Recently I wrote a blog post on my failures based on the concept of the “CV of Failures”. Inside, it contains key things or events I failed in.
I got a comment from a friend that it was still the “easy” stuff with only one line about my 3-year relationship that ended years back. Although the CV of Failures is largely career/skills based, the spirit of that concept is transferable. I missed the elephant in the room which is about relationship (attempt) failures.
Sometime back also, my female colleague once remarked “You are not even trying”. It was at that point I realised that attempts are rarely talked about. I mean people occasionally talk about their failed relationship(s) (including yours truly) in 1:1 or small groups. Much rarer are about failed attempts to start as that is considered quite embarrassing. Attempts specifically applies to men as ladies rarely make the move. (Assuming a typical heterosexual narrative here) If typical failures are already taboo, relationship failures on the edge of being off-limits, then talking about failed attempts in asking ladies out must be hell.
So let me go to hell this time to break what we deem to be a hugely embarrassing topic. I’ll not mention all the cases just the more recent ones that happened in the last few years. I see myself as quite systematic so I’ll mention the qualities I saw in the lady to make me ask her out, how the encounter roughly went and what I learned from it.
I know some guys will say “pretty or hot can already”. For me pretty or hot alone does not get me interested, I find that I’m most attracted to ladies who have one or more of these qualities; not afraid to get her hands dirty, have some technical capability and humble mindset.
I asked her because she was quite a cool techie and engineer. It was a huge regret I didn’t have the guts to ask her out earlier when she was still single. By the time I did, she was attached already. She did say she would have gone out with me if she wasn’t seeing anyone. I still consider her a close friend, someone I can confide with and get friendly advice from. Of course not in the romantic sense anymore.
The learning point from this is I should not delay asking.
I found her to be a gifted person at converting concepts into ways most people can understand. I didn’t know she was attached already but we still had a mature conversation. She was quite cool with it though and even suggested she can intro me if she knows anyone suitable.
She made a point that I felt was very quotable:
…it’s not to say that you shouldn’t put yourself out there and keep meeting people. You must keep doing it.
Effort matters a lot but sometimes you can’t choose who you can click with or end up being with. It may be someone completely outside of what you imagined you would be with.
I admittedly didn’t know her well but after that chat, I felt she was really friendly actually. Everyone is human too and have their own side of the story.
She’s the type of lady that is not afraid to get her hands dirty and with a humble character which I felt was quite endearing. When I asked her, she swiftly replied with all the dates she was free. I was truly impressed. I went out one time with her. After the first meeting, she told me she only saw me as a friend. Nevertheless, I felt we actually had many things in common except in the romantic sense.
I did meet up with her 2 more times in a pure friendship capacity and the conversations we had were interesting to say the least. Those I felt went better than our first meeting with the pressure off. I really made another great friend in the process.
In a later online conversation, we also talked about the Ladder Theory concept. She told me I was on her Friends Ladder and I was again impressed with her honesty and straightforwardness.
There is this notion that guys cannot be “just friends” with a lady he finds attractive. For me at least though, this doesn’t hold true and I learned I can separate out the romantic interest and treat a lady as a pure platonic friend.
These happened a long time ago and I had to dig out my “repressed memories” of these incidences.
She berated me from the get go saying I’m going out of my league. She used comments like ugly, skinny, nerd, look younger than her despite me being 2 years older. She also said I misrepresented my friendship with her by not making my intentions clear at the start. Well, I have to say she is honest…
I didn’t know she was attached when I asked her out. During that encounter before finally rejecting me, she compared me with her boyfriend and how good he was and how bad I am. The comparison felt unnecessary and left a bad taste as a simple rejection would have sufficed.
She initiated conversations with me multiple times beyond what I perceived to be the norm and often talked about my interests despite the fact that she seemed like a usually shy person. She also asked me if I was single, which made me wonder if it was a possible sign of interest on her part. However when I asked, she declined saying I wasn’t her type.
She asked me many personal questions like the schools I went to, my interests and the games I play. She also tried to help me do stuff. I asked but she said she was attached.
I might have just saw interest where none existed. Studies have shown men regularly misinterpret friendliness as sexual interest so I guess I’m part of this statistic. This brings me to a related point.
Ladies can make the first move
A friend of mine Lady H who is older than me confided that she was interested in a guy and was trying to talk to him to get him to make a move. She exclaimed:
“A guy, when interested to a girl, would do anything to make her speak or chat.. No matter how shy is he”
See the oxymoron there? The classic hinting and hoping the guy will get it and make the emotional investment to ask. I told her maybe she should try a more direct approach and straight up tell him since she is not getting any younger already.
She was stunned at first that such a possibility even existed. She said it’s not in her upbringing and might be assumed to be desperate. I said it’s the 21st century, no longer taboo for ladies to make the first move. Besides, I believe guys can appreciate just as well the confidence because I will.
To relate to the previous point, the hints that I thought were signs of interest turned out to be nothing in the end. Hints don’t work at least for me and possibly many other guys. In any case, I have to put lesser weight on hints since I might just be seeing what I wanted to see. Just be direct or not at all.
Say only though, in practice, this almost never happens for typical guys unless he is a celebrity or from a rich background (stereotype here). At least the option to ask is available for ladies. For men, asking is pretty much the only option.
The only ladies that have ever approached me are those that want to extract something from me. I had one lady who displayed overt sexual advances to “encourage” me to give her a certain benefit. Others have some “business ideas” but scream gender discrimination when I refuse.
Advice I got from others
Most of the advice centered along the lines of reducing my involvement in heavily male dominated activities like Repair Kopitiam, volunteering my time for Engineers.SG, being a Hackware organiser, doing so many exotic side projects and giving talks about them again to a largely male audience. Truth be told, I never really considered the repercussions when I diverted so much of my time away to those areas. I just followed my desire to contribute to the community and society in the best way I can as much as possible.
I don’t feel I’m the type at this time to use dating apps. I prefer to know the lady in person first and their qualities before asking them out. This could take at least several months or years before asking. Most of the ladies in this post can attest to this fact.
An “experienced” guy friend of mine also told me to not use a mental checklist if not “I’ll never be happy”, just go out and be willing to talk to people that I would not typically engage with. This is similar to what Lady B said as well. For me being an introvert, it’s really tough.
Writing this post was hugely demanding on my emotions as I had to recall as much as I could and put them into words. In an ideal scenario, this should not be, such failures should be seen as normal.
Asking a lady out even if she rejected me also granted me the privilege of having the most honest conversation with her that would not be possible under any typical scenario as friends. This I’m highly appreciative of.
I can’t say about the experiences of other guys because I don’t even know, testament to how taboo this topic is at least among my circle of friends. This made writing this post a bit of a challenge as there is no precedent for me to turn to.
In the perspective of my female colleague who made that initial statement, I can understand why she might say that. For women I guess, trying is just a matter of accepting one of the options on the table. Men on the other hand “trying” takes a whole new different meaning altogether.
To avoid issues, I did the logistically difficult and scary task to ask the ladies A, B and C whom I wrote in detail about my encounters to approve what I described of my interaction with them. There is one more lady but she was reluctant so I did not include my encounter with her.
I’m glad they were happy to accede to my request. I had to get their approval over several drafts before getting it right. I would like to thank my friend Lady H for being brave enough to let me use her as example too. Given the sensitivities of this post, I also appreciate the help of my closest friends for vetting this in its entirety after the ladies have given the green light to make sure there are no issues or avenues of misinterpretation.
I know some of you might want to guess who these ladies are. Please also do not speculate in the comments about who they might be. I’ll neither confirm nor deny even if you ask me directly. Their identities are not important, what I feel is the most important takeaway from this post is that I made this topic less of a forbidden subject and you can learn from it as well.