My Week Of Flirting With Men

In a recent poll, 43% of you told us that men had a harder time dating than women did — so we put that theory to the test. Here’s how our writer fared during her week-long flirting experiment.

By Jane Ganahl

hen you’re over 50, you have a mixed relationship with flirting. After dating for decades (upon decades), singles tend to be choosier than they were in their twenties; back then, anyone cute with a pulse would suffice for company. Fewer genuine prospects mean fewer attempts at flirting. Also, at this age, you typically no longer frequent some of the singles hotspots of your youth; most of my
I was in dire need of getting my flirtation muscles back in fighting shape.
middle-aged friends wouldn’t be caught dead in a “meat market” scene — or a fern-filled one, either.

The result: your flirting muscles can atrophy. Many times in recent years I’ve had a perfect opportunity to have a spicy interaction with a receptive man… only to choke in the crucial moment. My lack of skills was mystifying to me — in my youth I was deadly at flirting, the envy of my shyer friends. When I was going to college in Spain during the Pleistocene era, my male Spanish friends had a nickname for me: la coqueta, “the flirt.” What had happened to me? I was in dire need of getting my flirtation muscles back in fighting shape.

Thanks to Happen magazine, I got that chance. First they agreed to run a series of polls themed around women flirting with men. Then, armed with the results, I promised to flirt with someone every day for a week.

It was an interesting week…

Friday: A professional sports event
I thought a perfect way to start my week of flirting would be to go to a Giants game. I’m already a fan, and I’ve got the gear and knowledge of the game to show for it. And there are men everywhere at a pro sports event — some of them even my age. Granted, it’s sometimes hard to look attractive when wearing layers to fend off the cold springtime air in San Francisco (or hide mustard stains on one’s jersey), but I thought it was worth a shot.

My friend and I ended up engaged in conversation with two men who looked younger, but were also friendly and funny. We exchanged high-fives when something good happened on the field, bemoaned the Giants’ inability to drive in runs, and shared garlic fries. It was good fun, but things cooled as the game got more heated. It was hard to flirt as the tension rose, and our male friends’ beer intake reduced them from being clever conversationalists to slurring loudmouths.

Lesson learned: There’s a good reason only 13% of respondents in Happen’s recent online poll of nearly 25,000 men and women said that a sporting event was a good place to flirt. Some fun can be had, but it’s really more about the action on the fields than getting any in the stands.

Saturday: The farmers’ market
I am lucky to live in an area that’s rich enough in agriculture that the Saturday farmers’ market is more of a festival than a grocery-buying experience. Live bands play, there are tons of free samples, and attractive men who share my love of good produce stroll around, looking adorable and environmentally conscious with their reusable bags.

As usual, there was a line for veggie tamales. Spying someone who looked like my type of guy at the end of the line, I hurriedly queued up behind him. I asked the man if he’d ever had them before, and he said yes, that they were excellent. Knowing how men love to feel as if they’re doling out useful information, I fibbed and said I had not tried them before. He smiled and waxed rhapsodic about the joys of said tamales… right up until the moment he was joined by his girlfriend.

I tried one more flirtation attempt over by the artichoke stand, but a smile was as far as I got. This, I thought, could be a long week.

Lesson learned: The ambience of a farmers’ market is charming, and you know you’ll see like-minded people there… but it’s hard to strike up a sexy conversation, even when you’re squeezing melons. And even though 44% of the nearly 35,000 men surveyed in our Happen poll said they prefer the direct approach when it comes to flirting, there’s something to be said for striking up a casual conversation. After all, just think of how embarrassed I’d have been if I’d said “I want you” to tamale man?

Sunday: Wine-tasting event
I needed to make a trip to the wine country to pick up some donated cases of chardonnay for the nonprofit I work for, so I decided I’d also use the junket to do some wine-tasting (and hopefully, more flirting). Bad idea! At the winery tasting center, at least 3/4 of the 20 or so people present were coupled up already, and the few unattended men who were milling around appeared to have been there for several days. Hanging over the bar, they spotted me and my friend and made their approach. We braced ourselves for it.

“What’re you ladies drinking?” they asked. We murmured some responses, avoiding direct eye contact. Then the older of the two gentlemen blurted out to me, “I’m a sucker for a pretty redhead,” and smiled blearily.

If I’d found him attractive — or even if he’d been sober — I probably would have been charmed; I always preferred the direct approach (as apparently you do as well, readers). But seeing as this was a one-sided flirtation, we decided to thank the two men for their attentions, and then moved on to the next tasting room.

Lesson learned: Wine-tasting rooms are not the singles bars of the 1970s.

Monday: The gym
Nothing much interesting happens on Monday evenings, so I thought I’d try my luck at my usual Monday morning work-off-the-garlic-fries trip to the gym. I’ve noticed a few men there who have smiled my direction, and I was undaunted by the fact that Happen readers (53% of just over 57,000 men and women surveyed in a follow-up poll) deemed the gym the very worst place for flirting.

The trouble is, at my age, I no longer look adorable in spandex, so I tend to wear sloppy, comfy, cotton-based clothes to work out in. I did attempt to at least comb my hair in anticipation of some possible flirting action going on. A good place to try and flirt is on side-by-side treadmills — assuming
I primped myself way more than I normally would for such an outing.
the object of your affection is not racing or huffing and puffing (or, as it turned out in my case, plugged into his iPod).

I spotted one of the men who had smiled and made conversation with me on a previous day and positioned myself beside him on the next treadmill. I asked him if he’d mind if I changed the TV channel; he said nothing. I waited a while, and then asked again… still nothing. He finally turned his head in my direction and noticed that I was there. He smiled and pulled a tiny earphone out of his ear.

“How’s it going?” he said, and then turned off his machine and hopped away. How is one supposed to flirt in a time when electronic devices are the focus of everyone’s attention?

Lesson learned: Gyms stink. Literally.

Tuesday: An artistic event
My day job is with a literary festival, so I had high hopes that Tuesday night’s event — a book-release party at a famed bar — would throw me together with like-minded people. (Make that: men who were my age.)

Walking in the door, I was not disappointed. Standing in the crowd was a sixty-something movie director I’d met several times over the years and always had a secret crush on — but I’d never acted on it because he was married. I gave a quick glance at his ring finger, which was currently empty. And I also noticed that he was standing alone. I reintroduced myself, we got to chatting, and that’s how I learned that his wife had died two years earlier.

When one’s aim is to flirt, this kind of information can be a buzzkill. (And it happens more often the older you get, you know.) The direct approach (“I’ve always had a crush on you”) would have been inappropriate in a situation like this, so instead I suggested that he might want to participate in the festival this year. He gave me his card and asked me to get in touch with him. We both smiled… we felt a connection!

Lesson learned: Work-related events can be the perfect spot for flirting — providing that it doesn’t compromise your job, and especially if you’re passionate about your vocation.

Wednesday: Hanging out in a café
I sometimes go to a café in my town to meet a friend who’s a fellow writer so we can enjoy some shared writing time together. This time I decided to go solo and plant myself somewhere visible to see what would happen. Much like I did throughout the week, I primped myself way more than I normally would for such an outing. (I realized during the course of the week just how little attention I pay to my looks — which could be one reason my love life has been in the tank lately.)

After an hour, an attractive older man sat down at a table across the room to read the paper. I kept looking up from my laptop at him, and eventually, our eyes met. Recalling that 64% of the 39,000 men and women surveyed in March said that the flirting technique men find most charming is “a smile and flirty look across the room,” I screwed up my courage and gave him a sly (but very direct) grin. He looked a little bit taken aback, and he even glanced around to make sure I was smiling at him and not someone else, but then? He smiled back. Pleased with the result, I went back to my writing. Both of us sat for a while, eventually exchanging another smile or two during our time there. But after an hour, I had to leave — and while I considered walking up to him and dropping off my card on the way out, I ran out of courage.

Clearly, I still need a lot of practice.

Lesson learned: Cafés can be casual and relaxed places to go, but chatting is often not part of the café experience, so beginning a conversation with someone you don’t know can be awkward.

Thursday: Volunteering
Every morning I perform volunteer work by helping feed some homeless kitties across the street from my house. They live by a parking lot, and I have helped out these last 18 months with feeding, trapping, spaying and neutering, and finding homes for those who are adoptable. It takes time out of my busy day, but also fills my heart with joy — just as any act of devotion does.

While pondering what to do with my last day of flirting, I went to the feeding spot in my sweats, hair up in a twist, and makeup-free. As I was serving a plate of food to three hungry cats, a nice-looking man walking his dog passed by on the sidewalk. Seeing what I was doing, he said, “Aren’t you nice?” and smiled. After a brief conversation, we traded numbers. I’m not sure whether he’ll call, but I was pleased that he was clearly drawn to who I am at heart, not my attractive looks — or lack thereof.

Lesson learned: Perhaps there is something to the old quote by Arthur Buddhold: “Follow your passion, and success will follow you…”

Final thoughts
Shared passions seemed to be the key that led to successful flirting for me this week. I also learned that if you don’t consciously think about flirting, you can’t do it effectively! If you’re middle-aged and want to exercise that flirting muscle, put yourself in a setting where making casual conversation is both expected and welcome — not a gym, café or even a wine bar, apparently. When you’re over 50, it’s no longer considered cool to seek out romantic partners in bars, while hearing live music, or dancing out on the town. That means we need to get more creative and stick closer to activities that mean something to us mid-lifers. If we feel like it, there’s no reason we can’t continue flirting until we’re 90!

For a man’s take on the week-long flirting experience, read My Week Of Flirting With Women.

Jane Ganahl is author of Naked on the Page: The Misadventures of My Unmarried Midlife, editor of the anthology Single Woman of a Certain Age, journalist of two decades, and codirector of San Francisco’s Litquake literary festival.
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