Ready to Mingle

My life took some unexpected turns, and I became single again at the ripe age of 38.

After a period of adjustment, I am once again entering the dating scene, for better or for worse. Though I may now have a clearer idea about what type of woman would be compatible with me for the long run — ideally mature, mommy-like with the right balance of affection and dominance — nevertheless, by no means I am expecting this to be a simple search.

Therefore, I intend to enjoy this process and document my experiences of exploring Sydney, while meeting new people in various social events. I trust God to provide me a second chance at romance in his timing. For now, one thing is for sure: I am ready to mingle!

#1. Speed Dating for Ages 35-55 @ Soultrap Bar

• October 26, 2023 (Thursday)
• 70-72 Campbell Street, Surry Hills 2010
• Hosted by Speed Dating Social

It was a rainy day, a damp start to my journey. I took an Uber to Surry Hills and discovered the entrance and stairs leading down to the Soultrap Bar beside an abandoned retail property.

The cocktail bar itself also wasn’t much to look at. It was cramped and noisy, and given that at least 40 people associated with this event turned up, I knew it was going to be a hectic evening.

I noticed that I stood out a lot too. With my baby face and Asian genetics, most Westerners would think I was underage for the night, not to mention the makeup I had applied, plus my vivid blue hair. However, this suited my search for an older lady interested in a mommy-boy relationship.

After signing in with the organisers, I was placed at table #7 to begin. I chatted to Michelle, a woman working in aviation in her 50s. Several tables later, I had already begun to feel the strain in my voice — the noise of the venue really made everyone frustrated, even the extroverts.

At table #11, I got to take a much-needed break, since one of the ladies didn’t show up. Toward the end of the event, I had spoken to around 18 prospects. For the great majority of them, it was also their first speed dating experience… and perhaps their last, at least with this organiser.

I was mildly attracted to few of the ladies, but none of them displayed the vibe I was seeking after. Regardless, I tried matching up (unsuccessfully) with several just for fun, including a German woman who produces electronic music, a Cantonese divorcée with an ex-husband that turned gay, a funny New Ager with some absurd stories, and a cat lady who plays Pokémon Go and lives in Lane Cove.

The highlight of the evening for me actually came in the form of a 54-year-old Swiss businessman named Markus. We stayed back after most people left and he shared with me about his views on current political affairs, his travels to European nations and their cultures, and his experiences with women of different backgrounds. He spoke highly of Taiwanese girls having the most well-balanced characteristics among all Asian women. I guess I would be inclined to agree.

He left me with sage advice: the easiest place to get a wife is in a country that’s fought a recent war.

#2. Speed Dating for Ages 38-52 @ The Oaks Hotel

• October 31, 2023 (Tuesday)
• 118 Military Road, Neutral Bay 2089
• Hosted by Encounter Dating

Less than a week had passed, and yet I was ready for seconds in my speed dating adventure.

Upon entering The Oaks Hotel in Neutral Bay, it was apparent that the facilities there were markedly nicer than your average underground bar. Along with pubs and restaurants, the entertainment block boasted gaming spaces and function rooms. We even had a terrace to utilise for our event.

Being the first to arrive, I was assigned to table #1. Interestingly, I later recognised a few people from the evening at Soultrap Bar last week. Slightly awkward, but nothing devastating.

Thanks to the improved environment, I enjoyed quality conversations for the most part. Due to this locality, many of the ladies I spoke to also reside around the North Shore area.

So there was a Kiwi woman who talked about female dominance in her culture, though it sounded more like bossy wife behaviour, rather than the firm maternal guidance that I crave. Another Kiwi lass mentioned wanting to learn the cello as a girl, but was forced onto the violin by her controlling mum. Two tables later, I engaged with yet another Kiwi — a mother who had recently deterred her child from playing the cello, but to focus on the violin instead. Strange combos and patterns!

If you noticed the date, it was actually Halloween. There was a Chilean woman present who dressed up as a Mexican skeleton bride. Unlike a bony skeleton, she was a bigger lady — the only one at the event, and so I was excited to meet her. However, her accent was somewhat sharp, and our cultural differences proved a little strong as well. Regardless, she was kind and encouraging.

A funny thing that happened: two of the women went off to play pool during the intermission, never to return to their seats. So in the end, I saw a total of 11 prospects — a good number upon which to conclude the event, just before I started to run on emotional fumes again…

Sadly, I still matched with nobody, not that any of them really tickled my fancy. I realised that among the general population, it remains uncommon for women to seek a younger boy as a partner.

I shall continue my journey, but will attempt to diversify my experiences going forward.

#3. Speed Dating for Ages 27-41 @ Four Hundred Bar & Kitchen

• November 14, 2023 (Tuesday)
• 99/103 Miller Street, North Sydney 2060
• Hosted by Encounter Dating

On the way to this event, I went by North Sydney Boys, my old high school. How time has passed!

It took a little while, but I found the Four Hundred Bar & Kitchen hidden on the rooftop section of Greenwood Plaza. The place is a neat little restaurant that serves pizza and beverages. Upon arrival, organisers Ashley and Belinda recognised me from two weeks ago.

The age range of participants was younger than my two previous experiences. I decided to branch out and not limit myself to a narrow approach. Only God knows who’s out there.

Immediately, I noticed that there were quite a few Asian girls: three from mainland China, two from Hong Kong, and one from South Korea. I was, however, the only boy of East Asian background.

The Korean girl turned out to be a follower of Christ Jesus. She was upfront and open regarding her learning disability, and testified of God’s hand in helping her overcome numerous challenges in life. She was hoping to meet a stable Christian who caters for her condition. In light of my brokenness and special requirements, I can only pray that she is provided such a husband by God’s grace.

It was with the Cantonese girls, Belle and Emily, that I found some future potential — at least within friendship. Belle is one year older than me, and she brought along Emily, who is 29 years young.

Emily seemed like the creative type, with her work revolving around animation, though I do not yet know the details. After expressing my dream of making indie games, she mentioned knowing people who are developers and would be willing to introduce me when the time is right.

She also lives in Newtown, where I have been meaning to visit to shop for some fancy new threads. Perhaps I may have the opportunity to take her to a salon and get our nails done too. We shall see what happens, but in any case, the pair of Cantonese girls became the first matches on my journey.

#4. North Shore Munch for Kinksters @ The Orchard Hotel

• November 25, 2023 (Saturday)
• 455 Victoria Avenue, Chatswood 2067
• Hosted by MissKinkyPeeps (Penny)

It was time to explore a different crowd. I found a kinkster social being held locally at Chatswood, which gave me the perfect opportunity to take baby steps into the community of this subculture.

So I stepped into The Orchard Hotel for the first time ever since arriving in Chatswood in 1996, and there I met Penny, the organiser for the event. She made sure newbies were looked after, which was especially helpful for someone as socially awkward as me in party settings.

I first met several nerdy guys who are into Dungeons & Dragons. I wasn’t nerdy enough to connect with them. But on that table, there was also a law student who told me about sadomasochism court trials, which led me to inquire as to what extent could an individual give legal consent to be abused during a BDSM play session. It was an interesting conversation topic, to say the least.

As I moved on, I was eventually introduced to a girl named Danielle. In her 30s, she is currently in the role of a service slave to John, her master in his mid-60s. John maintains a relationship with another woman a few years his junior called Miyuu, who then makes Danielle’s metamour.

Miyuu is, in fact, the original founder of this munch event in the North Shore area. However, she was diagnosed with cancer and had to take a step back. Danielle is also taking care of Miyuu as part of her service to John. The three of them now share a household together in harmony.

In some ways, I admire the security and commitment of this sort of master-slave dynamic, which parallels a biblical intensity. It correlates with my desire for a romantic authority figure.

#5. Christian Singles Mixer for Ages 26-44 @ Vessel Dining & Bar

• December 12, 2023 (Tuesday)
• 1 Shelley Street, Sydney 2000
• Hosted by Sydney Events TTD

There aren’t many dating socials available for Christians out there, and many people seemed to have jumped onto this one with haste. I only managed to score a spot here after being on the waiting list.

Upon arriving at the restaurant in the CBD, I spoke to the organisers and found out that they aren’t actually believers, but have stepped up to fill a gap in the market. Fair dinkum, I suppose.

The issue was that they hired a matchmaker to give a talk. This particular Asian auntie had a rather weird and annoying personality. They also provided her with no microphone, so half of the time we couldn’t really hear what she was saying anyway. And lastly, my fellow brothers and sisters expected Christian coaching, not some general, mediocre advice delivered poorly.

The speaker’s ramblings also cut into the speed dating portion, so we only got to meet half of the participants of the opposite sex, which felt abrupt and incomplete.

Nevertheless, it wasn’t an entirely fruitless affair. I met a girl from the Chinese province of Yunnan by the name of Ruilin, who became interested in hearing my alternative, faith-related music. She also brought along a friend who does research in 3D printing, so that was something different.

I encountered Jamila as well, someone I met while attending St. Barnabas Broadway earlier this year. It was kind of funny. She asked if whether May would care about my involvement in dating events, and even questioned whether I was seeking a man or a woman. Nothing I haven’t heard before!

Perhaps indicative of divine appointment, I conversed with a Malay girl named Debbie. She told me that she’s part of Grace City Church, a faith community in Waterloo that I have wanted to check out, but just unsure of the right timing… until I met her.

She even attends the evening service, which is the congregation that I would very much like to visit. Interestingly, my journey of mingling has ultimately pointed me back to church once again.

You can’t go wrong when you match with Jesus!

#6. Christian Singles Mixer for Ages 45-65 @ Sanctuary Hotel

• January 10, 2024 (Wednesday)
• 545 Kent Street, Sydney 2000
• Hosted by Sydney Events TTD

The year is new, and I thought I’d go for a bonus round before settling deeper into my new church.

Picking up where I left off previously, I decided to check out another Christian social — this time, however, arranged for an age group beyond me. So how did I sneak into this mixer, you ask?

I bookmarked this event earlier on and soon noticed that tickets for guys were at a 50% discount, obviously due to the fact that there are far less single mature men than women in the church.

A short while later, those same tickets became free. I knew that they were desperate to fill numbers, and hence seized the opportunity to reserve a spot. When I arrived at Sanctuary Hotel on this date, the organisers were happy to let me join, even though I was underaged for the evening.

The people who attended were indeed over the hill, some more so than others. During introductory activities, I sat next to a senior man who had trouble hearing and understanding basic instructions. At another table, an elderly, overweight lady with a bad leg couldn’t get up to her stool, so she was given a special chair. It was kind of depressing, and I felt bad for them.

On a brighter note, the dating coach Cristina Davy who spoke to us was a way better presenter than that matchmaker they had last month. I got to chat with her later too, and she taught me a thing or two regarding masculine and feminine energy, as well as recommended me to go to art events for meeting people, especially mature women who may be more inclined to date younger guys.

I also talked to a woman called Margaret. She wasn’t keen on revealing her age, but my guess would be somewhere in her mid-50s. Despite being a grandma, she showed a youthful, cheeky disposition.

Previously, she dated a Catholic man for a full decade, but it went nowhere, since his faith was dead. Now, she hopes to find someone with a true heart, and I wish her all the best.

As for yours truly, I trust God to continue guiding my steps and lift me up to new heights when the timing is right, according to his infinite wisdom.