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Sunday, July 21, 2024


Hey friends,


Not sure if you can relate, but I’m feeling the dating fatigue lately.

So I was discussing this with a few friends actually and they all had some differing opinions but figured out this community can probably give me a more unbiased and diversified answer. I’m over that 30 yo benchmark as a guy and to be honest I’m really feeling that crisis now. I’m single, went through 2 breakups while I was younger, last relationship ended about 2 years ago. I had to undergo quite a bit of family issues the last 2 years and they’re finally somewhat resolved and settled.

Started dating again and found myself getting weary. My main mode of finding people is through online dating apps like Hinge/CMB/OKC/Tinder. But my experience so far has been so suboptimal compared to when I first matched with my ex many years ago. It feels almost dead in a sense – I’d get maybe one or two replies and the conversation does not really continue past that. Online dating works for me due to the hours I work every week (about 60-80 hours).

At first I thought it was just me not being good enough you know, or not having my shit together, so I worked on myself – so I literally started working out, I think I look decently fit, I’ve worn better clothes/am cleanly groomed/etc, I read a ton of books, started getting ahead in my career, went for improv classes, joined some classes to learn stuff and socialise more… Last date I had I thought I had a really good connection with. Then it ultimately came to the “I’m not good enough for you, I have some stuff to work through” variant where I’m ultimately friend-zoned.


Tbh I think I set reasonable standards on dating – I don’t expect much of it, I let the date go as it should, I have reasonably good conversations without awkward moments with deep connection, I often hit 2-3 dates before it falls apart. My dates would tell me that they genuinely enjoyed themselves and we’d always make it to the next date. Then I thought to myself, maybe I’m too nice? But I don’t think I should compromise on my own principles of just being generally kind to everyone. I don’t think I’m a people-pleaser either, neither am I trying to get something back in exchange for being nice. It’s just that I’ve been getting this “you’re too nice and I’m not feeling the vibes” thing too much and realise that it’s becoming a problem. The thing is, I do stand my ground, I have solid boundaries of what I like vs dislike, I have principles, I know what I don’t accept in my life, etc – I don’t get it about the whole nice guy thing because I’m not that “agreeable”?? Or is the standard of nice just too low

Some dates I’ve spoken to also seem to be believe in “The One”. I kinda believe in a half – and that the rest is about building the relationship itself. My last date told me she had 5 other people she was seeing, and tbh I don’t think it’s a surprise given I’ve seen some of my female friends and sister have close to a 100 matches and 10 convos going on simultaneously. But yeah the competition is real.

And of course there’s also that whole issue about finances – while I understand I can bring a lady out to a kopitiam (I brought an ex to a kopitiam), I’ve found most other dates to really be more comfortable over a coffee in a not-so-ex cafe. But the costs do add up with the brunches and stuff. Stick that over 10+ dates within 1-2 months and it gets pretty weary and costly. My last date brought that up and tried to pay for everything but I still felt that I had to at least pay for the meal or at minimum go Dutch. I also think that I’m the kind that tends to fall pretty quickly (though I control it a lot), so this dating business isn’t very good for my heart, I think I’m just headed in a bad direction for becoming jaded.

I think I have a few questions, some of which I’ve discussed with friends. Some friends have had similar experiences also and are basically in a jaded FA mode. I’m really curious to hear what you more-experienced guys and ladies think:

  1. What do you think of the dating scene in Singapore? Is it more difficult for average guys to find a connection? Is it really just a numbers game?
  2. What am I not seeing about this whole “you’re too nice” or “I’m not good enough” dynamic that I’m not seeing and totally missing? What can I do?
  3. What is your stance on deal-breakers – how many should you have? Deal-breakers meaning things that you really cannot stand for.
  4. What do you think about dating multiple people at once? Does it turn people off?
  5. Anything else you want to know, or ask, or share your woes about :’)


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