Singapore Office Lady2

5 Lessons Learned Dating an Intimidating Singaporean OL

I recently scored a date with the stereotypical: Singapore office lady. The tight office dress, intimidating front, the expensive looking bags. I met her in one of the clubs. She stood there, high heeled, with her fierce looking friend, and I told myself to balls up, and I approached her.

I actually appreciated the fact that I was going out with a girl I was sexually attracted to. I haven’t been on a quality date in Singapore since I came back from Japan.

5 Lessons Learned Dating a Singaporean Office Lady

Dating her was a surprising experience. Here are the lessons I took away from the dating her.

1) Texting is Overrated, Just ask Her Out

Over text, our conversations were the boring, blunt and short. It was to the point that I had to call her out: your replies are short sentenced, come on, this isn’t going to work out. My old pick up artist instincts were going off. She isn’t into you. Every attractive girl is texting 10 other guys, and what so special about you? I thought she wasn’t interested and was texting 10 other guys at the same time.

Our conversation eventually died out at one point, and I was hating myself for letting his girl go without asking her out.

I decided to take another chance and asked her out. Here’s my text conversation:

“Yo, what’s up for your weekend”
“Wanna grab coffee or tea and chill”

It’s direct, to the point and boring. Surprisingly, she agreed.

Important pointer, just ask a girl you’re interesting in out, face the impending disappointment or rejection. If you’re going to be rejected, so be it, at least you found your truth.

2) Not all Hot Girls are That Scary

She showed up in an office dress (as she came from a wedding) and slippers, Singapore office lady style. I was wondering if she was how she’s like in real life conversationally: one sentence styled of boring and blunt. Like her text messages.

No surprise there, she’s boring.

I’m starting to think if it’s a Singaporean thing. Or is a hot girls thing? Hot girls spend their whole lives with guys deferring to them. The guys are always asking them questions and not needing to be the ones adding to the conversation. Hence, these girls never built the conversational skills to connect with others on an emotional level.

On the other end, I had spent the last 5 years reading up on self-help books, and I’m pretty strong conversationally.

She floated away to social media from time to time and added rarely initiated in conversation. Relating to her as a human being was a total bore. I was disappointed in that sense. I was expecting much better. Since she’s one of those academically inclined girls, coming from a local University background. I thought I’ll be in able to stretch my intellectual muscles with her. I quickly learned that most girls aren’t going on dates to have nerdy talks with you.

I also somewhat overvalued the office lady exterior. The flashy hand bags, and the flashy credit cards. She was also from a top University in Singapore, so I was feeling a little insecure about that.

I was thinking to myself: I’m just a student, freelanced on some web design projects, for the past 2 years, who am I to be dating some classy Singapore office lady? Yeah, I read a little and see myself as someone who an intellectually curious individual, but I don’t have the external success to back it up. I guess these are my insecurities.

Singapore Office Ladies

Don’t Be Intimidated by Their Stone Cold Exterior!

3) You Should Know what You Want Out of The Date

Should I merely continue to hit on her despite not feeling a sense of connection? It felt meaningless after awhile. I had been consciously looking for more commitment in my life and was looking for a more exclusive relationship. This is because a longer term and stable relationship are going to be more suited for current needs. I wanted to do well in school and I want to focus on being a Singapore dating coach.

The metric of success should be happiness.

However, at the same time, she’s attractive and I wouldn’t mind hooking up with her. I’m torn between emotions.

That’s the thing about dating, not every girl is going to 100% fulfilled your emotional needs. There are some girls that are going to make you feel sexually attracted, but not connected or appreciated as a partner. There are some girls that are going to make you feel really secure in a relationship, but perhaps you’re not going to feel as excited to be with her.

When I left for home I was asking if I should text her again? Should we try again on the second date?

4) Be Comfortable with Your Sexuality

I wasn’t really physical or touchy during the date. That’s because she’s older than me and she was wearing office wear which intimidated me a little. She also wasn’t talking a lot so I assumed she was unattracted and bored on the date.

However, she gave me quite a lot of indicators of interest physically. She stood really close to me and was okay with my physical touches when I teased her. I was thinking to myself: perhaps that’s how she showed her interest. I showed my interest through words, and she showed her interest through touches.

I haven’t been on a movie date since I got into this pick up and self help thing, that’s because it’s said to be boring and there’s no chance for physical intimacy or conversation. However, this time round, there’s this movie that both of us wanted to watch and she’s said she haven’t watched a movie from the cinemas for years. During our movie together, she even leaned on me slightly during the movie.

It’s more important for us as the man to polarise the interaction and figure out the truth, than wait for the green lights. The majority of dating advice (arguably, some of the pick up artist content out) depends on us reacting to the girl, and adjusting our behaviours according to hers, instead of taking charge and figuring it out ourselves.

Perhaps she isn’t looking to connect with anybody emotionally at this point of her life and just wanted to date around? However, she’s not going to say anything that makes her look like a slut. Girls are human beings and have sexual desires too, but society makes it hard for them to express them socially. This is especially so for a traditional Asian centric society like Singapore.

This is can be quite true for Singapore. Girls here can be quite shy and non expressive. The biggest indicator of interest is that she’s out with you, and not somewhere else. Looking back, I had tons of tons of times where I was out with a girl and didn’t notice the fact that she’s actually interested in me. I thought we were just ‘hanging out’.

Is it wrong or bad to say that you can’t be sexually attracted to her without being emotionally connected to her? That’s dependent on your own values and needs. I always felt that I could not go for a girl that I couldn’t feel emotionally connected with or have a meaningful conversation with. That’s just me.

I also figured that there’s you can’t get all needs met at once. Some parts of her and your identity are going to take time to develop. The only thing we can control is our own behaviours, and how you express your identity to her.

Office Lady Singapore4

5) Be More Assertive and Go For What you Want

On this date, I made the mistake of choosing places where it’s hard to seat beside her. She was pretty easy going with the places and I should have been more assertive with the places where I can sit beside her where it allows for physical intimacy.

The layout in most bars and coffee places in Singapore are often planned out where you sit across each other. It only allows for conversation and not physical intimacy. I’ll just sit beside a girl next time on a date. If she asks why I’ll just say: cause you’re pretty and I want to sit beside you.

I’ve mentioned that my approach towards girls has been more connection based, rather than sexual based. I probably don’t touch a girl enough or attempt to escalate the interaction physically enough. Either that, I miscalibrated and escalate too quickly at one point of the interaction.

Furthermore, the more feminine the girl is, the more you’re going to be expected to lead physically. She’s not going to initiate for you.

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