? Use your “alone time” to reflect on what you will do differently to let love in.

This holiday, as you fill up bags with your past, resolve to look to your future, with someone, instead.