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Going Fishing with 50-Year-Old Bait

Will she catch anything?

It's time. Let's do this! I have not dated since ... well ... dinosaurs roamed the earth. Or at least it feels that way. However, my son is grown and living his life, so now I guess it is "my time." Sitting at my desk, I stare at the dating site, feeling like I am entering the twilight zone.

The first thing it wants is me to enter a screen name. Hmmm. What should I put here? Everyone always calls me Penny, but I think I will use my birth name, Penelope. That’s a fun name, right? A name a man will remember. So, I type “Penelope” as my screen name. 

Next - desired age. Well, what do I want here? Younger would be nice since studies show the women typically live longer than men. I don’t want to get my perfect man and then have him die in a few years. But, a little older might be nice. His kids will probably be grown and he might be closer to retirement and having more free time for me. I am fifty, so maybe forty-five to fifty-five is my range. Yep, that is a good range; let’s go with that.

Last - upload a profile pic. Okay, I need to think about this one. I rummage through all my pics on my phone and my choices are very limited. Selfie-queen, I am not! Oh, here’s a good one. I am wearing a black halter top which shows off my tanned shoulders and slims my too-big-for-my-body breasts. But wait, am I thinking this through? I probably don’t look this good in person. What if he loves me in this pic and we meet in person and he asks why my grandma showed up instead of the woman in the picture? Maybe I should use the plain jane pic with no makeup. Better he sees this now, right? Then, he will be pleasantly surprised in person. But, if he doesn’t like my profile pic, I have no chance to prove myself to him in person. Oh, crap! This is hard! The profile pic is so important. I mean, will the guys even read my profile? Won’t most just pick or nix me based on my picture? Ugh

I decide on a picture somewhere in between. I am wearing some makeup, but not wearing my best looking outfit. Picture uploading. Now, I move on to the written part of this application process. It is an application. I am applying for the position of girlfriend or hopefully future wife of an amazing man. This is my time. While I was raising my amazing son, and choosing not to date, which I do not regret, it stung to see all the social media pictures of loving couples on Valentine’s Day. It stung to see all the couples holding hands in the mall and sneaking sweet kisses in the movie theatres. It stung. But, now it's my time. And I will find the best man of all! I will have the romantic pics to post. People will stare at me and my handsome, perfect man with envy as we walk hand-in-hand in public. And, I won’t settle. Mr. Perfect is out there and I will find him!

I vomit out my detailed list of requirements to date me. It is quite an extensive list. Oh, and I need the deal breakers too. I don’t want to waste any time with the wrong guy, so just get all the crap I don’t like out in the open. Done. Submit profile - click!. Yay! Let the perfect man come find me!

An hour passes with me staring at my screen, and no messages. Not one message from one man. A watched pot never boils, so I decide to log out and be pleasantly surprised tomorrow.

Next day...

Crap! Not one message. Disbelief fills me. I spend a few minutes in self-pity and then I pull up my big-girl panties and decide to take matters into my own hands. First, my profile pic must be wrong. I decide to go back to the picture with me wearing the black halter top. I look the youngest in this pic. In the other, you could see more of the wrinkles around my eyes. Then, I click on "Search". I will make the first move, I guess.

The first thing that stops my heart is the screen names: SexyandLooking, LastFirstKiss, MrBlueEyes. What? Where are their real names? Oh … my … gosh. Not a single man has used his real name. I stupidly put my real name as my screen name. Will an undesirable man be able to find me now? I had not thought about all the dangers of online dating until this moment. My mind floods with visions of serial killers, stalkers, and ax murderers. I frantically go to my profile to change my screen name. I cannot. It is apparently part of your profile key that I cannot change. Ok. Don’t panic, Penny. It is just your first name. Just breathe. Remember the task at hand – searching for Mr. Right.

Then, I see him - the man who brings on my second cardiac arrest – ToeLicker. A horrid looking creature ... I mean man ... sitting shirtless on his bed, looking straight at me, with his tongue out. How scary. What a scary, scary man. Then I spy MagicoPantalones. Now, I don’t know Spanish, but I know what this screen name is referring to. I pull up his profile and he has semi-naked pics with a smile attached that screams he wants to do very bad things to me. Oh my gosh. Is this what awaits me? These are not the knights in shining armor my mind envisioned. Calm down, Penny. Then, it happens. I get a message. Phew! My luck is changing. I race to my inbox and it is from ToeLicker. Crap and yuk! I feel like I will catch a disease just hitting "Read". He says, “I saw you viewing me. You are beautiful and I bet you have even more beautiful feet.”

Delete. Delete. Delete. I cannot press the delete button fast enough. So, they can tell when I view them. That’s just great – not! But, wait. I can see them view me too. Scanning my screen, I find the “View” button. I hit it. My heart excitedly races as I see all my views. One after another, I scroll through all the men who viewed me. Then, my excitement halts as a realization hit me. All these men viewed me … and then passed on me. I sink back in my chair in utter disappointment. Was it what I said in my profile? Was it my picture? What is wrong with me? In frustration, I close my laptop and go find the nearest ice cream store. Chocolate ice cream will do nicely.

Next day...

I wake up with a new plan. I am going to find five wonderful men and send them a message. This is 2020, the age of strong women, and I will take online dating into my own hands.

Let’s see who the lucky men will be. Scanning. Scanning. Scanning. One thing that is catching my attention is their age ranges. What is going on? The men in my range have selected the desired range of ten to fifteen years younger. I can’t find one man near fifty who selected the desired age range with me in it. Oh boy. Am I too old to attract a mate? Ding. My computer just signals me that I have a message. Holding my breath, I hit the message button. There he is - the man who is attracted to me is seventy years old. Ugh. I struggle with how to respond. I don’t want to hurt anyone’s feelings. Should I just ignore his message? No, my conscious tells me to thank him and then let him down easily. I sweetly thank him for my message and tell him I am sorry but I am looking for a man closer to my own age. A second later, he responds. It isn’t good. I didn’t know until now that there was a middle finger emoji. He adds to his one-finger wave a comment saying that it is my loss because he is a millionaire and has sex with his girlfriends five times a week. Wow! I am offended on so many levels. I decide to just ignore the undesirables from here on out.

By some miracle, I find five attractive men with normal profiles. My list of requirements has gone by the wayside. I am just going for close to normal right now. I send my messages bravely expressing my interest in these five lucky men. I sit and wait. And wait. And wait. One by one I see them view me. Then, I wait. And wait. And wait. What the hell? Another profile picture change is needed. I find one showing some cleavage and apply a filter to hide some more wrinkles. Yes, this is cheating. No, I don’t care.

My computer dings. Guess what?  A seemingly normal man responds. And so it begins.

Three days later...

Date night! In my head, I have us married. He checks all my boxes. We have had the easiest texting conversations over the last three days. We had lots of "lol"s together. We shared secrets. We shared similar dreams for the future. All that is left before the wedding is for us to meet in person.

I am shaking with anticipation as I drive up to the restaurant. Checking myself one last time in the mirror, I get out of the car. The face from his pictures walks toward me but not the body. I am 5’4. And I find myself looking at his forehead in person. His profile said 5’10. With 7-inch heels on, maybe. Gulp.

Then, he opens his mouth and Kermit the Frog comes out. A deep, soothing voice had been in my head. Another gulp, followed by light-headedness hits me.

Don’t be so shallow, Penny! So what if he’s a little shorter than you. So what if his voice isn’t James Earl Jones. He could still be the one.

We hug and I feel him rest his head on my shoulder for just a second. This doesn’t endear him to me.

“You look great! Better than your pictures even,” he says smiling.

I am unable to speak yet and just smile back.

Once seated, he asks if I would like a drink. Yes! Yes! Yes!

“Wine, please,” I say. Definitely need some wine!

Have I told you I have not had a drop of alcohol for fifteen years, while I was in my "be-a-good-role-model" stage? A quick tip: if you have not drunk alcohol in a long time, a first date is probably not a good time to try it again.

I need to give this date a chance. Our texting had been amazing. We have so much in common it seems. We both love to travel. I will explore that topic with him.

“So, where is the last place you traveled?” I ask, optimistically.

“Oh, I went with some buddies to a singles-only resort. Titties everywhere. But, after the first day, I got used to it and they didn’t affect me as much. I was like, ‘Oh, saw those titties yesterday, no biggie’.”

Mouth drops open. Did he just use the word “Titties.” He used it not once but twice. That word has always made me cringe – ever since high school. I drink half my glass of wine in one gulp.

“I would love to go to a couples resort with you sometime,” he says. Then, he leans in to whisper, “Your titties are amazing by the way.”

The rest of my wine is gulped down.

“May I have another glass of wine, please,” I ask the waiter.

“Do you like wine? You are drinking it kind of fast, aren’t you?” he asks.

“Yes, the wine is great,” I respond, willing the waiter to hurry.

More chit-chat follows with crass words pouring out his mouth that makes me cringe. The second glass of wine arrives and is gulped down my eager throat. Then, I have to pee – of course.

“I need to use the restroom,” I say politely to my 5’3, frog-voiced, titty-talking date.

I stand up from my chair and swoon and immediately fall back into my chair. Oh crap! My head spins. I am drunk. I couldn’t tell until I stood up. My hands rush to hold up my head.

“Hey, are you alright?” he says in surprise.

“No. We need to leave now, while I am still able to walk to the car.”

“Really? Are you serious?”


I throw cash at him and in one rush of movement, fling myself towards the door and get to the car before collapsing against the door in dizziness. Within a few moments, he is beside me, taking my keys, and opening the passenger side of the door.

“Get in. We will just sit in the car and let you rest,” Kermit says kindly.

I more or less fall into the seat and lean my head back. Oh no, bad idea. I lean my head forward, supporting it with my hands resting on my knees. I hear the driver door open and see him slide in the car beside me.

“Are you ok?” he says, shaking his head in disbelief.

“No, I am so sorry. I feel so drunk and can’t move.”

“Ummm. It’s Ok. We can just sit here awhile. Ummm. I think you might have a problem with alcohol, Penelope.”

I burst out laughing. Not sure even why.

“I have not had a drop of alcohol in fifteen years. I think I just am not used to it and drank my wine too fast.”

“Well, we need to get you something to eat. Fazolis is right next door. Let me walk over and get you some breadsticks,” he says sweetly.

“No. No. I don’t do carbs.”

“You are doing carbs tonight, Penelope!” he says, with his patience gone. And with that, he leaves to buy his drunk date some breadsticks.

He returns and stuffs breadsticks into my mouth while I lay my head back against the headrest. I hear lots of giggling, I assume coming from me. The next thing I know I am opening my eyes and it is dark outside. Soft music is playing in the car and he is on his phone beside me texting.

“Hey, you are awake? How do you feel now?” he says, looking over at me.

“Oh, pretty good,” I say groggily, rubbing my head. “Have you been sitting here all this time? What time is it?”

“Well, you have been asleep for about an hour and a half. I figure most of the wine has left your system by now. Ummm, Penelope, I really do think you might reconsider drinking on dates from now on.”

You think?

Next day...

I don’t believe it. Kermit the Frog sends me a message saying he wants to see me again. What the … what? He is more messed up than me if he thinks the hot mess he took out last night is relationship material. I am so embarrassed by my behavior. Also, the realization of the danger of getting drunk with a stranger sinks in. He could have taken advantage of me in my drunken state ... I mean, if he were bigger. I could probably have still won in a wrestling match with him. What was I thinking? Have I lost my mind?

I stare at my screen of men, hoping Mr. Perfect jumps out at me. Then, it hits me. Like a ton of bricks, it hits me. From start until now, I have been going about this the wrong way. You can’t truly know if someone is right for you based on a picture and a few words. You need real-life in-person interactions. Yes, you can find your start here … maybe. For some, this may work. A lot of luck would have to be involved though.

I reread a few profiles. I am not the only delusional one here. Many have a list no real woman could ever meet. Most of us have been divorced. We had a failed relationship, and think the perfect person is up next. There is no perfect person though. If you are fifty years old, you can bet you have some baggage. We have probably learned some things in our failed relationships though. If we are smart, we see our role in them. Many, like me, think we know exactly what we need. We don’t. You can’t possibly know for sure until you meet face-to-face with someone and see your in-person reactions to one another. You can make contact through a text, but can’t know for sure if it is right until you meet in person. I need to spend this evening seriously thinking about my future with online dating. Mint Chocolate Chip ice cream helps me think.

Week later...

After gaining five pounds this week eating ice cream, I decide, for now, to get off this roller coaster. I never in my wildest dreams thought it would be this hard to date again at fifty. Naively, I envisioned Mr. Perfect right there waiting for me. He would take one look at my profile picture and recognize me as his match made in Heaven. We would text a little, meet, and as soon as we laid eyes on each, our hearts would melt. The conversation would easily flow. It would be like we had known each other our whole lives. We would have our last "first kiss". Dating would quickly turn into a committed relationship. A committed relationship would evolve into marriage. And I, Penny, would have my happily ever after. I figured I was still young enough to see a twenty-year anniversary.

Nope. Didn’t happen. I am pretty sure I cycled through every imaginable emotion within the last week.

Cancel subscription.

Delete account.

Food is my answer … well, mostly ice cream … but, a few fruits and veggies to help me look normal to the grocery cashier. Driving to the grocery store, I feel melancholy. I can’t give up yet though. Love is too amazing to give up on. As I peruse the fruit section, I see him - a tall, ruggedly handsome man is carefully squeezing the melons. I swear this is happening. I look no more than a few seconds before his eyes look up and catch me staring. I dart my eyes away. My mind forces them to sneak a peek again and then his eyes dart away. We do this dance for a few minutes before he drops a melon and it rolls towards me. I pick it up and slowly walk it over to him.

“Here, you dropped this,” I say quietly.

His strong hands graze mine as he takes the melon from my lightly shaking hands.

“Thank you, beautiful,” he says smiling.

Beautiful! He called me beautiful. Squeal! Squeal! Squeal!

“My name is Penny,” I bravely say to him, trying to remain calm.

His deep voice replies, “Hello, beautiful Penny, I am Rick.”

And this 50-year-old woman leaves the grocery store with more than I came in with – a date with a nice man.



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