Chapter 6: Adventures in Dating

Roger stood at the head of the table with the carving knife and fork in his hand. He looked down the table and considered how truly thankful he was. His wife sat to his left, her sister to his right. She sat at the opposite head of the table. Some of their children sat at the table with them. Some of the younger children sat at a separate table, since they couldn’t all fit at one table. Yes, they were a large and happy family, but the journey here had not been easy. And The Plan had not helped. Well, maybe a little. After all, it had helped him find her, Roger thought as he looked to the opposite head of the table smiling, and she smiled back.

The Plan was Roger’s blueprint for how he was going to meet and date women. The number one item on Roger’s plan was:

Change support group. People attending a support group for widows are not ready to get involved in a serious emotional relationship. For proof, remember the date with Tina (I wasn’t ready) and date with Pepper (she wasn’t ready).

After his date with Pepper, Roger did not attend any more widows/widowers support group meetings. Instead he started attending singles group meetings.

At the singles meeting he attended, Roger assessed the attendees. The singles group had about twenty-five women in attendance. Roger figured most of the women were between twenty-five and thirty-five years old. But, he didn’t find them very attractive. He also noted that there were about twenty other men there. They looked about the same age as the women.

Instead of joining the singles parent group, in September Roger started attending the Wellington single parents group. This group also had about twenty-five women. Roger estimated their ages between twenty-five and forty. There were also about a half dozen men in their thirties or early forties at the group. Although he didn’t currently have children, no one objected to his inclusion, once they heard about his wife and children.

The second item on Roger’s plan was:

It’s a numbers game, ask out and date as many women as possible.

After about a month in the Wellington single parents group, Roger was ready to start asking women out. At the second meeting in October, Roger approached Ann Tyler.

“Hey, Ann,” He began, as he approached her at the refreshment table. “Are you free this weekend? I thought I could take you out for dinner.”

“Oh, hi Roger,” Ann answered, a bit surprised by his sudden approach. “No, I don’t have any dinner plans this weekend. What did you have in mind?”

“I thought I could take you out on Friday night. Start at Outback and go from there. What time should I pick you up?”

“Hmm.” Ann thought about it for a second and answered, “Six thirty should work.”

Just as he was finishing getting Ann’s address, Roger saw Megan McCormick come into the room. He walked up to her and tried the same approach he used on Ann.

“Hi, Megan. Say, I was wondering if your free for dinner this weekend,” he quietly asked.

Megan smiled and stood there for a moment. She responded, “Gee, Roger. I’m sorry, but I just don’t see you that way.”

“No problem, sorry to bother you,” he quickly said and walked back to his seat.

After the meeting, Roger approached Amber Hilliard with a similar tactic to the other two women. She agreed to go out with him on Saturday night.

That Friday night, Roger took Ann to dinner. Ann was a five-foot seven-inch raven-haired woman with a ten-year-old son and six-year-old daughter. Roger didn’t meet the children that night, as they were with their father. When Roger picked Ann up at her house, he was impressed with the classic long sleeve dress that she wore. It flowed down a few inches past her knees and had a scooped neckline that hinted at her nice cleavage. Her hair fell to her shoulders and was styled to flare outwards at the bottom. Finally, Ann’s makeup was applied with a deft touch that enhanced her natural beauty without distracting from it.

At dinner, Roger observed, “I bet every guy in here would love to trade places with me tonight.”

“And why’s that?” Ann asked, with a coy smile.

“To be on a date with the most beautiful woman in the room, of course,” Roger answered with a smile.

“Flatterer,” Ann’s smile grew in response to the compliment.

“Well, it’s true.”

“I’m sure most of the women wouldn’t mind being in my shoes either.”

“Do tell?” Roger inquired.

“Smart, well-dressed, charming and handsome men are not easy to come by,” Ann replied.

“That’s very kind of you.” Roger paused for a moment before changing topics. “So where did you grow up?” Roger asked next.

“I went to high school in south Miami, in the Pinecrest area.”

Over the course of the meal, they continued with other, typical first date small talk.

Roger enjoyed dinner with Ann. So much so that he asked her to join him for a cup of coffee at Starbucks when they left the restaurant. After coffee, Roger brought Ann home and gave her a tender kiss goodnight, telling her he would like to see her again and would call her soon to arrange it.

On Saturday, Roger went to dinner with Amber. At twenty-eight, Amber was very pleasing to the eyes. She had an even more generous bosom than Ann. She wore a loose sweater that showed her upper chest and tight jeans with various rips in them. Roger could hear Amber’s two and three year old children in the background when he went to pick her up.

Roger took Amber to Chili’s.

“So Roger, what’s it like to be a plane man?” Amber asked in mock fascination, as she leaned forward on her hands.

Roger’s jaw dropped in horror at Amber’s attitude towards his work. He recovered a moment later and answered, “Well, as an aerospace consultant, I spend a lot of time reviewing designs and advising clients on the best materials and manufacturing techniques.”

“Is it fun?” Amber giggled as she asked the question.

Roger sighed in exasperation and answered, “I’m not sure I would describe it as fun. But I enjoy the work and find it challenging,”

“Hey, can we go to a club after dinner?” Amber jumped in, as soon as Roger finished the sentence.

“Umm, let’s talk about it when we’re done eating,” Roger answered calmly.

When dinner ended, Roger took Amber straight home. He took her to the door, said good night and walked back to his car.

After those first two dates with Ann and Amber, Roger awoke on Sunday morning and went for a bike ride. During his ride he reflected on his first week of dating under The Plan. He had asked out three women. Two accepted. Only one of the dates had turned out well, but Roger had doubts about how many more dates he would have with Ann. Considering that the Wellington group only had ten women that Roger thought he wanted to date, he was getting a little concerned that he would quickly exhaust the pool of available women.

Roger thought about Amber. Her attitude towards his work and her choice of clothes showed a clear lack of maturity. Roger realized he needed to pay closer attention to what the women in the group were saying before asking them out. While he loved children, Roger could do without the headaches of the early childhood years. He decided not to date any women with children younger than six.

Later Sunday morning, Roger called Ann and arranged to go out again on Friday night. He suggested that he would be taking her dancing and asked what style of dance she liked. He groaned inwardly when she told him she wanted to go salsa dancing. After hanging up, Roger looked in the phone book to find other community centers in the West Palm area. He found one near the airport and another further south.

On Monday Roger asked out three women, which resulted in two dates. He was relieved when Shani agreed to go out on Thursday night.

On Tuesday Roger attended the first single parents group meeting at the Vedado Park community center.

At five foot five with wavy dark brown hair down past her shoulders, thirty-two-year-old Shani Rasch was just Roger’s “type”. Okay, she was probably the “type” for ninety percent of the adult male population. Roger didn’t meet her children that Thursday night, as Shani had arranged for them to spend the night with their father.

Roger enjoyed talking to Shani well enough. However, more than once during dinner, she hesitated or redirected the conversation when Roger asked a question. When dinner was over, Roger asked Shani to join him for coffee. Refusing to look Roger in the eye and fidgeting with her small purse, she answered, “You know, Roger, I think I’ll pass.”

They didn’t speak while Roger drove Shani home. As soon as Roger pulled up in front of Shani’s building, she opened the door and jumped out of the car. After she got out, she threw the door closed and practically sprinted to the building. Roger looked on, shocked at the clear rejection and wondered what he had done or said to bring about such a reaction.

Roger showed up at Ann’s door on Friday wearing a royal blue long-sleeved silk shirt and black dress slacks. Ann opened the door wearing a long sleeve red dress that fell to a few inches above her knees with large pleats that left room to move her legs freely.

When Roger brought Ann to the car, she frowned and stopped. Roger looked over to Ann, and asked, “What’s wrong?”

“You want me to get into that car in this dress?” She asked, with a slightly irritated tone, as she looked at the Z3.

“I never really thought about it,” Roger responded, as his faced twisted into a confused look.

“It’s hard enough getting in and out of a car in a dress like this with three-inch heels. That car is so low, you’ll need a crane to pull me out. Plus, anyone nearby will get a nice show for their trouble, and I’d rather not put on that show,” Ann said, with a bit of heat in her voice.

“So, what do you want to do?” Roger asked calmly, not wanting to further antagonize Ann.

“Let’s take my car. You can drive,” Ann answered, still a little bit annoyed. She reached into her purse and handed Roger her keys as she led him to her 1992 Ford Escort. “And when we get out of the car, you’re going to have to help me out of the car. It’ll help keep the peep show to a minimum.”

Roger groaned inside with that comment. Ann was getting on his nerves.

After a pleasant dinner, Roger drove them to La Bamba for dancing.

It quickly became apparent to Roger that Ann overestimated her skills. During one dance, Ann did a high leg kick, only to have her plant foot slip and she fell backwards. Roger found himself doing a somersault for the first time in over thirty years, as Ann pulled him down in the process. Later, after working up a sweat, Roger twirled Ann; her slippery fingers lost their grip on Roger’s hand and Ann found herself bent over a table with her skirt up and her thong panties on display. Roger made a mental note to ask future dance partners how experienced they were in their chosen style, before taking her dancing.

While Roger mostly enjoyed his night out with Ann, he just didn’t feel any chemistry with her; especially after starting off on such a sour note with the car issue. At the end of the night, Roger told Ann he had a good time and thanked her for the date but didn’t make any promises to see her again.

On Sunday morning Roger went for a run and reflected on his first two week’s dates under The Plan. The conclusion was disappointing. He had gone on five dates with four women and didn’t plan on seeing any of them again. Last night’s date with Elise Richards was almost forgettable, with one exception.

Roger had known that Elise was well endowed, based on his interactions with her at the parents group. But she had always worn loose sweaters or sweatshirts, effectively concealing her actual size. For their date, Elise had worn a tight white long sleeve shirt and black pants that left no room for interpretation about the shape of her legs. While no expert on cup sizes, Roger estimated that her generous chest was an E-cup.

While sitting at their table chatting, Elise’s eyes suddenly got wide. Roger turned to see a twentyish man with a very surprised look on his face as he stumbled and fell forward. Meanwhile, a bowl of creamy white soup floated through the air, seemingly in slow motion. The bowl landed on the table and a little bit of soup sloshed out. Roger’s relief was short lived as the momentum of the bowl carried it twelve inches further until it tipped off the edge of the table and into Elise’s lap. Elise, aided by some towels from the restaurant staff, worked to clean up the mess in her lap. She spent the rest of the meal fidgeting.

After dinner, Roger took her home and when she invited him in for coffee, he begged off.

Roger had a mixed sense of disappointment and relief at the following Monday’s support group meeting. He actually had to ask out all four of his remaining prospective dating partners to get two dates for next weekend. He wondered if some of the women from his dates had been talking. He still couldn’t figure out what had happened with Shani that provoked such a strong reaction from her, and she wasn’t at the meeting to ask.

Roger’s dates the following Friday and Saturday with Tara Ford and Michelle Cook went well enough that he arranged to go out with each of them again the following weekend.

On Sunday, Mandy came over for lunch.

During her visit, Mandy asked sweetly, “So, Roger, have you been dating anyone lately?”

Roger snorted, then answered, “Now that you mention it, I’ve been on dates with six women in the last few weeks.”

Mandy’s eyes popped open in surprise, “Really! Anyone special?”

“Hmmm.” Roger thought for a minute on much detail to share with Mandy. Then he stated matter-of-factly, “It’s too soon to know. So far, I’ve only been on a second date with one of them. Although, the last two women were promising.”

“This is certainly a big change for you. Where are you meeting all these women?” Mandy inquired.

“Well, you know that I’ve been attending support groups for the last several months,” Roger replied.

“Yeah, but you told me that the last person you dated from a support group, that situation didn’t turn out so well,” Mandy offered.

“Right, plus there weren’t very many women under forty in that group. They were mostly over sixty.” Roger paused briefly, then continued, “So, I found a group with younger women in it. All the women I’ve dated recently came from a single parents support group.”

“Huh. Do they allow you to date other members of the group? Couldn’t that get messy?” Mandy asked.

“Well, if you think about it, they can’t really forbid dating among members. However, they do urge restraint and caution. Like you said, a bad date could ruin the group dynamic. But, when it comes right down to it, one of the objectives of the group is to help the participants get ready for dating again. The end result of that would be to actually date again,” Roger explained in a steady tone to Mandy.

“I see. And how do you like these single moms?” Mandy asked with a small smirk.

“Eh,” Roger shrugged. “Most of them are nice enough. There have certainly been some interesting dates.” Roger proceeded to tell Mandy about some of the misadventures on his dates. He told her about Ann’s ambitious dance choice, Elise’s run-in with the soup and Shani’s abrupt end to the date.

“What did you do or say to her that upset her so much?” Mandy asked.

“I wish I knew. She wasn’t at the meeting last week,” Roger replied with an exasperated tone.

“Did you try calling her?” Mandy continued.

“I called her once and left a message, but she hasn’t called me back. I don’t really expect to hear from her again. It’s pretty frustrating,” Roger told Mandy, with obvious strain in his tone.

“Well, I guess as long as too many women don’t stomp out on you...” Mandy trailed off. Then she started again, “There’s not much else you can do about it.” Mandy paused briefly, then asked, “Have you mentioned all this dating to your therapist?”

“No, I haven’t seen him since January. Why?” Roger responded, puzzled.

“Your approach to meeting women is somewhat unusual, and, doesn’t sound like it’s working. I just wondered what a professional would think of all this,” Mandy replied.

“I don’t think I need to see him right now. If I don’t find a meaningful relationship by new year’s, I may give him a call,” Roger said in a resigned tone.

After a few moments of silence, Mandy asked, “Are you going to join me at Terry’s for Thanksgiving again this year?”

Roger thought about it for a minute. He recalled the interesting conversation he had with Stretch the prior year. He answered, “Sure.”

As they were finishing lunch, Roger asked, “Hey you want to help me buy another car? I took a date dancing last week and she refused to get into the Beemer. She was concerned about getting in and out of such a low car. I think I need something a little higher off the ground and with more passenger room.”