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Funny Internet Dating - Rich and Rude Randy

Updated on September 13, 2017
Mekenzie profile image

My friend Sara has the craziest dates ever! These funny internet stories are meant to entertain as well as warn those on the dating quest.

Internet Dating


Dating Story

Welcome back to Sara's Internet Dating Stories. Sara is a charming, intelligent woman who has experienced some of the craziest situations through meeting men on dating sites.

So far, I have written three of Sara's hilarious mishaps in the dating world. The first story in the dating series is about a hopeful suitor named Todd. To read this engaging short story go to Too Much Too Soon Todd. If only Todd had slowed down and allowed Sara time to get to know him the outcome might have been so different.

This is the second story of a completely different suitor. Sara and I have named him Rich and Rude Randy. The details of this story are bit long, so it is divided into two parts. The second half of the story will be found at the end of this article.

Finally, the third dating disaster finds us waiting with Sara to meet a charmer we have deemed Roaming Richard. You will be pulled into Sara's emotions as she anxiously awaits her date with this mystery man.

Remember as you read these short stories that all three are true. Sara and I are excited to share her adventures. I hope you are thoroughly entertained and enjoy reading about the crazy dates my dear friend has endured and can even laugh about today.

Could he be the One?

Are you my Happily Ever After?
Are you my Happily Ever After? | Source

Rich and Rude Randy

Today's 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. Everything I write about Sara and 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 what happened. The scenario's played out just as I have written.

Dear Sara, so filled with trust and hope. She was surprised, once again, as the lovely curtain of her dream was pulled back to expose an ugly reality in the face of another unfit suitor.

She wonders where these guys come from. Before her encounter with Rich and Rude Randy, she had never known a man could be so blind and oblivious to his own horrendous character flaws.

Sara gets so exasperated at herself as she remembers the many red flags. She wonders why she didn't cut things off sooner.

Fact Checking with Google

Could he be the one?
Could he be the one? | Source

From a Distance

The conversations between Sara and Randy began as light and comfortable. 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 was financially secure. He also professed to be a Christian as was Sara.

Out of curiosity and as a precautionary measure Sara googled his name, his business, and his house address. His house was large and exceptionally beautiful. She could see an outdoor swimming pool when she looked on Google's bird's eye view. "Yes!" Sara exclaimed out-loud, "This man checks out to be who he says he is." Feeling fairly satisfied with what she found on the internet she continued to communicate.

Over a period of months, they began to know each other better. Randy sent her a picture of himself. There was no doubt that he was handsome and from a distance, Sara began to grow very fond of Randy.

He listened attentively and was very caring. When Sara was having trouble with her car, Randy offered to take care of it. He told her to rent a car stating he would pay for it. Sara declined but was touched by the gesture. Over time she began to see glimpses into his heart and it was good.

The day came when Randy asked her if he could fly in and take her on a date. Sara contemplated the pros and cons of going on a blind date with someone who lived so far away from all of her friends and family. Though a short conflict waged war in her brain, curiosity won out. After only a moment's pause, she agreed.

In preparation for their first date and because Randy was traveling to meet her Sara gathered the names and numbers of some local hotels. She discussed the accommodations with Randy and sent the information to him.

Sara gave great thought to the best place to meet for a first date. She chose a fine dining restaurant that was elegant and romantic.

Her heart began to fill with hope and anticipation for the weekend when she would meet Randy face to face. She hoped this would be the first of many dates and then, 'who knows' she thought as her smile turned whimsical and her eyes took on that far away look.

First Date

She sprayed a 'safe,' sweet, light fragrance under her neck rather than her favorite perfume which held the power of allurement.
She sprayed a 'safe,' sweet, light fragrance under her neck rather than her favorite perfume which held the power of allurement. | Source

Preparation for the First Date

As Sara was getting ready to meet Randy at the restaurant she caught her reflection in the mirror and smiled happily.

She recalled some of the conversations she had with Randy. He had made it clear that he cared for her. Sara wanted to look her best. She thought about every detail from her hair to her clothing and makeup. She decided to wear a lovely light rose sweater which complemented her fair skin. Sara does not own or wear much jewelry but what she has is quality and makes a statement. She chose her diamond pendant necklace and earrings.

As she carefully piled her curls on top of her head, pinning them in place, she pondered many thoughts about how the evening might go. Before heading out the door she sprayed a 'safe,' sweet, light fragrance under her neck rather than her favorite perfume which held the power of allurement.

Richard Arrives
Richard Arrives | Source

Meeting Richard

Pulling into the restaurant she searched the parking lot. She was five minutes early and pretty sure she had reached the restaurant before Randy. Sitting in the dark anticipating his arrival she began to feel 'butterfly's' in her stomach ... a mixture of excitement and anxiety. Just before he pulled into the lot Sara began to question and scold herself. "This is a crazy idea, why did I say yes? What have I done?"

As she kept her eyes glued on the entrance to the restaurant she spotted a Red sports car pulling in. Sara held her breath and watched speculatively to see if it was her date. The car pulled into a spot across the lot from Sara. As she watched ... the door of the car opened and Randy stepped out.

His eyes scanned the parking lot until they rested on Sara who was still sitting in her car. Sara's beautiful smile welcomed him. Randy was handsome, and as he walked toward her he shined with confidence!

Next thing she knew she was talking to herself, "Okay Sara, it's time to step out of the car, you can do this." Stepping out of the car she caught his eyes and read kindness and approval. Sara took a quick assessment as he approached, "My, he is one classy man!" Sara felt her heart stop but then realized it had only skipped a beat.

He was quite tall with thick dark hair that curled in the back and around his ears. He was so very attractive in his khakis and rich brown twill sweater. He wore good ole prep loafers on his feet …Inwardly Sara's heart was singing, “Just my kind of guy!”

As Randy drew nearer Sara noted how his eyes smiled right along with his mouth. He greeted her with a gentle hug and a kiss on the cheek, “So, we finally meet Miss Sara,” Randy said as he studied her. “You are really much more beautiful than your picture reveals.” “Why thank you, Randy,” Sara replied, feeling a sudden shyness.

As they walked toward the restaurant, Sara once again observed Randy’s confidence and self-assured stride. He opened the door as he placed his hand on the small of her back.

Romantic Dinner

Dinner for two
Dinner for two | Source

Romantic Dinner

When the waitress approached them Randy gave her his name for the reservation. The waitress smiled as she waved and said with a bright smile, "Right this way, table for two."

As they walked to their table, Sara looked around feeling smugly satisfied with her decision to meet at this restaurant. The atmosphere was inviting and romantic with candles glowing in the dimly lit room. Delicate flowers adorned each table. Soft amorous music filled the air; "Perfect!" she mused. Randy ordered their dinner and took care to see that Sara was comfortable and received everything she wanted that evening.

Randy ordered their dinner and took care to see that Sara was comfortable and received everything she wanted that evening.

As the evening progressed Sara began to feel relaxed and to enjoy the attentions of this man. This first date was going very well. Randy proved to be a comfortable man who smiled easily and engaged her with his eyes.

The conversation was stimulating and Sara felt more convinced that Randy was a solid and dependable man. His hands were large well groomed; His facial features were strong and ruggedly handsome. When Randy smiled there were well-worn smile lines creasing his cheeks and at the corners of his eyes ... endearing himself to Sara.

As Randy talked, Sara's thoughts drifted to appreciation for the huge step Randy had taken just to meet her. She thought about the small amount of time they would have together. Two days seemed very short as she sat looking into Randy's beautiful and kind eyes.

Finishing up a decadent chocolate dessert Sara asked Randy where he was staying. Randy replied, “Oh I need to find a place.” Sara was taken back and felt discomfort trickling through her veins as she wondered what he meant. Hadn't he made hotel arrangements?

Motel Full
Motel Full | Source

No Room

After dinner Randy invited Sara to ride him so she could direct him to the best local hotels. Pulling into the Holiday Inn Sara was furtively hoping they would have a room. As they walked through the door and into the lobby Randy whistled as though he had not a care in the world. He approached the clerk and asked for a room. With a look of regret the hotel clerk said, "I'm sorry sir, there is no room, the hotel is booked full."

It was a tourist weekend and Sara had feared this would happen. The hotel clerk advised them that all of the local hotels were full. Sara's heart fell. "What in the world will he do now? Oh, she fumed inwardly, I knew this was a bad idea!" Richard shrugged his shoulders as he gave a sheepish smile towards Sara. Touching her arm he directed her back to his car.

As they walked quickly and quietly to the car Sara felt anxious wondering what to do next. She did not have to wonder long because Randy seemed to have a plan. He began “Ya know I threw a blanket and small pillow in when I left; I can just sleep in the car in your driveway if that's okay.” Sara was stunned by his words and though she wanted to respond with a firm No way!, she found she could not find her voice. It was a ludicrous idea for him to sleep in her driveway. Sara felt she had no choice but to volunteer a room at her house. Randy readily accepted her offer.

My Home, My Safe Place
My Home, My Safe Place | Source

Welcome to My Home

As Randy drove Sara to her car she was fretting, "What have I gotten myself into!" Thoughts began racing through her mind, "Am I crazy?" She didn't even really know this man ... but what choice did she have. When they arrived at the restaurant Sara hopped out, without a word, and hurried for her car. Soon they were pulling up in her driveway. Sara took a deep breath as she stood waiting for him to join her. Opening the door she welcomed him inside by saying, “Come on in."

Randy looked around the room approvingly as he motioned toward the couch with a question in his eyes. "Sure," Sara responded, "Have a seat, would you like a glass of iced tea?" she asked. "That sounds great, thank you Sara."Randy answered with a grateful smile. After pouring the drinks she rounded the corner to the living room catching a glimpse at Randy's face covered with contentment. She smiled and felt herself relaxing in his presence but then she quickly warned herself not to let her guard down.

Following a short discussion about which movie to watch Sara slipped the disk in the player, turned on the television and sat down beside him. Randy had agreed on a Chick Flick, Sara liked that idea. As they watched Sara felt the tension leave her body. It was a movie Sara had seen before and as she got caught up in the story it took her mind off the predicament she was in.

When the movie came to an end Sara's anxiety reappeared. She got up quickly and told Randy she would be back in a minute. Running from the hall closet to the bathroom she grabbed her comforter, linens and a set of towels and then walked back to the living room. She asked Randy if he would move to the chair so she could make up his bed. "Sure," said Randy, "but let me help you with that." Randy took the towels and comforter and put them on the chair. He helped Sara put the linens on the couch seeming as though he did this every day.

After the linens were in place she excused herself saying, "Goodnight Randy, I'll see you in the morning." She hurried to her room and shut the door quietly. Standing against the door, she could feel her heart beating heavily. She once again chastised herself for the stupid decision she had made to invite a stranger into her house. "I must be mad!" She pulled her little antique chair under the doorknob and jimmied it until it was tight and snug. She fell into bed as thoughts and visions of murderers, rapists and thieves danced through her head.

After a restless night she woke up early the next morning. As she lay in her bed listening for movement, she felt utterly and completely exhausted. Struggling to get out of bed and on to her feet she reached for her pink robe and fuzzy slippers. Quietly she opened the door while smoothing her hair in place. She peeked out and saw that Randy was awake and working on his computer. His mouth broke into a wide smile when he spotted Sara standing there in her morning fare. “Good Morning Sunshine.” He said cheerfully. Sara couldn’t help but smile back. “Good Morning, did you sleep well?”

The better part of that day was spent walking the main street. Sara gave Randy a quick tour of the quaint and interesting shops that adorned the town. As they leisurely strolled and chatted she felt herself relaxing and enjoying his company. Later that day, when Randy left for home, Sara felt relief but she also noted a tug at her heart. They had shared some good conversations sprinkled with plenty of laughter. In reflection Sara was pleased that he turned out to be a good guy after-all.


If I was Sara

See results

Rich and Rude Randy Part 2

Follow along as we look in on what happens when Randy invites himself to Sara's for a second date.

Sara is still hopeful and giving Randy the benefit of the doubt. What happens when she opens the door to Randy's efforts to win her over again?


Online Dating Tips

  • Take your time to get to know a person from a distance. The more time the more comfortable you both will be. The real person will come out as time goes by.
  • Take the personality and compatibility tests - they are scientific. It won't take you a year to learn whether or not you are compatible.
  • Post a picture with a profile. This allows suiters to get an idea of what you look like... takes some of the risk away.
  • Write a detailed profile ... it usually lists Interests, habits, smoking, etc. ... some even post income.
  • Don't be naïve. Caution must always be at the forefront. Meeting at a local restaurant - double date for the first meeting - checking into references. .... Do your homework
  • Listen to your gut. If you have any flags going up, pay attention.


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    • Mekenzie profile imageAUTHOR

      Susan Ream 

      4 years ago from Michigan

      You've got that right Peg! Thanks for stopping by for a read and a thought. Have a GREAT day!!


    • PegCole17 profile image

      Peg Cole 

      4 years ago from Northeast of Dallas, Texas

      This guy seems like a master manipulator with a convenient spell of forgetfulness about making hotel accommodations. He made some serious assumptions for a first date.

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      7 years ago from Michigan

      Efficient, yes worse than the worst. Downright scary! My poor sweet friend Sara still searches for her true love. I'm hoping someone worthy of her trust finds her.


    • Efficient Admin profile image

      Michelle Dee 

      7 years ago from Charlotte, NC

      Oh my gosh, this guy is the worst!!!!!

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      9 years ago from Michigan

      aefrancisco, I'm so glad you enjoyed Sara's story. There is actually a part 1 and 3 too. If you liked this one, you'll be amazed at the crazy situations she found herself in .. in the other two stories. Thanks for stopping by and leaving your laughter.


    • aefrancisco profile image


      9 years ago from somewhere down the road

      hehehe ... this is great :)

      love it ...

      can't help but smile and

      it reminds me of something - which i almost forgot...

      thanks for the wonderful hub :)

      more please :)

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      9 years ago from Michigan

      Janny, I have to tell ya that Sara hasn't dated for a while after this latest let down. She does have a tremendous sense of humor though and we laugh about it alot. LoL

    • JannyC profile image


      9 years ago

      Wow yeah I consider myself lucky now. Maybe that is why I dont date much either. Hahaha

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      So Micky Dee are you telling me that you have some stories you could tell? :-)

    • Micky Dee profile image

      Micky Dee 

      10 years ago

      Hi, I'm Randy. No, that's my name. I'm rich and just drove my yacht into town. Can I sleep in your driveway? Thank you Mekenzie. I'm sure these folks are real. Unfortunately it gets "realer" than this!

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      awe, thanks Mike. I just went through and did a reread. I found some mistakes and realized a better choice of words (with some scenario's) would make the scene clearer. I tend to publish too quickly and it looks like I did that with this hub... UGH!

    • Mike Lickteig profile image

      Mike Lickteig 

      10 years ago from Lawrence KS USA

      I agree with Ghost Whisper, these dating stories are addictive?

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      I actually have a part 3 I am working on. I keep getting other topics popping into my head and they have been taking priority. Thanks for the encouragement - I'll get to it. :)

    • profile image


      10 years ago

      Funny, funny, funny, and sad for Sarah. Great writing, I look forward to part 3. Toni's Temptations, instead of a restaurant, it sounds like my former life. But, I resisted of course. Keep em' coming!

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      Richard, I know .. eharmony has been a good source but costly ... she did find some very nice men through online dating services but alas ... situations like he lived too far away or in one case he was 4" shorter than she, even though the profile said otherwise ... one had an issue with commitment or the attraction did not go both ways. Sara, keeps running into walls - one way or the other - but she doesn't give up, bless her heart. It gets harder, as you get older, to find someone to date unless you frequent bars and such which Sara does not. I remember my high school and college days when there were many potential suitors to go around ... I found my true love while attending college.

    • livewithrichard profile image

      Richard Bivins 

      10 years ago from Charleston, SC

      LOL another good story. I think your friend Sara needs to pick a better online dating service or go out and meet some real people.

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      Thank you antonrosa - I appreciate your stopping by and I'm glad it made you laugh.

    • antonrosa profile image


      10 years ago from USA

      Haha, how interesting. A good read!.

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      PastorAndrew, Isn't that a riot! Sara and I get the same way when we talk about Randy. We laugh til the tears roll. He was something else. Ya never know what kind of character might walk in on one of your sermons do you? If you someday find a stranger visiting and his name is Randy; ask if he knows Sara. If he does ... take no stock in what he says. Believe me ... his vote doesn't count! :0)

    • PastorAndrew profile image

      Andrew Grosjean 

      10 years ago from Detroit

      Shaving with a Banana! That is the funniest thing I have read on HubPages since coming here. That was hillarious. I hope people do not find my preaching like trying to shave with a banana! I can't stop laughing!!!

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      Hello SL, so you found your love through using the internet - how cool is that! I have some other friends who have also been very successful with internet dating. I think the internet is especially helpful for those of us past our 20's. It gets more difficult to find single and eligible people to date. I think the internet is a great tool as long great caution is used... Thanks for your kind words.. I'm so glad that in your marriage the embers of your love for each other continue to glow warmly - That's a GREAT testimony.... Blessings to you and your sweetheart

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      rmcrayne, I am new to HubMob. I wrote Princessa last night because I wrote the Hub first and published it; forgetting that I was supposed to go through the steps. Princessa said that I could write about part 2 in the forumn and explain what happened (since I am new) but the process is automatic and couldn't be changed. She said I could either start over - which would take hours - or post a link. I'm going to put a link between Part I and Part II. Thanks for Stopping by!

    • SL Perrin profile image

      SL Perrin 

      10 years ago from South Carolina

      A good piece that shows the tough parts of internet dates. For me the internet helped in my finding a gal that was great to chat with. Most folks seek to have pix of the ones they chat with but in my case i did not care nor did she. She had many personal questions that she was marking off as we chatted to ensure that I met her standards as a Christian. Well Mekenzie we have been married now for 10 years and we still feel the same now towards each other as we did on the wedding day. I love the way you show his arrogance and her patient kindness with the whole situation.

    • rmcrayne profile image


      10 years ago from San Antonio Texas

      This part II is not showing in the HubMob RSS. Did you start it from Princessa's forum thread Romance HubMob link?

    • Mekenzie profile imageAUTHOR

      Susan Ream 

      10 years ago from Michigan

      Me too - kicked him right to the curb! Sara is very kind and reflective - it's hard for her to kick anyone... LOL. Sara has a great sense of humor. We we have laughed til the tears roll down our faces when we remember some of the hilarious and crazy situations she's been in. I sure hope and pray she finds a good man who treasures her.. She is special. I am so glad that you enjoyed the hub ... I value your opinion. Writing in a story format is not my normal style so I really had to work on this writing project. Thanks for your comments and for reading it dear girl! Blessings

    • AEvans profile image


      10 years ago from SomeWhere Out There

      Oh Goodness!! Randy was something I would have kicked him to the curb but Sara did the right thing and had her kids with her when he came the second time around. I love the story! :)


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