12 Lessons I Learnt About Dating After Going Out With 50 Guys

Dating Rules For Girls

I know what you’re thinking: 1) How did I even find the time to date 50 dudes? 2) I’m a lil bit rabz kebabz. For starters, I didn’t date 50 guys in one year and I began dating in my early teens.

I’ve had my fair share of dating mishaps but as Julius Caesar once said, “experience is the teacher of all things”. After 50 first dates, these are some lessons which I’ve gleaned.

1. Stop constantly assessing if guys are boyfriend material

It’s too much pressure if you constantly sort people into “BF potential” or “friendzone” categories.

When there are expectations, it’s difficult to have fun. You might also miss out on someone great because you think they’re not your type.

All good relationships are built on a solid foundation of friendship so focus on getting to know the other person first.

2. Cancel if you don’t feel excited about the date

If you’re not enthusiastic about going on a date with someone, just don’t. You already know you don’t want to meet him. Don’t waste his time.

3. Your first date outfit should be something you wear every day

First dates are nerve-racking enough, so wear something you’re comfortable in. An everyday outfit is a no-brainer because feeling good will give you a confidence boost.

In the past, I’ve wasted so much time on outfit changes, only to pick my default outfit: a black top, high-waist jeans, and black flats.

4. Late afternoon coffee is always a good idea

The only goal of a first date should be to know each other. Grabbing coffee is great because if the date is boring, you can stay the socially acceptable 30 minutes before making an ‘escape’. But if the conversation is going well, it gives you the opportunity to extend the date to dinner.

5. Ladies, always offer to pay

Be polite and prepared to pay for your own food. You’re a big girl, and you didn’t go on a date for a free meal. If you did, you aren’t seeing him for the right reasons.

 

Also read:

6. It’s okay to sleep with him after the first date

There isn’t a correct number of dates to wait before you sleep with someone, if it feels right, wrap it before you tap it. Sleeping with them does not make you a slut.

But you should know having sex can complicate a relationship. Some guys may think the act indicates the relationship will take a serious turn. Others think having sex makes you FWBs. So make sure to set expectations right prior to sexy time.

7. Make small talk if you want to be liked

It’s not hard—make eye contact, give compliments, share a common experience, then shift the conversation back to them.

Small talk is a low-cost opener which can lead to deeper conversations. Even if you’re not talking about anything significant, keeping topics light and breezy can make your date feel the same way.

8. If you don’t want to kiss him goodnight, don’t bother seeing him again

If you don’t feel like it, this shows a lack of physical chemistry and attraction. Take it as your intuition telling you, “this guy isn’t the one”.

9. You have the power to say “no”

You don’t have to say “yes” to going anywhere with them, or kissing them if you don’t want to.

You don’t have to pretend to like them back just because they’re nice.

You don’t have to reply if they send you 11.00pm “You up?” texts.

10. If you don’t like someone, don’t prolong the breakup

Not me, but one of my girlfriends. The dude she turned down? Solid chap. 10/10.

Sometimes, feelings change. When that happens, break it off cleanly and don’t lead them on. You owe it to others to be honest but polite.

Talk to them IRL. You can say something like, “Hey you’re a fantastic guy, but I’m sorry it’s not working out. I hope you’ll meet someone great.” If they react badly, know you aren’t responsible for their feelings.

11. Don’t try so hard to be nice

Many present their ideal selves on dates because they want to impress. It can make you come off as inauthentic, defensive, cold, or some combination of the three. This makes it hard to connect with your date.

Just be yourself.

12. “The only real dating advice is self-improvement”

You attract what you are. If you find yourself dating psychos, you’re probably emotionally unstable yourself.

Having strong boundaries and high self-esteem is the only way to attract quality people into your life. So before you build healthy relationships, work on yourself first.

Dating In Singapore

My dating journey has had its ups and downs. Many were one-date-only dudes; they were nice but there wasn’t chemistry. Some I dated for a while before realising we made better friends. Others, I fell in love with.

Ultimately, don’t take it too hard on yourself if a relationship doesn’t work out. And hopefully, learning from my dating experience will help your love life run smoother.

Cover image: Studiaorontica.org
This article was first published on 21 December 2018 and last updated on 10 January 2024.

Also read: