I got back into dating and here’s what I’m struggling with

Putting yourself out there again, whether you have been out of the dating game for a few weeks or months, is scary as hell, especially if you’re not sure how to start dating again. After a breakup or a long dry spell, the prospect of meeting someone new, going on a date and opening up again can be daunting. So, where do you even begin?

You read about my “heartbreak” and also how to show yourself a little more love, a few months ago, so you have been along for the ride. So I figured I would share with you how I got back into dating and what I have been struggling with.

Not being sure if I am ready or what I want

I have been single for a while. It’s actually been so long that when I tell people, they look at me in shock. Given how long it has been, I should be able to tell if I am ready and what I want. But I am often torn between wanting a long-term relationship or a cheeky hookup. Serious things are in my nature, but do I have time for them right now? Because I have so many things going on in my life at the same time, would it be fair to the other person if I start something serious and then do not have time for them?

Letting my guard down and being myself

It could be my upbringing or previous relationships, but I have a hard time opening up. That means the other person may perceive me as cold and closed off, when that couldn’t be further from the truth. I am an over-sharer and also very affectionate, but when it comes to getting to know someone new in a romantic sense, I do need some time before I can truly be myself. It is understandable that someone might be put off if they do not feel like they are getting back what they are giving. I am trying to find a happy medium where I can be more open without completely letting down my guard and allowing myself to be hurt again, which actually scares the life out of me.

Not knowing what to say or how to shoot my shot

I would like to think I am quite chatty and entertaining, but starting a conversation with someone, whether in person or on a dating app, is something I despise. I am one of those people who say, "Hey, how is it going?" because, first and foremost, what am I supposed to say, and second, why waste time coming up with something better when they might not even respond? I am, in fact, my own worst enemy.

There have been multiple occasions when I was out or at work and I found someone attractive. Do you think I went and approached them? Hell no! I am terrified of rejection, so approaching a stranger, when they may or may not be interested, is a big no from me. I’ve promised myself I will step outside my comfort zone a bit more this year, and I am hoping that will lead to me shooting my shot more frequently. After all, what is the worst that could happen?


I already said I am my own worst enemy, and this is especially true when it comes to my brain. I will over-analyse the simplest of things, causing myself to freak out and question everything you may not even consider. That is definitely not a good thing when it comes to dating, and while I am working on it, I have always been an over-thinker, and it is not something that will change with the snap of a finger.

Also, a quick note for my friends, please stop telling me to stop overthinking. I swear, if it was that easy, I would. As a woman I have the ability to multitask, so even if I am crazy busy, I will think about the thing I shouldn’t be thinking about.

Expecting too much and putting too much pressure on it

I think one thing, but my brain thinks another. That sounds like me and my brain are two separate entities, and I am beginning to believe so. I re-entered the dating scene with the intention of meeting new people. Not necessarily to find the love of my life, but to go on a few dates, gain some confidence, and so on.

And after each failed talking stage or date, my friends tell me that I am putting too much pressure on it and that I should not be looking for "it" because it will find me. But am I looking for anything in particular? "I need to put myself out there," I always say, "because Prince Charming will not just come looking for me at my house."

But I do see their point, my problem is that I expect others to treat me the same way I treat them. If I am giving honesty, that is exactly what I expect back. And unfortunately, that’s not how it goes. So you will be ghosted, and you will be lied to, but that is no reason to give up and shut yourself down again.

Consider dating as an opportunity to have fun, meet new people, and get a little ego boost if you need it. And if anything else comes out of it, fantastic!

Not learning from my past mistakes, ignoring red flags and wearing the so-called "pink glasses"

I will always put on the "pink glasses" and romanticise everything. And when I wear those damn glasses, it is as if I forget what I have learnt in the past or the obvious red flags. I am aware of it in the back of my mind, but I choose to ignore it, most likely in search of love. That is pretty stupid for someone as smart as me because I see the pattern, I see the person waving the red flags right in front of me, but what do I do? Yes, you know it.

Putting all my eggs in one basket

I will just come right out and say it: I am an idiot. If you’ve had a break from dating, no matter how long, the last thing you should do is put all your eggs in one basket. Get to know more people and see who you get along with the best. Do not focus solely on one person with whom you have a connection and ignore everyone else, as I did. Cast a wide net to see what is out there. I recently told a date that I am guilty of doing this and that I should go on more dates because focusing on one person is a "waste of time."

That may sound harsh, but what I mean is that if you are getting to know multiple people at the same time, you are not just focusing on one person for weeks or months at a time and having to start over if it does not work out.

Nervousness and lack of confidence

Oh, the nerves! It is almost comical how nervous I get before a first date. My hands are sweating and shaking, which they never do, my voice is trembling, and I honestly feel sick. I remember I had to have a few drinks before going on a date last year to relax a little because I was sh**ting myself.

This ties into my almost non-existent confidence, so it is probably no surprise that I bloody hate dating. That, combined with overthinking, makes it extremely difficult. But, you know, I have been told several times that I appear to be quite confident, so I guess I am pretty good at faking it.

And the best advice I can give to anyone, no matter what the situation, is to fake it until you make it. If you manage to present yourself as calm and collected, no one can find out what’s happening on the inside.

What things do you struggle with when it comes to dating? Let us know in the comments!