Lessons I’ve learnt from dating.

Monica S
10 min readJan 11, 2024

We all know that life is full of learning curves and experiences that help shape who we are. Some of us learn faster than others, whilst some never learn at all. I’d like to think that I’ve learnt a hell of a lot since I started dating at the age of 18. I’m now 32 and I feel that I know so much more now than in my late teens and 20’s. Even a few years ago I was naïve and idealistic. Here are some of the lessons that I’ve learnt from dating.

1. An ex is an ex for a reason (in 99% of cases).

This is a hard lesson that I learnt with my very first ex. I was so gutted after we broke up and was desperate to get back with him. I tried everything to get him to want me again (he didn’t want me). I wasted so much time and effort on him. Even if he had wanted to get back together, it wouldn’t have lasted. We were too different. Aside from the initial chemistry and spark, we had nothing in common and our personalities clashed.

After my next relationships ended, I got over the break ups far more easily. I didn’t waste any time pining over my exes. I quickly realized that the break ups were a blessing in disguise. I also saw the break ups as an opportunity to reflect. Having that distance and space to reflect made me realize how unhappy I had been. The first break up was the hardest because it was my first. If I had gotten together with my first ex now, we probably still would have ended up breaking up, but I probably would be nowhere near as upset as I was then and I’d get over it much quicker. I thought he was perfect for me at the time and that I had missed an amazing guy, but in hindsight, he definitely wasn’t so amazing.

2. Don’t chase after someone who doesn’t want you.

I spent far too long chasing after my first ex who didn’t want me anyway. I also spent my 20’s chasing after guys that weren’t interested in me. I thought that it I kept preserving that they would eventually want me. Even if they showed no signs of wanting a relationship with me, I still thought I stood a chance if I played my cards right. I definitely had very low self-esteem back then.

Looking back, it was very humiliating for me and even if these guys would have wanted me, they weren’t the kind of guys who would have treated me right. I’m done with the bad boys and the thrill of the chase. It’s not even that thrilling to be honest. I’ve learnt that if a guy doesn’t want you, it has nothing to do with you. It doesn’t mean that you’re unworthy or undesirable. You deserve someone who is crazy about you. You shouldn’t have to chase anyone or try desperately to hold onto them. If a guy makes you chase him, it shows that he’s immature, insecure and a game player.

3. Self-confidence is key.

I spent my 20’s riddled with insecurities. Vultures always prey on those with insecurities. My insecurities landed me right in the clutches of a narcissist. If I had presented myself with more confidence, I don’t think he would have shown any interest in me. He used my insecurities against me and messed with my head so much that I became an empty shell of a person.

I allowed him to convince me that I was crazy and that no man would want me. I allowed him to talk me into having a mental illness I didn’t have and my therapist definitely didn’t think I had. I allowed him to criticize every little thing I said and to take the blame for his mistakes.

However, that experience has taught me that I’m worth so much more and that my ex was the crazy one. I learnt that I didn’t deserve to be treated like that and never to allow anyone to make me doubt myself.

On the other side, lack of confidence is unattractive and off-putting. I would constantly go on about how “fat” and “ugly” I was in front of guys. I definitely wasn’t fat and I’m not ugly. Nobody wants to hear someone ramble on about themselves and how much they think they suck. Insecurity can be very draining and takes the fun out of spending time with someone. My last ex-boyfriend was very insecure and it was very draining having to constantly reassure him. He wasn’t very fun to be around.

4. The dangers of love bombing.

Just because a guy showers you with compliments and tells you what you want to hear, it doesn’t mean that he’s the Mr Right you’ve been waiting for all your life. Whilst it’s nice to receive compliments and to be on the same page about things, the actions need to match. If a guy is telling you how amazing and incredible you are and how much he wants to be with you, but ignores you for days and disregards your feelings, that’s not a sign of someone who truly adores you. Someone who adores you doesn’t constantly criticize you, gaslight you or make you feel uncertain of where you stand.

Material things also aren’t a sign of how much someone cares. Though stinginess is a red flag too. My narcissistic ex was stingy AF and never bought me a coffee let alone a gift! I bought him stuff but he never got me anything! Although a guy shouldn’t have to or be expected to pay for everything, it’s a nice gesture to buy gifts and pay for dinner and drinks sometimes.

Bombarding you with gifts and paying for everything can seem flattering, but it’s something that you should be careful about. Some guys use gifts and money as a way to buy someone’s affection, interest or forgiveness. Think of the guys who cheat on their wives or beat them and buy them expensive things to get their forgiveness. What’s the point of nice gifts if you can’t be faithful or treat someone properly?

My last needy ex was generous with gifts and money. He wouldn’t let me pay for anything. Whilst it was nice, it meant nothing as he ended up breaking up with me and told me that “the spark wasn’t there anymore” shortly after telling me he loved me and begging me not to leave him.

5. Attraction isn’t everything.

I admit that I was quite superficial in my 20’s. I was more hung up on looks than personality. I chased after the good-looking jerks. I still do believe that attraction is important, but personality is more important. As long as there is some attraction there, it can grow. I wasn’t initially attracted to my last ex but my attraction to him grew. I thought he was kind and respectful so I gave him a chance. My narcissistic ex was conventionally extremely attractive (tall, dark and handsome), but he was an ugly person. He was extremely arrogant and only into himself. He loved to talk about himself all the time. He wasn’t funny, kind, generous, loyal or supportive- the traits that I look for in a guy.

I recently hooked up with a guy friend of mine (not really a friend anymore) and although he’s not my usual type, as I spent more time with him, I grew more attracted to him. Also you can be pleasantly surprised. I discovered that he actually has a good body. Unfortunately things got messy between us and he doesn’t know what he wants in life, but I’m over it. In my 20’s I would have chased after him and been desperate for him to want me, now I don’t care. My point anyway was about how attraction can grow, but there does have to be some glimmer of attraction there.

6. Don’t ignore your instincts and don’t force something if you’re not sure about it.

With my recent exes in particular there were a lot of red flags, especially with my narcissistic ex. There were a lot of things that didn’t sit well with me and made me feel uncomfortable such as some of the things he said and how his words and actions didn’t match. Some of his views were really extreme and shocked me, but I thought that I could change him. Towards the end I felt really scared of him.

My most recent ex was less extreme, but his family dynamic and relationship history made me wary. His father cheated on his mother when she was alive and he fathered another child with another woman that he refused to acknowledge. His father was in an open relationship with a woman half his age! My ex didn’t think that there was anything wrong with what his father did to his mother and claimed that his father “was a good husband in other ways.” He wasn’t even shocked to find out that he had a half-sibling!

My ex also had twenty short term relationships. When I confronted him about him, he said that was in the past and he was looking for something serious. I also felt that we weren’t compatible and that he was too intense, but I decided to give it a try because he seemed kind.

I don’t regret giving it a try, but it’s taught me to trust my instincts and not to ignore the red flags. Whilst nobody is perfect and we all have flaws, if there are things that make you worry about the future of the relationship such as different values and beliefs, or behaviour that is extremely off-putting and problematic such as arrogance and emotional immaturity, don’t hesitate to call things off. Trust your gut and don’t think that you can change a person. Don’t waste your time if this person is draining you and not making you happy. With my narc ex I was miserable AF. With my recent ex I wasn’t completely unhappy, but I wasn’t completely happy either. If someone isn’t making you feel truly happy, you should seriously question whether this relationship is right for you.

7. Don’t change yourself for a guy.

When I was younger, I would have changed myself just to make a guy happy. I thought that if I was skinny, more guys would want to be with me. I thought if I made a guy wait for sex, he would see me as girlfriend material. I wished I was like other girls like their ex-girlfriends or girls they did see as “girlfriend material.” I thought they’d like me if was cooler or had a different personality.

I feel sad for my past self for thinking so lowly of myself. I was good enough. I would have loved to have told my past self that I am worthy and that I should embrace who I am. If a guy doesn’t like me for me, that’s his problem. These guys probably don’t respect any women even their exes or the girls that they supposedly see as “girlfriend material.”

I also tried to change myself for my narc ex and ended up losing myself completely. At first he claimed that he liked me for who I was, only later to tell me that he didn’t like very much about me at all. At first he said that he loved that I was opinionated and feisty, only then to say that he didn’t like those things about me.

8. Your type can change.

If you think back to your first crush, you’ll probably laugh. My first crush was a tall, skinny guy with long floppy hair called George. Would I go for him now? Definitely not. It turned out that he didn’t have much personality anyway and wasn’t the sharpest tool in the shed. When I dated my first ex and my recent ex, I thought that I liked the overly sensitive, emotional and brooding type. Nope those are not characteristics I found attractive in a man. I just want to point out that there’s nothing wrong with being emotional and sensitive, but a guy who is overly emotional and sensitive is not for me.

I thought that tall, dark and handsome was everything when I dated my narc ex. Tall, dark and handsome is overrated anyway. In my mid-twenties I decided to embrace my Jewish heritage and become fully Jewish, so now I only date Jewish guys because those same values and traditions are important to me. In the past when dating, religion and culture weren’t important to me. My younger self never envisioned that it would be something that would change.

9. There’s no such thing as the perfect guy.

Hollywood has people believe that the perfect love exists, that relationships need to have sparks and fireworks all the time and that a person should meet all of your criteria. Also a guy can appear to be perfect like my narc ex, but the exterior can be very deceptive. There are other guys who I thought would be perfect for me only to discover they were definitely far from perfect and extremely fucked up!

Whilst it’s important to have standards (definitely don’t date a guy you know you won’t be compatible with are and are repelled at the idea of sleeping with), having those common core values are the most important thing. So what you don’t love his haircut and he’s a bit nerdy? How does he treat you and other people around him? Does he make you laugh? Do you have a good time together? Does he grow on you the more you spend time with him?

So those are my top lessons. Which ones do you identify with and what dating lessons have you learnt? Let me know in the comments.



Monica S

I love writing. I may be controversial but I'm not afraid to say it how it is.