Jessie Cali
- Jun 1, 2020
- 9 min read

Dating Sucks: Let's Talk About It

Updated: Mar 24, 2023

First things first, despite the title, this blog post is meant to encourage people who are dating. This was written in an effort to make sure fellow daters are in it for the right reasons and are dating with an honest, open heart. I, by no means, am trying to discourage dating. I just want to draw attention to common mistakes and key takeaways I’ve learned while dating in this day and age.

I’ve been contemplating writing a blog on dating for quite some time. I’m not sure why I’ve put it off for so long or why I was scared to put my opinion on the subject out there.

Jessie… Scared?? What?! Are you shocked? Did I shock you – LOL? 🙈🤣

Anyway, yes, I was scared that if I put my voice on the subject of dating out there, I would blackball myself into never finding that special someone to share my life with. Stupid, I know, right?! I’m over here thinking that if I write a blog, some voodoo drama will happen. (LOL – must be the Louisiana in me!)

Whatever, I’m over it! And, I am here to share my experiences, because quite frankly, I need some single humans to read this and to learn something.

We live in a world now where dating comes quite literally right at your fingertips. With dating apps and technology, our options are virtually ENDLESS. It can make dating feel impossible and honestly, super depressing.

… And, what makes it even worse?

The dishonesty that comes with it all.

You may be thinking, “Dishonesty? What? What do you mean?”

Well, I’m talking about Ghosting. I’m talking about Back-up People. I’m talking about Lying.

I’m not here to toot my own horn or anything, but I am quite possibly too brutally honest for my own good sometimes. And, Yes, you guessed it! It has gotten me into trouble before. However, I would take a brutally honest person every single day of the week over someone who is trying to spare feelings.

In this modern day and age, dating can be super scary. There are some honest, good people out there looking for their match, but unfortunately you have to weed through a bunch of BS before finding them most times. I assume if you have found your way to my blog, it is either because 1) You think dating SUCKS, 2) You’ve been ghosted so many times that you are ready to give up, or 3) you are struggling with your worth and are constantly overthinking everything.

Regardless of what brought you here, my hope for you is that I can inspire you to speak your truth, to be honest, and to go into dating with an open, available heart.

Read that again.

- Speak Your Truth

- Be Honest

- Date with an Open, Available Heart

Those 3 points are the main focus of this blog post and I will be continuing to reinforce them throughout the post.

If you’ve made it here, you have made it to story time! Yay! (How mortifying LOL – Hopefully my not so fun dating history can help out in some way – so please enjoy!)

Now, with each story, my intent is to share some key takeaways and lessons I learned that hopefully can help others navigate dating better than I did when said story took place.

Story Time #1 – “The Original Pack of Oatmeal”

Alright, so in this story I shall call this man, Oatmeal, because this was quite possibly the most awkward, worst date I’ve ever been on. Wow, okay, I should take that down a notch, it was a nice date, but I had legit NO chemistry with this person at all.

The birth of the name of this story comes from the car ride home from my date. I was ranting! LOL – not angry ranting, but just rambling really. I could not find one thing I liked about this man, but I could tell he was so into me. It was tearing me up inside! The only way I could explain it was to say to my friend “Have you ever bought the variety pack of oatmeal? You know how there is a few different flavors, but there is always the Original pack of oatmeal in there too? You end up eating all the other flavors and then you finally get to the original pack and you’re like… I don’t want this. It’s so bland. I have to add something to it! It’s so boring!” Brutal, I know. But that is precisely how I felt in the moments after my date.

I kept thinking to myself, “Is this why people ghost people? Is this why people lie to spare feelings?!” The thought of having to be honest with Oatmeal and tell him I wasn’t interested was GUT WRENCHING.

Sure, he wasn’t my guy, but I’m sure he was perfect for another woman out there.

^^That point right there is EXACTLY why when you don’t feel a connection with someone you should be honest with them and tell them how you actually feel. In order to move on and find someone new, that person needs clarity and closure from you to find someone new. So don’t be selfish or try to spare feelings, BE HONEST. Now, I’m not saying you have to be brutally honest and give the exact reason why you didn’t like them, but just let them know that you are not interested.

The entire ride home I felt sick to my stomach. I knew what I had to do, but the thought of it was KILLING me. In that moment, I started to realize why so many people chicken out and ghost people. It’s easier than having to deal with the possibility of hurting someone’s feelings.

Want to know why I didn’t do that though? Why did I not just ghost Oatmeal?

Because I know how bad it hurts to not be told. Ghosting and Disappearing is just as hurtful, if not MORE hurtful, than being told the truth.

At least with the truth, you know that your date is no longer interested (who cares why?!) and can move on to someone new.

During the car ride home, I typed out a text in response to one of his texts that said how excited he was to see me again. I knew I would not be meeting up with him again and it was my duty to be honest with him.

“Thanks so much for the date. I had a good time, but I did not feel a connection. I don’t think it is a good idea for us to meet up again. I wish you all the best!”

EEEEK. BRUTAL. ACKKKK.

I know. I was so sick to my stomach. But, I could not lie. I could not ghost. I could not be like every man that had hurt me prior to this moment. I am better than that and I knew he deserved the truth.

To my surprise, he was unexpectedly gracious to me for my honesty.

“Hey, oh, okay, thanks for being honest. I wasn’t expecting that, but I hope we can still be friends.”

I chose not to respond to this text, because I had said my piece and, in my opinion, it was clear I had no interest in continuing a friendship with him.

Key Takeaways:

-Do Not Settle

If you don’t have a connection with someone, be honest with yourself and move on. There is someone out there who is better suited for you. Don’t settle for less than you deserve.

-Ask More Questions. Be honest with yourself early on when talking with someone.

In this specific situation, I had realized I wasn’t really interested in this man from the start, but I wasn’t asking important questions. I could’ve avoided this date completely if I had done my due diligence from the start.

-Be Honest. Brutally honest if you have to be.

Please note what I said earlier. You can be honest without being mean. You just need to be honest that you do not see a connection with them. Give them closure so that they can move on. You are going to be hurting them regardless, so don’t give them hope that you are an option, if you are not.

Story Time #2 “The Too Good to be True”

I’m sure we have all been down the “too good to be true” road before. With all the apps and technology, I am positive you can think of a person you started talking to and felt immediately enamored with them.

Whether it was the combination of their humor and good looks or their charming personality that got you, you got GOT.

This man (or woman) is the person you have been DREAMING of and now they are here! You are going to get married… This is the one, it’s finally ALL coming together…

You go on your first date.

Busy.

SOOOO Busy.

Ghost.

Am I being ghosted?!

You finally text them: “Hey, how are things?”

Them: “I am just soooo busy.”

Nothing aggravates me more than the “I’m busy” text. PLEASE. While I understand we all get busy (we do! We truly do!), NO ONE is too busy to update you if they like you. Whether it’s a nice good morning text or just an update to let them know you are still interested, no one that is interested in you is too busy for that.

Read that again.

If they are interested, they will NEVER be too busy to talk to you.

This is one of the hardest lessons I’ve had to learn, because it is really annoying!! 🙄 I say that, because, truly, I do not enjoy texting. I am a phone call / in-person gal through and through, so if I’m texting you, I like you. Because I hate texting. LOL

Anyway, there is nothing more frustrating than when someone you have grown to care for starts lying to you. They have gone from being so good to you, so reassuring, so caring… to busy, unresponsive, and dull. All of a sudden, they have no time for you.

Any time I have found myself in this situation, it has almost always resulted in me essentially asking them to tell me they’re not interested. I am just one of those people who refuses to be ghosted.

Of course, I’m not stupid. If I see all the signs and someone is drifting away, I feel it, but I just cannot stand the immaturity of someone not being honest about how they feel. Maybe that’s just me! Either way, if you ever find yourself in this situation, do not be afraid to ask for answers. If that’s what you need in order to move on, ask!

Do note that whatever it is they say could most likely be BS and they are just not interested, but still for some reason feel the need to spare your feelings.

Regardless of what they say, know that you need to move on and find someone who is more worth your time. If they do not respond at all, well, a non-answer is your answer.

And, remember, your worth should never be measured by that of someone else.

You are beautiful. You are worth it. And, you will find someone better. I promise!

Key Takeaways:

-Avoid creating the perfect person in your head and putting them on a pedestal before the first date.

I am SO bad at this. Truly. I have such a big heart and when I feel connected to someone, I just want to keep getting to know them more and more. It sets me up for a pretty big fall once reality sets in. I’m learning to keep my heart open yet guarded until I know someone’s true intentions.

-If after the first date, they are surprisingly unavailable/busy and are not willing to update you at all, they are most likely NOT interested.

I will start by saying that yes, it is possible for someone to be busy. I will finish this by saying no one is THAT busy. If they like you, they’ll find a way to reach out to you.

-Don’t be afraid to demand answers when you need closure.

If you are like me and NEED to be told that there is nothing there, don’t be afraid of asking for those answers. You may be wondering what happens if they never respond. Well, if they don’t respond, that’s your answer too… Not interested.

-Be okay with the classic “It’s Not You, It’s Me” OR the unforgettable “I’m just not ready to date” your date may present to you.

If you have dated recently, someone has 100% used one of the above on you. While it may not be the whole truth, accept it and move on. They’re not worth your time. I once had a guy tell me he wasn’t ready to date and then immediately got back on a dating site. Well. THAT was a lie! Lol – But in the end, it doesn’t matter. He wasn’t my man and a man who cares about me won’t lie to me.

As story time comes to an end, I want to circle back to the 3 main points I brought up early on.