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His and Her Nightlife Diaries

We’ve heard the stories of how tough it is to be single in Southwest Florida, so we decided it was time to find out what’s really going on in the restaurants, bars and dance clubs. Would we find them filled with gold-digging divorcees and less-than-dashing scoundrels? Are there any good guys and gals out there looking for people like themselves?

We sent Jess Fisher, 50, and Mandy Osborne, 37, to various hot spots along the Gulfshore. Here’s what they found after several weekends out on the town.

His Story
Hits and Misses at Bistro 41
Eager to find a new romantic interest, I journeyed to the intimate Bistro 41 at the Bell Tower Shops on a rainy Saturday night. I spotted a 30-something woman seated at the bar eating alone. I ordered a drink, and we smiled at each other. I liked her look until I noticed a piece of calamari dangling from her lower lip like a hanging chad. I thought about mentioning it, but decided instead to inquire about the taste of the food.

"It’s really good," she said. The chad disappeared.

We exchanged pleasantries, and I learned her name is Jamie, visiting from Phoenix on business.
I glanced at the muted, flat-screen television above the bar, and saw a close-up of an aging political commentator whose pancake makeup appeared to flake off. Jamie said she didn’t care about politics, and I immediately agreed. We then talked about places we’ve been, especially Hawaii. I thought things were moving in my direction when she mentioned she was going to a movie after dinner.

She was amiable, pretty and single, so I suggested she be my guest. She paid her bill, gathered her things and left without me. I guess she hadn’t asked me any direct questions for a reason.

Getting Creative at Cru, Blu and Cin Cin
It was 9:20 p.m. when I arrived at Cru. The outside bar was active with young people. Inside, it was crowded. The pulsing music eliminated my disappointment about Jamie. There were six or seven 20-something "chirpies" seated at one table, but they were much too young for me.

I sat at the far end of the bar, and a little later, two gorgeous women—one blonde, the other brunette—made an entrance. The blonde was dressed in a very short, tight-fitting white skirt and a cleavage-enhancing, white sequin-studded top. The brunette wore a short black skirt and a revealing burgundy top with silver studs. Both had on 5-inch heels and sported bright red fingernail polish.

They sat down at a high table in the center of the room and ordered drinks. I made eye contact with the blonde. She smiled brightly. Then, I made eye contact with the brunette. We smiled at each other. After 20 minutes, they were still alone.

The blonde stood up, adjusted her skirt and paraded past me. She was definitely too young for my taste. I caught the brunette, who looked older, watching my reaction.

I asked my barkeep about the two ladies. Over the loud music he said, "I see them once in a while. I think the blonde might be a shrimper."

"A shrimper?" I said. "Wow, she must own the boat."

A short time later, the brunette pulled out her credit card. I felt out-of-my-league, but it was time to move before they left. I introduced myself and said they were the prettiest women I’d seen all evening.

The blonde, Amanda, proudly said Lisa was her mom. Lisa didn’t look a day over 35. I asked if it was true, and she said, "Yes, she’s my 26-year-old daughter," and then added, "I’m 46."

I was surprised that a woman would volunteer her age. I felt some chemistry and said, "Well, since we are revealing secrets, I’m 50."

I asked them, "Do you find men too intimidated to approach you?"

Lisa laughed and said, "Sometimes."

"What is the worst thing men do when they approach?"

"Paws. They put their paws all over me," Amanda said.

"How do they touch you?"

Amanda put her hand on my shoulder and then gently touched my back. "Like this," she cooed. The caress felt really good, but I turned my attention to Mom.

I looked into Lisa’s eyes and said, "What is the worst pickup line you ever heard?"

"You ever hear of the Flintstones?" she said.

I went blank. Then she said, "Well, baby, you make my bed rock."

We continued to talk, and I became convinced my soufflé was rising. Then things really heated up.

Amanda looked at me and said, "We are going to Blu. Want to join us?"

I blinked and said, "I’ll be along in just a moment." I sauntered back to my spot at the bar. I took a swig of my vodka tonic and bebopped my head to thumping rap music.

"Hey, you did really good," the barkeep said.

"I’m going to meet them at Blu," I said. "But, I’ve got to tell you, I don’t think she is a shrimper."

"A shrimper?" he said. "No! I said ‘stripper.’"

As I considered this new revelation, I also realized there were three Blus. "Which Blu did they go to?" I asked in a panic.

The barkeep calmly removed my hand from his lapel and said they probably went to the one on McGregor in Fort Myers.

Blu is a trendy sushi place with a New York City atmosphere, but tonight there were no crowd and no shrimpers—just a few people standing around the bar and a DJ spinning records.

Not to be deterred, I walked to Cin Cin, where a large cluster of people stood outside contemplating the merits of smoking in the rain. Inside, dancers packed in tight hopped to the sound of a karaoke singer wearing a small, white fedora.

I looked around for the mother-daughter promise, but only saw a passing acquaintance. I noticed he was with a new lady. He wondered aloud why I was out alone. I thought about how great it would be if my new friends appeared—but it was not to be.

Looking for Love at Bar Louie and Blu Too
Encouraged by the "promise," I drove 40 minutes to another Blu at Gulf Coast Town Center. The bar was full of good-looking young people milling around. Techno music pounded, and I got into the groove, but no one else was dancing. I saw two interesting-looking women in my age group seated together. I walked by them twice, but they refused to make eye contact with me.

I did not find my new friends, so I walked to Bar Louie across the way. Hip music greeted me at the door, along with a spill-out crowd of young people. A tall, Hulk Hogan type, dressed in black, stopped me at the door. He wanted to see my ID.

"Dude, I’m 50," I said, as I presented my driver’s license. My suave use of young people’s lingo eased the friction, and he waved me inside.

It’s a huge place, and it was full. I wormed my way through the crowd on the lookout for women close to my age. There were lots of suggestively dancing chirpies everywhere. I couldn’t get to the bar, so I stood near the raised dance platform along with a few guys my age who looked like me—lost, dazed and confused.

I returned to Blu in hopes of talking to the two women I’d seen earlier. I sat at the bar and soon one of them stood next to me. I introduced myself and asked her name. She looked at me and curtly replied, "Marla." No smile. No eye contact. No hope. The bartender brought her drink, and she walked away. I called it a night.

Making a Move in Downtown Naples
It was cold, and I wanted a bulked-up look, so I wore two T-shirts underneath my dress shirt. I walked into McCabe’s at about 8:30 p.m. It was crowded outside and standing room only inside. I looked around and spotted two gals I liked.

I meandered close so I could read the message on their T-shirts: WINE PATROL. That provided a witty idea to break the ice: So, just what are your qualifications to be Wine Patrol?

We made eye contact and smiled. I continued with my bar walkabout. Lots of people, but only the Wine Patrol held promise. When I returned, they were speaking to a guy. I pressed onward—no sense in dealing with authority figures and another man.

I crossed over Fifth Avenue to visit Vergina. The dining patio was full. Inside, it was party time, starring an upscale crowd. A karaoke singer belted out Michael Jackson’s Don’t Stop ‘Til You Get Enough.

The lighting was perfect, the music great, and the crowd polite and friendly. I felt warm and comfortable in my Donna Karan corduroy blazer. I noticed two elegant ladies seated at the bar across from me. One had short auburn hair and wore a black, tight-fitting blouse featuring large gold buttons. Just my type.

I looked around, sipped my drink and soaked in the buzz. An interesting threesome made an entrance. The bleach-blond guy had the sides of his hair combed forward and the top combed back. I figured he was a hairdresser. He was accompanied by two attractive women, one of whom might be his sister. A possibility.

My gaze returned to the two elegant ladies, and I thought about possible ice-breakers. The brunette smiled at me, and I smiled back. The barkeep moved between us. A moment later she reappeared, and our eyes locked again. I lip read, "Want to dance?"

I said yes and flashed a thumbs up. I’d been inside about 12 minutes.

Meredith, my lady of the hour, wore black satin capri pants and strappy red heels. I grabbed her hand and led the way to the dance floor.

We danced next to an older couple who acted as if they already had a room. Their embrace was far more seductive than the chirpies’ dancing at Bar Louie. Meredith and I danced to a couple of songs and returned to the bar. She said, "I always talk with someone who makes eye contact." I’m glad she did.

She inquired about me. Things were getting interesting. I looked deep into her green eyes and said, "I’m a writer. But I need a new dictionary because I ran out of words." She laughed, and told me I was a comedian. I learned Knoxville was home, but she wintered in Naples.

We danced again, and I began to perspire lightly. It quickly turned into a global warming sweat that broke out on my forehead and trickled down my right temple. Meredith gestured to the perspiration over my upper lip. I momentarily panicked and thought, "Why did I wear two T-shirts and a jacket? This is bad."

Meredith smiled and handed me a napkin. To deflect my embarrassment, I claimed I sweat when I lift weights.

"I thought you were nervous," said Meredith. She laughed, but strangely, I felt relaxed. It was the compassion in her eyes.

To cool down, I rolled up my sleeves, which revealed my ordinary Rolex watch. I pointed at her diamond-encrusted, solid gold Lady Rolex. Her watch displayed a different time than mine.

I said, "That’s the problem with these cheapo watches—they don’t keep accurate time. May I buy you a drink, Meredith?"

She laughed, said yes, and I escaped the sweat box.

A blond-haired chap who looked like Ringo Starr took the stage and sang Mustang Sally. The dance floor went wild. I asked Meredith if she knew him. She didn’t.

I asked her to dance, and we joined the surging crowd around the stage. I asked a woman next to me about the singer. She turned, her face only two inches from mine, and proclaimed, "That’s Tommy Cochran!"

I had no idea who the singer was, so I said, "Who is he?" She looked at me as if I were from Planet X. I pulled Meredith close and whispered, "That’s Tommy Cochran?" I felt the urge to kiss her, but the groupies jostled us, and the moment passed.

We returned to the bar, and she ordered me a drink. The DJ, sounding just like the real Lou Rawls, started singing You’ll Never Find Another Love Like Mine. I again leaned in towards Meredith, but the barkeep interrupted with our drinks. Then she asked if I had a girlfriend. I said I did not. But skepticism remained in her eyes.

A short time later, the overhead lighting came on. The bar was still full. But Lou had stopped singing, and Cinderella’s carriage awaited.

I walked Meredith to her car, and I kissed her softly on the cheek. We said good night, and I closed the door. The scent of her perfume lingered.

I went back to Fifth Avenue and into Yabba’s. Although it was well after midnight, a large, young crowd enjoyed dancing to the rap music.

But I missed the smooth, soulful style of Lou and the beautiful Southern belle. It was time for me to go home. I walked slowly to my car, thought about Meredith and started humming, "You’ll Never Find..."

Her Story

Getting Started at Café Lurcat and Snapper’s Night Club
Friday night began as it often does—I made plans to meet a girlfriend for a glass of wine at Café Lurcat. It’s a great place to mingle, and you see some of the same people every week.

The men range from doctors and businessmen to young guys in the service industry—and let’s not forget the Naples trust-fund folks. The crowd is usually well-dressed, and on the occasions that I’ve been there alone, people were friendly enough to welcome me into their group for the night.

On this particular evening, I found my friend talking to a guy I thought she knew. I quickly realized that this was not the case—he was definitely fishing. She wasn’t taking the bait, so we moved away from him.

Our new "friend" caught up with us a bit later. From our chilly reception, he finally realized his fate. "So, both of you are about to blow me off at the same time, aren’t you?" We sidestepped him to chat with some acquaintances. We were getting the scoop on the next place to go.

We made quite an impression on one rather intoxicated gentleman who so badly wanted to impress us that he bought the entire crowd a drink. We could hardly understand a word he was saying, so we bailed.

My friend decided to go home since she had an early engagement in the morning. Not ready to end my evening, I met up with some other friends. Since the dance club Sway had recently closed, we were contemplating where to go next.

The winning choice was Snapper’s Night Club. It is close to Fifth Avenue and is, well, interesting. Although it is known as a gay club, it is hetero-friendly. The cover is only $5, the drinks are inexpensive, the music is good and there’s a fun drag show to boot. What more can you ask for?

After the dramatic lip-synching performances, we danced what was left of the night away on the uncrowded dance floor.

Sway With Me
Sway reopened a few weeks later, and once the crowd picked up, we started to dance. Our little social group fluidly intermixed with other groups, and then reformed on the dance floor to compare notes on who we met. As a group of single women, we attracted a bit of attention and had lots of guys joining our circle to dance with us. Any attempt to divide our group was thwarted, as men often underestimate the power of a ladies’ night out.

Getting into the Groove at Bice Lounge and Paddy Murphy’s
Upon entering Bice Lounge, an intimate club located behind Bice Ristorante on Fifth Avenue, I learned that I had just missed the free salsa lessons offered from 8 to 9 p.m. There were a few couples and single women dancing, and the scene started to pick up around 10 p.m.

As I sat at the bar, a group of salsa instructors from a local dance school entered and took over the dance floor with some impressive moves.

A man I dated a year ago came in with some of his family, which only confirms how small Naples is. We chatted a bit, and then I was asked to dance by someone who clearly knew how to salsa (maybe one of the instructors?). Although I am somewhat familiar with the dance, I was admittedly out of my league. He was very gracious, however, and I had fun getting out on the dance floor. At around 11:30 p.m., I was ready to move on to something different.

I arrived at Paddy Murphy’s and found quite a few friends already there. There was a musician singing classics, which makes for a fun evening. There is nothing like good, spirited singing to end a night out.

After Bice Lounge, I was itching to dance, so I found a few willing partners to join me on the small dance floor near the dart boards. I quickly learned that you have to be careful with whom you share your affections in this small town. I was quickly dismissed by a female acquaintance who threw me a scathing look, followed by an, "OK. We’ll see you later" (in a tone that clearly indicated that seeing me later would not be a good thing). She mistook my jesting and, well, OK, my flirty nature, as an attempt to steal her interest of the evening. My bad. I wasn’t trying to compete with anyone.

Since the singles scene is so limited here, people can get a little territorial. It also seems normal for past dates and current possible interests to all show up at the same place, which requires a good sense of humor and a bit of social grace. As a friend of mine describes it: Going out in Naples is a race to look the trendiest without trying, the most available without being desperate and last, but certainly not least, the least interested but the most interesting.

My friend’s ex-boyfriend and I had an interesting conversation about how communication between the sexes has become more difficult to interpret now that so many people rely on text messaging instead of calling. Without hearing a tone of voice and without complete sentences, it can be tough to determine what sentiments are intended. But even with the things that work against us singles in Naples, I still enjoy my time out because it all essentially comes down to attitude.

As I said to a guy who was concerned with his lack of finesse on the dance floor: Sometimes you just have to be willing to put yourself out there and have a laugh.

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