What's a Single Woman to Do?

From the front lines, listen to those out looking for Mr. Right—or even just a good date.

When Frank passed i thought for sure there would never be another man in my life,” says Paulette Fischer*, a 73-year-old Chicago transplant who now calls Sanibel home. “I felt the same when Malcolm passed. Ha! … (But) I’ve been alone for a few years now and it seems harder than ever to meet a man. And I want one!”

This may come as a shock, but being a single woman looking for love in Southwest Florida poses some challenges.

“Let’s just say the singles scene seems to suck for ladies my age, as we women are 4-to-1 to men,” says Michele Eddy, with a laugh.

Is that true? Probably not. Does it feel true? “Hell yes!” says every single woman in Southwest Florida.

Having been widowed more than 10 years ago, Eddy has begun to be proactive in looking for a significant other. From using online sites to being fixed up by friends to even hiring a professional matchmaker, Eddy has gone above and beyond to find what she’s looking for—to no avail.

“I’m thinking I’m either hard to match—wonderful as I am—or this is a geographically undesirable area for me,” says Eddy, who splits her time between homes in Fort Myers and the Panhandle. “(Perhaps) my prince is riding his white horse somewhere else? Maybe I should be matching people geographically first. I know I adore Southern men.”

But her story isn’t an anomaly. In fact, talk to virtually any single woman over 40 in Southwest Florida and you’ll hear a similar story: multiple women for every man, unresponsive online matches, a shallow dating pool, and, of the relatively few dateable men around, poor manners and an understanding they are a hot commodity.

“They feel like they don’t really need to put any work in,” says Catherine Clarkson*, a 58-year-old divorcée who’s lived in Naples since 2010. “They don’t call when they say they will, they don’t plan ahead when you actually do get a date, and they don’t seem to own a real shirt anymore. Apparently you move to Florida and all you can have in your closet is T-shirts and polos.”

She actually had one suitor show up to their first date 20 minutes late wearing a filthy Hooter’s shirt. “He said he came straight from fishing because he lost track of the time,” Clarkson says. “He smelled like bait, then took me to a seafood restaurant. I’m a vegetarian. He knew that. It was on my profile!”

Things could have been worse: He could have seemed perfect from the start. Marla Ottenstein (pictured), owner of Professional Organizer Florida and the writer of the Get Organized column in the Naples Daily News, met a man who appeared to check off every requirement on her list of wants. He was tall, handsome, smart, well-off, well-dressed, well-read and well-traveled. In fact, during their first date he mentioned he had traveled around the world four times just that year. “I asked him if he went anywhere interesting,” Ottenstein says. “He said, ‘Not really.’ After being pushed, he came back with, ‘Well, Easter Island.’ ‘Well, that’s interesting,’ I said. And he goes, ‘I was only there one hour. I never left the airport.’

“It turned out he was only interested in becoming part of the top 5 percent of a frequent flier top-tier program. He never did anything. Just flew from place to place building points,” Ottenstein adds. “I actually went out with him a total of three times because I thought I was missing something. I couldn’t believe somebody could be this boring.”

It turns out they can—in part because they don’t have to put out much effort. Seems things on the other side of the chromosome find a dating pool that’s much deeper.

Which explains a date Marie Schantz* had a few years ago. She met a charming, good-looking man at a speed-dating event. They were enjoying a lovely first date, finished dinner and decided to keep the night going with drinks at a nearby bar. Within minutes another woman came up to her date to say “hi” and introduced herself to Schantz. The man got a bit awkward but kept the date going, but the woman never left them. “It turns out he had met—and slept with—this other woman the night before,” Schantz says. “So, it was our first date and their second.”

And while that seems to suggest the women of Southwest Florida should lower their expectations, the opposite is true.

“Men don’t have to pursue women anymore because women are chasing them all over the place,” says Joanna Simmons*, a 60-year-old widow who moved to the area seven years ago from Michigan and bemoans the use of texting in the dating arena. “I can’t believe they think that’s appropriate. Do not ask me out via text message. If you don’t have time to call me, you don’t have time for a relationship,” she says.

But while the phrase “Beggars can’t be choosers” rolls off the tongue easily, the women of Southwest Florida are definitely not beggars. Many have grown accustomed to getting what they want when they want it and aren’t about to settle now.

As a well-heeled bon vivant, Eddy meets plenty of men, but so far none have had that adventurous spirit she’s looking for. 

The same can be said for Stephanie Rogers*, a 50-year-old philanthropist who’s been divorced for several years and struggles to find local men of any caliber who hold her interest. “Dull, dull, dull,” Rogers says. “But I’m not going to settle. I know what works for me and what doesn’t. … Worse yet, Naples is a very married town.”

And there’s the rub. Singles in the area are overwhelmed by couples, making their situation seem all the more, shall we say, desperate? No wonder women think they outnumber men 4 to 1.

“When you speak to women they may think that that’s true,” says Debra L’Heureux of My Top Matchmaker matchmaking service. “They’re just not meeting the gentlemen. It’s just that the gentlemen are on the golf course or playing tennis or boating and they’re just not coming in contact with the right gentlemen.”

Well, that sounds reasonable. Statistics show that the ratio of women to men in Lee and Collier counties is approximately 51 to 49 percent. So there are more women, but not by much. And those statistics don’t break down single women of a certain age to their male counterparts. So the truth is we don’t really know just how many single men there really are in Southwest Florida—could be hundreds of thousands or, as Clarkson says, “there are 15.”

But even if the lack of actual single men isn’t a problem, the lack of “qualified” men certainly is. Let’s face it: Many single women in this area are in a financially secure place; they’ve either made money on their own, been left it by a deceased spouse, or married well and divorced better. Now they’re at a place in their lives where they recognize they need a man who can keep up with them—both emotionally and financially. For some, if guys don’t have the wherewithal, there’s a serious hesitation to even bother.

It seems to be a prerequisite on both sides. “Some of these men have split their fortunes—sometimes multiple times,” Simmons says with an understanding tone. “They don’t want to buy someone another house, another car.”

“The people they’re meeting are not serious about a relationship,” L’Heureux says. “There are a lot of players out there that are not serious—are not relationship material.”

And then there’s the elephant in the room: Many single men are looking for younger women. (Insert gasp here.) “Age is a challenge, and I don’t know why,” Simmons says. “I’d like to hear this from a man’s perspective. Are they broken from former relationships and think that if they go younger they’re going to have better success? Is it that they feel that older women are boring? When you’ve been married for 30 years, that happens. I hear that from a lot of men: ‘My wife didn’t want to.’ Whether that was go here, play golf, go boating, travel, whatever.”

But while the mystery of why men would be interested in younger women has some perplexed, others, such as the matchmaker L’Heureux, recognize there are still some good ones out there.

In fact, it’s L’Heureux’s job to find her clients just the right match painlessly and without all the drama. And, not surprisingly, she’s busier than ever.

For her art, Simmons has had some luck with Selective Search and, another matchmaking service, and though neither connected her with the man of her dreams, they did match her with suitable men she was interested in. “I do encourage women to get involved with some of these more upscale dating services,” Simmons says.

Then again, her bar might have been set low when she discovered at least one of her former dates could be found on the website, a website that serves as a warning to others. Yikes.

Still, she’s hopeful about the future.

As is Ottenstein. “I’m actively dating—but I’m not searching,” Ottenstein says. “I let people know. You’ve got to tell people because a lot of times people don’t know. A lot of times people will assume that I’m too busy, but I’d love to meet that special someone.”

But not just anybody. She wants an actual man who plans dates and picks up the phone and brings flowers. A guy who has a lot of self-confidence, she says. “I’ve always known what I want. I’ve always had direction. I’m someone who’s focused and goes for the brass ring. But I think a lot of men in Southwest Florida don’t know what they want. … I think Southwest Florida has become a place where people come to heal,” Ottenstein says. “To start a new life after death, divorce, end-of-life parenting—and we’re all searching for that right fit.

“It’s true, Naples is a tough town for singles,” she adds. “But you have to put it out there that you’re looking to meet a quality person with similar values and interests. And always stay positive.”

After all, nobody can prove there is only one man for every four women.


Women’s Dating Tips

OK, so things aren’t perfect for single women in Southwest Florida. But the women we interviewed are, in fact, still positive about the future and finding someone to share it with. Here are some thoughts on what sort of advice they give to other newly minted single women who’ve found themselves.

“I’ve heard people say that they need someone in their life to make them ‘whole,’ but to me, that’s a disaster waiting to happen,” professional organizer Marla Ottenstein says. “What really works is when two ‘complete’ people come together.”

“Get involved, take great care of yourself, think of yourself first, do the things that you love,” Simmons says. “Get involved in charities, the communities; don’t stay home.”

“If you’re in a grocery store and you see a handsome man, there is always an easy way to say, ‘Oh, what choice of bread do you like?’” Clarkson says. “I always ask, ‘Are you married? Where’s your wife?’ because there’s a lot of that down here.”

“Don’t make it about meeting a guy,” Simmons says. “Make it about being happy. When you’re happy, people see that.”

“There are more ways to meet somebody than ever before,” Schantz says. “Speed dating, meet-up groups, online dating, etc. But I still think the old ways are best: friends, church groups, civic organizations. I’ve not met a single man sitting home watching TV.”

“Have a lot of interests,” Ottenstein says. “Play tennis, entertain, read, travel. Go see your friends. Make a point of doing things.”


Guys Gone Wild

Oh my God, it’s great!” says 55-year-old David Francher*, regarding the dating scene in Southwest Florida. A fit, silver-haired entrepreneur from Minneapolis, Francher splits time between his new home in Bonita Springs and his place up north. Divorced with adult children, he is the prototypical single male. And he plans to stay that way for the time being.

“Every time I come down here and go out for a drink or to an event, I meet someone new,” Francher says. “Why on earth would I want to jump into a relationship? I’m having too much fun. I get to do what I want to do when I want to do it with whomever I chose to do it.”

And it seems his choices are endless. He described feeling like fresh meat his first season here. “A couple women actually said that to me,” he muses. “I get asked to do things more down here than when I was single and in college.”

As to why older men seem to be gravitating toward younger women, 61-year-old Frank Navarra* seems confused. “I don’t understand the question,” he says, mockingly. “I’ll tell you what: If I could’ve put the mind of my first wife into the body of my much younger third, I probably wouldn’t be looking for Mrs. Four right now. … I’m kidding. There’s no way I’m looking for No. 4.”