Hindsight & Life Lessons

Sometimes I get frustrated with my lack of progress in dating. I’ve been on the apps for a good few years now but it’s been a fruitless endeavor. Sometimes I worry that I’m going to get older and it’s just going to get harder and harder.

But as I was reading through a post on The Rules Revisited yesterday, I realised that age and dating mishaps bring one advantage: experience. With experience comes lessons learned, that can help you in your dating life moving forward.

However if you’re young and inexperienced, you can get ahead of the game by learning from other people’s mistakes. So here are the scenarios I’ve encountered during my dating life, and the advice I’d give to myself with hindsight and experience, and hopefully if one of you encounters a similar situation you can benefit from my pearls of wisdom.

hindsight and life lessons

Age 16

I’d fallen hard and fast for a guy in my Friday night drinking group. We’d kissed a couple of times, but we were yet to go on any kind of actual date. Every night I’d dress up, hang around with him, talk to him, but nothing seemed to be progressing. “He likes you!”, my friends told me. “You just need to show him you’re interested!” But I WAS showing him I was interested. But nothing was happening!

26 year old me’s advice: He’s not interested. Drop him and move on. If you can’t move on without closure, tell him you like him then get rejected. “I’m not sure” is a rejection.

You can find out how this situation actually worked out here.

Age 18

I quite fancied a guy in the block next to me in halls. We’d kissed a couple of times but he’d told me straight up from the start that it wasn’t going to go anywhere and I’d accepted that. However, he then began sleeping with one of my friends, my friend told him I liked him, and after that he started ignoring me. My ego was CRUSHED, and the more he ignored me, the more I liked him. One night, I decided to get with someone else to try and move on, and ended up getting with this cute security guard. But getting with someone else just wasn’t the same and I still liked the original guy!

26 year old me’s advice: Ignore the guy, drop the “friend”, and pursue the cute security guard. You’ll find out later that he’s actually pretty cool but by that point he’s graduated.

Age 19

I liked a guy, he liked me. He had a girlfriend the first time we kissed, but he’d now gone on a break with her and wanted to break up with her. We’d kissed again, we’d texted, we’d met up, but he still hadn’t formally ended it. What to do?

26 year old me’s advice: Be straight up with him, tell him you want to be with him but he has to be fully single. If he doesn’t break up with her he’s either not interested or completely gutless, so drop him.

You can find out how that situation actually worked out here.

Age 23

I liked a guy, he had a girlfriend. But we talked all the time. We flirted. His girlfriend wouldn’t relocate to be with him. I wanted to relocate. If only he’d met me first. I was going to visit him soon. Perhaps something could happen?

26 year old me’s advice: You’re in the fuckzone. Even if he was single, he wouldn’t be interested. Drop him and move on.

You can find out how this situation actually worked out here.

Age 24

After things went tits-up with the above-mentioned guy, I because conscious of the fact that I was going to hit the big 2-5 next year without a husband in tow. I’d been doing online dating and dating apps for a couple of years with no success, but I decided to up the dates. I was having countless dates, but kept meeting either “nice enough but wouldn’t get with”s or complete weirdos. I was losing the will to live.

26 year old me’s advice: Improve your profile and be more picky about who you meet. Don’t go unless you at least think you might fancy them from pictures. Quality over quantity.

Of course, there’s always the danger that you may start liking someone and all logic flies out the window. But no matter how intense the chemistry, make sure to apply all previous lessons learned and good dating advice you’ve read online, and your sanity will be much better for it.

What advice would you give your younger self with hindsight? What lessons have you learned? Let me know in the comments!

3 thoughts on “Hindsight & Life Lessons

  1. I’ve learnt to always place “Does he treat you right, like how you would want a man to treat your best friend, daughter etc?” as the first key criteria when filtering men. If he doesn’t do so, it doesn’t matter if he is the most talented, handsome, charming or family guy that you met. It just doesn’t matter. Always put yourself as the priority. 🙂


      1. Been there done that! What I learnt was there is always a better guy who will treat you right, you just gotta let go of the one who doesn’t!


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