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> Dating Over 30, Share your experience

post Mar 31 2020, 05:09 PM

Junior Member
443 posts

Joined: Aug 2010

Phase 1 (<20):
wasted too much time (3 years) chasing after 1 girl during college. In the end didn't manage to get anywhere. Nothing much gained here. No experience. Only learnt to be a better and caring person. (instead of self-centered, childish and short tempered)
Girl Age: 16-20 My Age: 16-20

Phase 2 (20-30):
Idle for very long because was quite heart broken due to phase 1.
Tried going after 4 girls (not concurrent), (friend's of friend, waitress, app)

After a long while of heart broken (yea that time noob. dunno how to let go) finally decided to approach friend's friend. Got very close, almost succeed, but her family know and they strongly object us together. (cause she 3 years elder than me, and that time i've only started my career for 4 years, so not that stable yet)
Girl Age: 26 My Age: 23

was again dejected for a while (2 years?). Then again met another friend's friend. Chased after her for 1 year and finally she became my 1st gf. But ultimately we're worlds apart (totally different lifestyle and mindset) and it's only by sheer accident (literally) that we got together. So naturally she felt that I'm not the guy that she looking for, and we broke up.
Here I learnt, no matter how much you love a person, you won't be together if:
1. you two are too different (and one or both party was unwilling to bridge the gap)
2. she does not have much (or enough) good feelings / vibe towards you. After a while, it turns stale.

Tbh, this is the girl that i once loved the most and i was seriously heart broken about it also. I think i took about 2-3 years to recover from it and was seriously down (cried alot) during the recovery stage.
Girl Age: 28 My Age: 26

After 2-3 years, I finally decided to move on, and tried knowing more people, met a waitress, had a chat with her. follow up few times, went out date 2x, but didn't work out.
Again, worlds apart. Didn't manage to start anything at all.
Girl Age: 22 My age: 29

Met a girl at CMB. We clicked very well. but after a while, i got together with my current GF. So we stopped contacting.
Girl Age: 24 My age: 29

Phase 3 (29-31)
This one complicated a bit. Basically I'm interested in her, we went out for quite a while. Clicked well. But there were some parts that I wasn't sure if we will work out.And after a while, I realized that she had no prior experience in relationship. And I thought to myself, since i was hurt so badly for my first one, and if I can't be damn sure that we both will work out, I better don't hurt this girl by "trying it out". So i kept my distance.
But the girl is still keen. then after a while, i decided, screw it. give it a try, give it my best. We continue going out again, then i decided to move to the next stage, prepared and ask if she wanna be my gf. but she didn't give me an answer and i felt confused. I thought she had no interest to move on to the next stage.
And so on and off, I was given mixed signals, until we finally sat down and discuss about our potential concerns and if we want to proceed to next stage knowing these concerns.
Ultimately, we decided to try things out and it turned out exceptionally well. We're very happy together so far. This back and forth process with mixed signals took about 2 years. (that's why in the middle, where i was giving up, i tried to meet more people, hence got a little overlap with prev experience, otherwise, i wouldn't do concurrent process)
Actually it's just a terrible series of misunderstandings and lack of communications. Once we gotten pass the communication stage, everything is a lot smoother for us. Less guessing each other intentions
Girl Age: 31 My Age: 30

Okay. to answer to the main question. The feeling of dating over 30 is:
1. you have to consider the girl's future and time. You need to evaluate if you two are suitable for each other at the shortest time possible (not saying expedite everything.. just that.. for every thing that happened or you two went through, must always ask yourself, "do i want to be with her for long term (50 years)?" If there is no such intention, then give up. Move on. Don't hold her on and continue wasting her youth.This is not the time to take long long time and "try try first".
2. there's a feeling like there's so much to do, but so little time. Like we went local trips 3-4x. and 1 overseas trip. Somehow wish we could go more, but we've only been together for about 1.5 years.
3. Both parties looking for long term, less toxic games, more realistic expectations.
4. both parties stable in career, no funny ideas about throwing money into entertainment along. Everything also hvae long term in mind. (example, not always wish for overseas trip, sometimes stay budget hotel, sometimes stay better hotels. If eat well during this date, then next few dates eat something more frugally)

I'm already planning for proposal and bought ring d. But covid-19 push back my plans (since i plan to propose during a trip)


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