Dating lessons I wished I'd learned in my twenties

As someone who struggled with self worth and abandonment issues as a kid, I developed a Great Wall as a shield for myself. Because I was bullied and had friends who left me for being neurodivergent, I was deeply afraid of having someone leave me if I chose to open up about myself. I shut myself off of forging any relationship in high school and at uni. Conversely, I was scared of leaving someone behind whenever I moved cities. Rather than getting deep, I would stay at the surface. While I’ve torn 75 percent of my Great Wall down, I am still learning how to get vulnerable.

Falling in love with the idea of someone is always easier than falling in love with the reality of who someone is. As an idealist, I wore rose-tinted glasses that drowned me in a rosé haze of utopia. I never looked at the red flags nor did I bother to care about one’s flaws. When the imperfections popped up in front of my face, it was a rude awakening that pulled the rug under my feet. Nowadays, I realise that Prince Charming is human, too. Rather than seek perfection, I seek authenticity, trust, accountability and strong communication. But, if a guy has too many red flags, ciao.

In my early 20s, I was a sucker for a celebrity lookalike. My go-to pickup line and/or compliment would be like: “You look like (insert celebrity name here)”. As superficial as this sounds, I always felt that having a civilian celeb lookalike was the next best thing to the real deal as A-listers were out of my league.

However, in my late 20s, a different type of attraction sank in. After dating for so many years and honing in on my preferences, I know choose to pursue men who are family-oriented, ambitious, creative, independent, emotionally intelligent, open-minded, humorous, charismatic and non-conforming to society’s standards (i.e. taking up non-corporate jobs or styling themselves unconventionally).

My number one question to every prospective suitor was “What’s your sign?”. It was a dealbreaker for me if a guy wasn’t a Leo, Aries, Sagittarius or Libra as every astrology site says that I, a Gemini, should date those signs. Rather than try to suss out one’s entire natal chart, I decided to throw all caution to the wind and not limit myself. Turns out, out of all the signs, I have stronger relatability, communication and openness with Taurus and Cancer men (I guess I can attribute that to my Taurus dad and Cancer mom making me attracted to both signs!), signs that I would have originally turned down!

Am I needy? Yes. Do I have a bad case of abandonment issues? Heck yeah. Since I had a history of being ghosted by former prospective suitors, I spin into an overthinking and triple texting spiral if someone doesn't respond to me. I assumed that not replying to my messages was intentional ghosting when that’s so not the case in reality after I get my replies. Little did I know that I projected my trauma of being ghosted until someone pointed out to me.

I used to think that men would be attracted to me because of how I looked and I exploited my looks to bring all eyes on me. When I reinstalled Hinge last year, I uploaded a photo of myself with “bleached” eyebrows. I thought that men would be turned off by it, but my expectations were proven wrong when I had close to 30 suitors like that pic. I asked one guy why he liked it and he said that he was attracted to my confidence to go browless. That was a wake-up call for me because I never knew that the confidence I had to be different was also beautiful, too.

A paraphrase of one of the most misunderstood quotes spoken in the Netflix dating reality "social experiment" Love is Blind, having that emotional and mental safety are priorities I put first before I choose to kiss a partner. Though I had moments where I compromised my comfort to please someone else, I am fortunate that most men respect my decision to place my boundaries first.

I was told that being too bold was a turn off. I know that I am wired to have a strong personality, yet that shouldn’t make me fine-tune myself to appease others when I forcibly tone down my loudness. Being an unfiltered person is a lot for someone to take in, but that asset pays off whenever I mix puns with PG-13 compliments that express my interest directly. Remember: there is no right or wrong answer with how you want to approach people even if you are timid!

From the talking stage to the official stage, you don’t need one month of talking to get to the casual stage nor do you need five months to become IG official. In between those stages, you can explore an FWB relationship in the talking stage and/or play the field before you narrow down your options. A former commitment-phobe, I have never gone anywhere past three months in a talking stage. Nowadays, I’m more open to trying things out longer than that. Learning to pace myself is a struggle, but it’s something I am learning to harness as I am impatient. Having an expectation-free timeline has helped me to not compare myself with my married friends or cousins who are in serious relationships.

At the start of covid, I matched with Zane* (not real name), a British expat, on Hinge. After a few weeks of texting, he ghosted me after our attempts to meet up for dinner fell through. Then, we matched again two years later. I pulled up my WhatsApp history and texted him. We talked on the phone for 15 minutes, but felt zero sparks. We tried to make plans, but it never materialised again. If something didn’t work the first time and he didn’t put in the effort to build something with you twice, let that be a reminder that not everything is meant to be fixed.

Dating experts are not a fan of situationships, but I think that there is always a silver lining underneath it all. Since you’re technically single with some strings attached, situationships give me room to learn more about myself before taking things further. In every situationship, I discover what my love languages are, sharpen my red flag radar and set a goal for the type of relationship I want (for the moment). While developing feelings are an essential core to building a relationship, situationships allow me to warm up to someone’s vibe before I sink my boots into the mud or check out. Though most situationships are temporary, it helps to figure out your wants/needs in the long run.

In the past, I've fallen for well-tempered men who charmed me with their words, soothed me with their laughter and pampered me on dates. However, the gentleness was a cover for something more sinister. Between being blindsided by a last-minute hook-up proposition to finding out that a Hinge date had a girlfriend from IG Stories, both situations made me realise that people are good at hiding their worst selves underneath the guise of niceness.

Looks do matter to some degree, but chemistry, similar interests and values are what attract you to someone. In fact, having no fire between you and a potential date happens more frequently than you can imagine. I've lost count of how many times this happened to me despite finding the guy conventionally attractive. Even though I feel guilty about this, I have to remind myself that it is normal to not be attracted to them.

I went on a date with a 29-year-old aspiring filmmaker when I was 22. Conversely, I've also gone on a date with a 20-year-old Berklee college student when I was 29. From 23 to 26, I started going on dates with guys my age to a year older with the exception of a 33-year-old when I was 24. At 27, I talked to 40-year-olds on Hinge. For the past two years, I have gone on dates with younger men that were 27 to 21. Between 20 to 40, the men I went on dates with couldn’t care less how old I actually was. The big thing I felt was that the different stages of life could make or break a relationship. Whether it was a student or C-suite bachelor, different mentalities within those age brackets could be felt in our interactions. Now, I prefer to date men between their mid 20s to mid 30s as we are at that stage of trying to figure ourselves out and still going through life changes.