Before you ask me what credentials I have to be writing this essay, first off—I don’t have any, but I did leave that chapter of my life abroad in Singapore once I hit 29 (or was it 30) with the intent on coming back to the states to find a partner. Also I’m not even using AI writing tools, just word blabbing so there you have it.
I’m Taiwanese American, born and raised in California who has had the privileges of going to Taiwan, China, and Singapore for study and work abroad on various occasions. Pros is that I got to also travel and see the world, live a meaningful life to me, but spent the majority of my 20s trying and rushing to figure things out in my career, without much focus on dating and love prospects (which I wish I did more of). Cons is that I didn’t know how to date nor how to go about being in a relationship because I had limited experiences.
I had the career, work experience, and greying hair of a 40 year old, but I had the emotional capacity and regulation of a 15 year old nearing puberty because I didn't date enough when I was younger and had no flipping clue what I was looking for in a partner.
In early stages of dating, I was adamant about always having my way, and would immediately cut people off if they didn’t fit the criteria or they made a mistake—that was my fault honestly, as I now realise being in a partnership is always about compromise, accepting imperfections without judgement, and growing together. I didn’t know myself well, and I started the dating journey painfully in my late 20s and early 30s.
I had been in my Girl Boss phase for most of my life, and I gracefully acknowledge that I had a wonderful (but sometimes stressful) life. But after all said and done, I felt like I hit a wall face-on, and was left wondering, “What life am I building? And is the life even meaningful to me? And what would it look like if I built it with someone I loved?”
That realization sunk in, and it was time to buckle down and be intentional about finding my partner.
You Become the Outsider Looking In
Once I hit 30, I felt lonely, and not in the “I have no friends” type of lonely, but that I had all these wonderful experiences and I had no one to share it with. It was funny because I was constantly surrounded by people through my work, making new connections and friendships through my community, and feeling more than connected than ever via the interwebs but I felt like there was something lacking. All various points of contact, but perhaps shallow when I craved depth.
I wanted to build a life with someone, to come home to, and to share my deepest internal secrets and thoughts I never lay bare to others.
Perhaps I was still chugging along as the same person, but everyone around me in my sphere was evolving with their partner and life; there were huge milestones, like having weddings, raising children, buying homes, and doing all the things that really rooted you and gave meaning to their lives. I wasn’t jealous, but a bit sad, maybe like I felt like an outsider looking into the world they were building. The birthdays, the holidays, the intimate family events that were just among their unit–these things were always welcoming, but felt like I was not a core part of it.
Adios Singapore, Hello San Francisco
Anyways, after a good stint of 3 years in Singapore, I left that small dating pool and decided to come back to San Francisco Bay Area for work progression and to intentionally find a dating partner. The people in this Bay Area pool were intelligent, and most likely had good backgrounds that I was looking for in a partner. Also, the pool was a lot larger here, with people similar to my backgrounds as Asian Americans. I also wanted to start earlier than later; I preferred not to start dating in my mid-30s or 40s as I felt like it progressively got harder as I got older. Why? Because the pool gets more limited, your personal views on life get stronger and inflexible, and I preferred not to date younger.
While living in San Francisco, you had the entire Bay Area to date around and that is to your advantage. Complain about SF all you want, but you have some of the smartest people here and it’s international so you have folks of all walks of background coming through.
I had mostly used Hinge and Coffee Meets Bagel, meeting people for coffee and walks as a quick way to meet new people. It was like a numbers game, but I soon picked up how to identify red flags, and what were promising factors. Here are a few that I’ve noticed, and you can see how they are upon initial meetings. A lot will share how they will be in the future, including planning capabilities—if he can’t plan a date, how is he going to plan a whole ass life with you?
Green Flags
- strong moral compass and values to be a good human
- similar humor and lifestyle
- pays for the first date out of goodwill and care
- good planning capabilities and responsiveness
- likes animals, has sisters, and is an uncle already
Red Flags
- reckless driving and getting angry at minor things
- wishy washy, non-committal, and not giving straight answers on the future
- ghosting and then reappearing when convenient for him
- many girl friends in his photos, like why would you add that?
For future reference, if someone states on their dating profile: “looking for long term, open to short term,” do not date this person. He most likely doesn’t know what he wants still, as it’s like..sure, I’ll settle for the right person, but I’ll fuck around and have fun while stringing along girls until I realize they’re not the one.
Dating in your 30s Suuuuuuuuuuuck
If you notice that dating becomes harder in your 30s, trust me—you’re not the only one. It’s comical really, you suddenly are in your next decade and you realise you’re not as hot as you once were. Sometimes I felt like I wasn’t as joyful or energetic as before, maybe I just got more jaded over the years.
Men in their 40s and 30s can always date down, and maybe they prefer dating a girl in their mid to late 20s. Most women want to date up, as they want someone who is aligned on their timeline if they want to settle, have kids, and do more. It is a lot harder to date a young 28 year old male while you’re wanting to pop out babies, and he’s still figuring out his career moves. It’s not a complete deal breaker, but I found that dating 2-5 years older is ideal.
When I was single, I wasn't sure if I wanted kids because I didn't have a partner who I felt like I could build that life with. So if I didn't know, I needed to figure that out, and that is the shitty case of a ticking time bomb as a 30-something year old woman. I know technology is advancing and women can have children at a later age, but I'd like to minimize the chances that something goes wrong. I hear too many stories of complications, miscarriages, and certain disorders. This is just my own thinking.
What has also been helpful is defining your boundaries, and standing by them. To stand by your values and boundaries, that is respecting yourself. When you respect yourself, others will respect you. The boundaries of what you want should be realistic though, and not materialistic, like he needs to be 6 feet tall.
For example, I wouldn’t date anyone who smoked. I wouldn’t date anyone who was wishy washy, wouldn’t commit or plan dates. If he asked to hang out last minute, I’d say no because I have other plans and I hate last minute planning. Once these boundaries were crossed, I knew this guy was not for me and so I wouldn’t even waste my time.
I tell my girlfriends to find the 33-36 year olds who most likely have stable careers, built a strong nest egg, hopefully did the emotional work, and are ready to settle down after exploring and having fun in their 20s.
I suspect it’s because women in their 30s have gotten to a point where they’ve narrowed down what they want (more or less), and are quite set on it.
I Found The One!
And out of nowhere, I found him. On a random whim, I was looking at previous convos with people I connected with while I was in Asia, and I re-messaged my current fiance. I had actually wanted to see who I spoke to previously, and remembered he played tennis. Over the topic of tennis, I asked if he was still around and playing; we then met up for drinks and the rest was history. We now play tennis together, and my father got us into pickleball.
The whole thing of dating almost took me a year and a half, a whole lot of terrible and some good dates, and defeating this nagging voice in the back of my head that something was wrong with me, or that I’d end up alone. It’s sometimes like job searching, where you’re in this weird black abyss with no certainty of the end. No certainty of finding a partner.
Though the weirdest thing that happened was when I started enjoying being by myself and being self assured, that was when I actually met my partner.
I didn’t come perfect to him, and he didn’t come perfect to me. But by focusing on the important things, like similar values, lifestyle, dreams, and life philosophies, he was perfect for me to work and build a life together. Plus, no one has ever made me laugh like he has; we have the same silly humor.
Advice to my Single Ladies Out There
Like my dad always says, “You should have 5 guy friends when you are dating.”
It sounds more serious in Chinese, but he’s always told me to date around as much as possible before settling down. And putting all your eggs in one basket is dumb, hence why you need 4 other friends. Given the realities of online dating, I would recommend the same unless both of you have agreed on exclusivity. If he is not ready, then it’s a way of him telling you he’s not ready to commit to you and is looking if something better comes along. At that point, keep dating until you find someone who is.
All in all, dating is a rollercoaster. I know it gets exhausting after all this time, but once you reach the end, the craziness of it all is worth it.
If You’re a Man and Reading This for Some Reason, and Got This Far…
Here’s my advice to you. Women (even independent women) want to be seen, taken care of, appreciated, and given space to breathe while you take the mental load off her. Figure out her love languages, and what she truly values. If she doesn’t love flowers, but would kill for a kouign amann at Arsicault, get her that instead.
I feel that men are too soft these days, and soft, meaning there’s a lack of proactivity and initiative. It gives women the ick. You cannot expect women to do everything if you expect her to also have a career. If you have money, you can have a traditional wife. But if you’re broke, you can’t be expecting tradwife privileges without tradwife money.
I feel that women are too strong these days, and pushes ahead like “I don’t need a man, I got myself” mentality. That’s fine until it gets toxic and isolating. I admit I was the same, but now have slowly unlearned a lot as my fiance has given me the space to soothe my nervous system and relearn how to like bright colors again.
