The long and short about Why You Should Date An Older Woman

Even the best plans made by a Man of Action can go haywire if the circumstances doesn’t allow for it. Although I’ve made up my mind to ask Ms Tan if she was the one who gave me the bean curd, I was unable to because she was sent on an urgent overseas working trip since Monday. She will be back tomorrow though, and I hope my queries will be answered then.

Anyway, I’ve been wondering what I should do if Ms Tan confesses her love for me. As with the situation I had with Office Bimbo, I think it’s a big no-no because it’s not a very good idea to take a shit in my own backyard. And with Ms Tan, there’s this added dimension of complexity because she is an Older Woman.

I hate to say this, but there’s a whole lot of social stigma attached to dating an Older Woman. While society is generally accepting of a guy dating a gal six or seven years his junior, the same cannot be said for the reverse. The last wedding dinner I was in, the guests started murmuring when it was made known that the bride was two years senior than the groom. This is bad because if we ever get married, the crowd might start rioting because Ms Tan is older than me by almost a decade.

I think this is very, very bad. Older Women are human too, and I think there should be no reason why they get stigmatized when Dirty Old Men bedding Sweet Young Things get away with it. I will take my small step in trying to change this perception by coming up with a list of reasons why you should date an Older Woman:


Reason #01: She is richer
According to this Straits Times article some time back, 40% of Singaporean female graduate above 30 are single, compared to 10% for females with less than secondary school qualifications. The main reasons cited for this disparity are higher expectations, and because that family and love takes a backseat in favor of career for the better educated. That seems to be the case for Ms Tan too, and I bet she will be able to provide me with the life a Male Tai-Tai if she wants to. Heh.

Reason #02: She is wiser, wittier, and sassier
I am making a lot of assumptions here because just because someone is older, doesn’t necessarily mean she is wiser, wittier, or sassier. But given that they may have traveled more and had more time to learnt about the wonders of life, the possibility of them being wiser, wittier, and sassier, is higher.

Reason #03: It is romantic to date an Older Woman
Be rebellious! Flout conventions! Follow your heart and date the Older Woman, like what 楊過 did for 小龍女.

Reason #04: She can teach you things in bed
This point was actually brought up by the very unorthodox Nerd when I told him about my situation. Unfortunately, I think it doesn’t apply to my situation because I think Ms Tan is a virgin like me.

Reason #05: You can die together
This point is rather morbid, but makes a lot of sense. The Superior Species have a higher life expectancy than guys, so the chances of you dying in your sleep together ala The Notebook is much higher.


I was telling Sushi Eating Friend that actually, come to think of it, there are not a lot of compelling reasons why you should date an Older Woman. But she shut me up by saying “I think if you really love someone, you shouldn’t give a hoot about how old or how young she is.”

Oh well. I have a wise, witty, and sassy friend.

With Love,
Sibeh Sian