Funny Internet Dating Stories (Part 2) Rich and Rude Randy

This is Part two of a series of funny internet dating stories about Sara's dating escapades. This story is so hilarious and surreal that you might think I made it up. Let me assure you that I did not make it up .. Everthing I write about her dating experiences are absolutely true.

On Sara and Randy's first date there was attraction and hope. On their second date things went from bad to worse, as in a comedy of errors ... an unbelievable account. Yet - I assure you once again, there is no embellishment of the situation - it happened just as I have written.

The conversations between Sara and Randy began as light and entertaining. Since Randy lived on the other side of the U.S. there wasn’t much chance, in Sara’s mind, that she would date him. As they chatted frequently Sara got the idea that Randy had a good job and was stable financially.

Out of curiosity and as a precautionary measure Sara googled his name, his business and his house address. All of the research seemed to verify that he was who he said he was. His house was exceptionally beautiful, it was very large and included an outdoor swimming pool. "Yes," thought Sara, "This man looks to be financial stable." Feeling fairly satisfied with what she found on the internet she continued to communicate.

Over a period of months they chatted frequently.  From a distance Sara began to grow very fond of Randy. He seemed to have a big and caring heart. The day came when Randy asked her for a date. Sara contemplated the pros and cons of dating someone who lived so far away from all her friends and family but her curiosity won out and she agreed.

In preparation for their date and because Randy would need overnight accommodations, Sara gathered the names and numbers of some local hotels and sent them to Randy. She carefully chose a nice restaurant for a place to meet.

For her first date Sara was meticulous thinking about dress and appearance.  She too time to pick out a lovely light rose sweater which complemented her fair skin. Sara does not wear alot of Jewelry, but what she has makes a statement.  She chose her diamond necklace and earrings.  As she was applying the final touches to her hair and face she contemplated how things would go.  Before heading out the door she chose to spray a sweet, light fragrance sparsely rather than choose an alluring, come hither perfume.

Sara reached the restaurant first. As she sat in her car waiting for his arrival she felt a mixture of anticipation and anxiety. She spotted the car and watched carefully as Randy pulled in. The door of the Grand Am opened and Randy stepped out. He looked distinguished as he walked toward her car. He was quite tall with thick dark hair that curled in the back and around his ears. "Very nice," thought Sara as she noticed how attractive he looked in his khakis, rich brown twill sweater and loafers…Inwardly Sara was smiling and thinking “Just my kind of guy,”

Randy greeted Sara with a hug and a warm smile. “So, we finally meet Miss Sara,” Randy said as he continued looking into her eyes, he said, “You are really much more beautiful than your picture reveals.” “Why thank you Randy,” Sara replied, feeling suddenly shy. Walking toward the restaurant, Sara observed Randy’s self assured stride. He opened the door and led Sara into the restaurant. As the waitress led them to the table Sara noted the candles and flowers adorning each table ... "very romantic," she mused. He ordered their dinner and took charge of seeing that Sara was comfortable and received everything she wanted that evening.

As they talked Sara began to relax and enjoy the attentions of this man. This first date was going very well.  Randy seemed solid and dependable. He had large well groomed hands; His facial features were strong. He had well worn smile lines creasing his cheeks and at the corners of his eyes. Sara's thoughts drifted as she thought about how far he had driven just to meet her.  She also thought about the fact that they only had two days to spend together. 

As they were finishing dessert Sara asked Randy where he was staying. Randy replied, “Oh I need to find a place.” Sara was taken back and felt some discomfort as she wondered why he hadn’t made the arrangements.

After dinner Sara rode with Randy to one of the local hotels. Randy approached the clerk and asked for a room. With a look of regret the hotel clerk said, "Sorry sir,there is no room, the hotel is booked full." It was a tourist weekend. The hotel clerk advised them that all of the local hotels were full. Sara walked quickly to the car wondering what he was going to do. She didn’t have to wonder long because Randy seemed to have a plan. He began “Ya know I threw a blanket and pillow in the car when I left; I can just sleep in the car in your driveway.” Sara was stunned by his words but she honestly did not what to do. It was a ludicrous idea for him to sleep in her driveway. Sara felt she had no choice but to offer her house. Randy readily accepted her offer.

As Randy drove Sara to her car she wondered what she had gotten herself into. Thoughts began racing through her mind, "Am I crazy?" She didn't even really know this man ... but what choice did she have. After leading him to her house, she welcomed him inside by saying, “Come on in and I’ll fix you a bed on the couch later.” They settled in and decided to watch a movie together. It was a movie Sara had seen before but Richard seemed to relax and enjoy it. Afterwards Sara was quick to makeup up his bed, hand him a set of towels and then excuse herself to go to bed. Sara didn’t rest well that night… thoughts and visions of murderers, rapists and thieves danced through her head.

She woke up early the next day exhausted. Sara struggled to get out of bed and on her feet. Once up she grabbed her pink robe and fuzzy slippers and headed toward the door, smoothing her hair as she went. She opened the door quietly and peeked out. Randy was awake and working on his computer. His mouth broke into a wide smile when he spotted Sara standing there in her fluffy robe. “Good Morning Sunshine.” He said cheerfully. Sara couldn’t help but smile back. “Good Morning, did you sleep well?” she replied.

That day was filled with walking and chatting as Sara showed Randy around town. Sara lives in a tourist town and there were many shops to take him through. As they strolled the streets she found herself relaxing and enjoying his company. When Randy left for home Sara felt good about the conversations they shared and the time they had spent together. She decided that she would like to get to know him better.

During the next few weeks Randy called, emailed and texted Sara frequently. At first it was fun and she looked forward to hearing from him. But during the third week she was beginning to have some questions about his attitudes and heart. Sara was picking up some expressions that she thought to be a bit judgmental. Oh dear Sara, if only you had only known....

The second date was arranged by Randy after the third week. He called Sara to let her know that he had made plane reservations for a three day trip. Sara felt uneasy that Richard had just assumed she would be available. As it happened she did not have plans and now felt stuck because he had already purchased the tickets ... “he is very presumptuous,” she noted.

Randy would be arriving on Friday. He called Wednesday to let Sara know he’d be flying into an airport about 2 1/2 hours away. There were two other airports much closer to where Sara lived and she told Randy that. But since the reservations were already set he continued on with his plan. During this conversation he asked if she could meet him at the Airport. Sara was baffled that he would expect her to drive that far to pick him up. She stuttered .. oh, uh, No, .. I have to work – I can’t ask off at this point. During the calls following his departure Randy continued to suggest Sara try to get off and meet him. Sara was not looking forward to this visit – but she tried to remain open minded ... afterall, there was a lot she liked about Randy.

When Randy arrived at the airport he rented a car and drove himself to her house. In preparation for Randy’s coming, Sara had decided to ask her grown daughter and children to join them and spend the night. It was a precautionary measure she felt she needed to put in place in case Randy didn't book a motel again (which of course he did not.)

Randy arrived at 6:30pm. Sara went to the door when he knocked. She opened it with a smile and he greeted her with a hug and a kiss on the cheek. She introduced him to her daughter Jill and her grandchildren ... Randy was cordial ... but not warm she noted. Sara had prepared a very nice meal that evening and as they sat around the table talking, laughing and eating, Sara was debating about taking another portion. She made one of those exaggerated proclamations, saying “I probably shouldn’t take seconds; I feel like I’ve gained 50 lbs.” Randy spoke up and stated very matter of fact “Yes, I can see that.” …. Sara froze in place and stared at him in disbelief… “Are you saying it looks like I’ve gained 50 lbs in 3 weeks?” she asked. Randy answered, “Yes, but it doesn’t bother me.. “ Sara responded, “Well, it bothers me!”

The next day Sara took Randy to a local beach. They sat on a blanket on the sand and enjoyed the sun. They engaged in some light conversation as Sara relished the warmth of the sand on her feet. After a while Randy suggested they go grab a bite to eat. He got up, offered his hand, and with a chessy cat grin said, “How about YOU get up so we can clear a spot for ALL of these people.” Sara stared at him in shock … Suddenly she pictured herself as a grossly huge woman sporting an itsy bitsy teeny weeny bikini. Talk about adding insult to injury … this guy should have written the book. “That was very rude Randy.” Sara stated.  Randy chided her saying “Sara, can’t you take a joke?” Sara was indignant! “That was not funny – it was rude” she insisted. Randy tried again “Haven’t you ever heard of sarcasm?” Sara ended the conversation by saying “Yes, and I hate it!”

As they walked in silence toward the diner Randy suddenly grinned toward Sara and spoke lightly, “If I buy the lunch, can you leave a tip?” Sara just shook her head numbly and said, “I don’t even have my purse with me.” By this time Sara felt disgusted and knew she could not tolerate much more.

After lunch Randy relaxed and seemed to be pleasant. “How about we go out for a romantic dinner tonight?” Randy suggested. Sara thought he was making an effort to make up for his misconduct… but then he added, “Something not too expensive.” “What is with this guy?,” thought Sara … “I understood him to be financially stable.” She thought about the local restaurants and then suggested a reasonable but quaint local establishment. At dinner time they drove to Toni’s Temptations. Before being seated, Randy asked to see a menu. After looking it over he furrowed his eyebrows and said to Sara, “This is kind of pricey, is there somewhere else we could go?” Now she was shocked and a bit angry too because number one Toni’s is NOT what most would consider pricey and number two … the nerve of this man! Sara, feeling indignant and confused, led him out the door. They ended up, of all the places, at a Chinese buffet… ahhhhh the romance to be had at the buffet … not THAT night … and Sara was thinking…. Not EVER!

It was the night before Randy was to leave.  Sara made sure that her daughter Jill was at home. After dinner Jill and her boyfriend joined them for a movie. Just before the movie, out of the blue, Randy looked at Jill quizzically and said … "with a nose that big … how do people see around you?"  Jill’s lips struggled into a nervous smile … but she said nothing. Later she asked in a distressed voice … “Mom, Is my nose really big?” It is NOT big and in fact Jill’s nose is very petite, just like Sara's.  Sara could not believe the audacity of this man thinking he could get away with insulting Jill.

Sara made it through the movie as her mind raced and her emotions ran rampant. After the movie Sara excused herself by saying she needed to lay down with her granddaughter Amy. She told Randy that she might not come back out ... "Sometimes it takes Amy awhile to fall asleep." As she laid there she began to feel guilty. Here this man came all this way just to see me .... so the dialogue went on and on in her mind until she forced herself to get up. When she came out of her room she found Randy sitting at his computer again. She told him she was getting herself a drink of water and asked if there was anything he needed. He looked at her and raised his eyebrows.. his lips curled mischievously as he asked, what do you have in mind Sara? Sara was thinking .. How about murder Dumbo!, but instead replied, “A glass of soda, water or milk?

With one last day to endure, Sara had decided to take Randy to her Church. Before they left the house Sara spotted Randy’s fly was open. She kept hoping he would see it and zip it up ...… but … it was not to be. Although she did not want to tell him, she decided the alternative … taking a strange man to church with his pants unzipped … was worse. As she casually walked out to the car, she whispered quietly, “Your zipper is undone.” Randy reached to zip, smiled and said, “I can see where you’ve been looking.” Poor Sara was mortified. He must have noticed the shocked expression and continued, "It’s not bad for you to look there.” That did it! Sara had her full of his ignorance and rude remarks.  She replied, “That was totally inappropriate!” She was really mad!

During the Church service Randy seemed disconnected and even left the sanctuary for a time. After the service, to make conversation, Sara asked what he thought of her Pastor’s Sermon. Randy answered; “It was like shaving with a banana.” Although she didn’t have a clue what he meant … she was sure it was yet another insult".

That day Randy finally left for his home acting absolutely clueless as to the chaos he had created during his stay. As he said his goodbyes he appeared totally happy and contented … except for a little complaint about having no time alone with Sara. All Sara could think was “Thank God he's leaving and this is nightmare is OVER!”

After Randy arrived back home, emails started to flood Sara’s box. Sara was working on formulating a letter of her own. She wrote to Randy and tried her best to communicate the injury and insults of his visit. She read the letter to me and I was very impressed with how clearly and kindly she communicated. At the end of her letter it was very clear that the relationship was over.

Randy was very distressed and seemed confused. He could not understand why she took him wrong … he continued with more and more emails. In one email he told her that it must have been his comment about the Church .. He went on to say he was just going to have to leave it to God to show her... the arrogance of this man was unbelievable! He tried pleading for another chance. He told her he really didn’t care about her weight (she’s not fat) and claimed he was only teasing her. He explained that she needed to lighten up and not be so sensitive. UGH! Sara had tried to be clear … but to no avail. He also asked for his picture back but continued to try to woo her. As has been established in Part One; once Sara makes up her mind .. that’s it ... no turning back .. it was done and over.

That was THE END and with that … another mystified potential lover was checked off the list and Sara was off to create her next dating story.