Inside the Dating Scene Follies

Ah, to be single. the moonlight, the cafés, the mystery, the anticipation. The chivalry, the romance, the surprises, the adventures—and, eventually, the happily ever after.

Why indeed? Is her experience typical? With no lack of moonlight and romantic settings along the Gulfshore, we set out to investigate.

While attraction criteria are clearly subjective, we chose to interview women who would, by anyone’s standards, exceed the average: all attractive 30s, 40s and 50s; successful in their fields; some community leaders; and all intelligent and articulate.

Everybody wants to talk; nobody wants to go on the record

One very eligible single woman thought it would be great fun to share some of her experiences. But, she says, "When my girlfriends learned that I agreed to discuss this topic with you, they warned me that I’d end up sounding bitter or desperate."

So we agreed—for the most part—no names. On condition of anonymity, they were free to tell their stories, express their opinions and put the Southwest Florida dating scene on the table. We had focus groups, phone chats and e-mails. We met in the coffee shops and on the battlefield. The stories ranged from incredible to heartbreaking to hilarious. Despite the laughs, though, the outlook seemed so bleak. So in the end we had to give the men a chance to defend themselves.

… asked me to tell him my name once again to save himself the trouble of checking my previous messages.

… said I had a sexy voice and please describe what I wear to bed.

If they get past those first few e-mails and the guy seems normal on the phone, it’s on to coffee or dinner. And the stories get funnier (or sadder, depending on where you’re sitting).

There was the one who …

… paused during dessert to take his Viagra.

… confessed to having an enlarged prostate and asked if my breasts were real.

… asked if he could call me "mom" and I could call him "son."

… took me to his late mother’s home, where everything was exactly as she left it. He asked if I’d like to try on some of Mom’s clothes.

… asked, "Did you see the car I drove up in?"

Men say they want intelligent women, but they don’t, agrees a female real estate attorney.

"I’ve enjoyed flirtations with a few men who, as soon they learned I’m a lawyer, started acting competitive. One man actually said: ‘No one cares about the number on your IQ test. All they care about is the number on your bikini.’ 

"It’s not in my nature to dumb down to accommodate someone’s ego," she says.

"The last woman I’d date is a lawyer," responds a successful lawyer of the male gender. "Women lawyers—if they’re successful—are hard as nails. I want a soft, sensual woman. Men don’t look across a room and think: ‘That woman looks smart—I’d like to have an intellectual conversation with her.’ Do I have to say it? We’re thinking, ‘That woman is hot. I’d like to [make love to] her.’"

Candid enough for you?

"What the women say about men is true, but it’s not just here in Southwest Florida," says this same lawyer, who is a particularly handsome, healthy-six-figure, expensive- sports-car-driving 43-year-old. "It’s true there are very few good guys. The normal ones don’t stay available for long, and those who do either have serious psychological hang-ups or they’re enjoying playing the field. If you’ve got hundreds of millions—and believe me, in Naples, many do—you can do whatever suits your fancy at the time. Plus, Viagra has changed things.

"Wealthy 60-year-old men here date gorgeous 25-year-old women because they can. There’s a nasty carnal reason for that. Women’s sex drive diminishes after 50 or so. I want a woman who always wants to be touching me. Also 50-year-old bodies don’t look as good as they used to, and the harsh reality is that it’s not going to get better. Women are less inclined to be put off by aging men than men are by aging women.

"Men in my age and professional bracket—we’ve got game now. We’re more mature and we’re suave. The women you’re talking about know us already—we can’t impress them. But we can impress the 25-year-olds. If I can play the game with no risk, why not? Can I talk with them? Maybe not, but the sex is good."

Why don’t you just leave?

"I very well may take my belt with its 31 notches and move back to Boston," says Ms. 31 First Dates. Easy for her, perhaps, but not so easy for the top-tier executive of a prominent Fort Myers corporation at the pinnacle of her career. And impossible for the 39-year-old divorced mother of a three-year-old. Under Florida statutes, she explains, the custodial parent must remain in Florida as long as the other parent lives here. "So although I really want to leave, I could be stuck here for 18 more years."

After several years of bad dates or no dates, one very attractive Southwest Florida woman was convinced there was something wrong with her. But every time she went to Arizona on business, she met interesting, attractive and articulate men. Now she has a second home in Scottsdale and a thriving social life.

Are we hearing that there are no ethical, emotionally stable, eligible men in all of Southwest Florida? How about the handsome, well-dressed 50-year-old hotel executive who prefers intelligent women, is chivalrous and romantic, has a delightful sense of humor and is actively looking to settle down with one cherished woman for the rest of his life? "Well," says a close friend, "the package includes a young son who is the light of his life. For most women here, he says, that’s a deal-breaker."

One 20-something single bartender who surveys the dating scene from the other side of an "it" Naples bar says single parenthood isn’t the only deal-breaker for women here. The others, he says, are the lack of an eye-popping financial statement and a garage full of designer cars. "Women my age are chasing money, which means they’re chasing age," he says. "I go to Miami and Fort Lauderdale for my dates."

About the Internet

About that great catch

A matchmaker, perhaps?

An attractive brunette business manager from Naples signed up for a service which, for a fee of $1,400, sets up their busy clients with 15 handpicked dates based on interviews and extensive client criteria. "For me, compatibility is essential, so I specified someone in management who enjoys travel," she says. "I wore a new dress and took care getting ready for my first date. Nearly an hour after the appointed time, the guy showed up, no apologies—with long unkempt hair under his motorcycle helmet. It turns out he is in management—of a garbage collection company—and his travels? All across South Florida! The dating service offered me a free date for my trouble. I said, ‘No thanks, just give me my money back.’"

Reassessing values

A highly visible Naples doctor says she sought and married exactly the man of wealth and position she had always envisioned: "I saw my future husband as a multilingual international businessman who could give me a luxurious life. On paper, it looked great. He matched everything on my checklist. But I didn’t really like him, and I didn’t like the person I was when I was with him. I finally have my priorities straight. I’m not actively dating, but I’m open. The next one, if it happens, will happen naturally."

Nice guys do exist

He’s probably right. Besides his obvious sense of humor, according to the tipster who led us to him, he’s good-looking, successful, self-confident but modest. Married more than 20 years, now single long enough to have put the past behind; his philosophy is "You get out what you put in."

Where are you looking?

"I believe there is a growing number of eligible men here who aren’t looking for trophies," says a charming and successful Naples bachelor in the arts field. "The complaints that your women have are not exclusive to this area. I would say to them, ‘It depends on the kind of guy you’re looking for. If you go to the bars on Fifth Avenue, and the restaurants [known as singles’ spots] … any time you bring a wallet into the equation, you will get results equal to your standards. I would suggest to ladies who go to these places and then say the men are no good, that they put their names in at the art galleries, get invited to openings and places where they are likely to meet more sensitive types.’

"I don’t believe the Internet is the answer. My most satisfying relationships have been with women I’ve met through my work. But you can’t take any location for granted. You can run into your soul mate anywhere, if you just relax and keep your eyes open."

It’s a tough environment

This one’s happily married, but as one who grew up in Naples, returned from college a sports hero and now, at 35, earns six figures in the financial industry, he knows many high-octane singles.

"Naples is a great place to raise kids, but dating here is tough," he says. "Wealth has a lot to do with it. I have a friend who retired a multimillionaire at 34. He was just a kid from Arkansas and suddenly his money was his bait. Not surprisingly,

it attracted the wrong women, and he finally moved away. I have another friend who’s ready for a relationship. He’s trying so hard, making the rounds, but he says women are far more aggressive than they were 10 years ago. I’m so glad I have my wife and family. I wouldn’t want to be out there. If I were, I’d try a singles professional group."

Interesting he should say that.

Young Professionals:

Six marriages and counting

Though it’s the last thing real estate broker Dan Sinclair had in

mind when he started the Young Professionals in Fort Myers eight years ago, six matches have been made in the organization and half a dozen more couples are now dating.

"With so many things going on," he says, "it’s impossible not to connect with people with your interests. We have five softball teams, as well as soccer, bowling, tennis and volleyball teams. We have boating events and wine tastings, and we bring in speakers. We even have a motorcycle director."

Interestingly, one of the least-attended events of the last year was a Valentine’s Day Pajama Party, cooked up and co-sponsored by a local matchmaker. "In all fairness," Sinclair says, "it was a last-minute idea, and we didn’t have time to do the usual advance publicity. Also, it was cold that night, and maybe people didn’t want to come out in their pajamas."

Still, Sinclair believes that successful dating is far more likely through mutual interests than the bar or Internet scene. And he’s not just guessing. He started dating Kim, his wife of four years, after building a friendship through Young Professionals.

Before you ask, the Web site is www.ypfl.com, or (239) 466-YPFL (9735).