Curious about the changing dating scene, Cultivate had breakfast with a group of men and women – young and single – to hear how they’ve been dating, or not. These at the ‘table’ were seated with a marriage counsellor, Dr Liang Wei, and moderated by Ariel, the Cultivate Chairperson. Others from different life-stages also turned up for the exchange on dating and marriage perspectives, relationship woes, and challenges faced.     

We had earlier found that men are still keen on marriage – significantly more so than their female peers, which sparked off many conversations on differing dating trends, along the lines of age and gender.   

We had some introductions. Single and in his late 20s, Xavier* shared how he was initially unable to progress beyond a few dates. Starting out with a more laidback approach, he had shifted to actively approaching others and taking more initiative after hearing from female friends and dates that they found a lot of males too “passive”. This set him on a path of reading and discovering more about the gender divide and roles. He encouraged other guys to “be the one to ask the girl out,” and is now seeing someone exclusively.    

Owen* disagreed; to him, gender roles or differences didn’t really matter, whether in the dating scene or at home, sharing how he was “mostly raised by women in [his] family.” He was back in the dating scene after two committed relationships and a ‘situationship.’  

Chloe* shared that she was in her 30s and had actively dated but is now “not actively looking”. While she is enjoying her life as it is, she has hopes to get married in the future. Ben*, single and in his 20s, shared about how easy it was to meet potential partners on apps, but that connections “can be quite shaky.” He experienced a breakup after moving too fast with someone he’d met on-app, emphasising his lesson of not rushing relationships “when fundamental issues have not been agreed on”. He also commented on how some of his dates seemed to have “idealistic expectations” of relationships, and noted how difficult it was to meet people outside of work, while dating a co-worker came with its own set of problems.  

Amanda*, in her twenties and months-fresh to the dating landscape, said she started thinking of it after realising how she wanted to re-prioritise her life. “We work hard towards our career goals, so why don’t we put in the same effort for our marriage or life goals?”  

Others who joined us included mothers with their own vintage dating experiences: one under the guidance of the then Social Dating Unit (involving physical newsletters, ticking boxes of ideals, and snail-mailing responses). She matched with her first boyfriend-turned-husband, one of the heartfelt stories we don’t hear much of anymore. Others in the crowd shared how they’d already settled on singlehood for life and were just interested in forming good friendships.    

A friendly debate began when another woman, engaged in her 20s, shared about how she started her dates efficiently. The first few dates were for laying out values and life goals to establish common ground before moving forward: “What do you want, what are you looking for? Let’s not waste time. I want to have children, so it was a dealbreaker for me. These are easy things, so once you lay it out, you can move past it.”.  

Some in the crowd nodded in agreement, as others, now married with children, shared how they had taken a similar approach after failed relationships. However, the three young men at the table disagreed, citing that they’d scared their dates away when they were too straightforward and the need to be “more measured” when getting to know a stranger.  

Owen in particular, said it felt like treating the other person as “a means to the life you want”. He shared how he might be reacting to his parents’ divorce after their initial functional approach to marriage and diverging expectations in the later years. “It’s kind of like, do you really love me, or do you just need a place for your love to occupy?”  

Our counsellor with years of speaking with couples and singles then weighed in on the current trends he’d seen and reactions to the conversation, calling out the emphasis on emotional sensitivity. “There’s a lot of focus on emotional sensitivity – young men now can be very emotionally attuned to girls, but there isn’t enough focus on emotional maturity. If a man is emotionally attuned but not emotionally mature, he can manipulate you.” 

He also cautioned against clarity on life goals being read as emotional maturity, with young women “anxious to get everything they want in their lives done all at once,” without the emotional maturity to “stretch out all their goals over time.” For example, some youths might hear their mothers or older women carrying bitterness from feeling they have set aside their personal life goals to take care of children and it’s no wonder younger people, especially women, seem more averse to having children. Instead, it helps to take the perspective where “you don’t have to have everything at the same time.”    

Some values he’d seen in thriving relationships were “liveable, loveable, and sustainable”.  

Liveability – What can we live with when it comes to our partner’s qualities? If there was already a struggle with their best side, there would be issues down the road, beyond the expected problems in relationships.  

The types of problems also differ, with some growing over time as others diminish, i.e. two professionals at the start of their careers would have financial problems decreasing over time, while a mismatch in life goals would grow into bigger problems over time, requiring more capacity to handle.   

Loveability: With all our imperfections, people have to “choose who you want to love and grow in the capacity to execute that choice.” This desire to sustain a choice is a protective feature against affairs despite having the ripe conditions, e.g. travelling alone overseas, removed from the familiarity of home.    

Sustainability: Women seemed to be more attracted to emotionally sensitive men. He’s a “safe space I’ve always been longing for” or “I feel like I can share everything with him.” While that is important, it’s also essential to question whether such a foundation is sustainable in the long term, especially since the world is unsafe. Eventually if they were to have kids, they would have to nurture them in this unstable, dynamic, unsafe environment. They would need the emotional maturity to handle it, and grow beyond any immaturity in accepting input only when it suits their feelings and preferences. Emotional maturity is being humble and willing to “confront the gaps and holes in their own lives.” Beyond sensitivity, “we should look for people who give us a sense that as long as the quality of input is high, they will be able to accept it even if it comes in a difficult form.”    

As for morality: “If you live with a spouse who’s always cheating everyone else, it makes you feel insecure. When life takes a downturn, that same skillset might very well be used against you. Some degree of morality is necessary because morality sustains love.”  

The breakfast closed with an exchange on the unequal dating landscape, with a mismatch of expectations that men should be earning an income equal to or more than them i.e. hypergamy. Chloe asked (tongue-in-cheek) “Why should I lower our current standard of living just to be with you if you can’t even bring me to HaiDiLao on occasion?”  

She made an exception for those working for the greater good, such as in counselling or social work. Ben agreed, as this checked out in his dating experience, citing it as a challenge for young men just starting out in their career.    

Building on Chloe’s point, Dr Liang Wei said that money did have value, including providing a sense of safety especially during difficult times where it becomes “a powerful cushion.” When navigating divorce, the more well-off tend to “feel better.”  

However, even if a man is not able to provide a certain financial margin for his partner, the feelings of safety can be provided in other ways. For relationships with significant disparities in income, human connections, wider perspectives, and problem-solving processes would also be divergent. It would then be important to question, “Am I growing my perspectives and my problem-solving approaches in tandem with my partner / spouse? Am I still able to bring different perspectives that will be valuable?”  

For example, a counsellor may earn less than his partner in the corporate world, but might be able to relate to children better. A couple in such a relationship may ask if there is a way of separating their roles such that they play to their strengths. In terms of providing solutions and perspectives, couples “need to be able to maintain that parity in non-SES ways”. A relationship, or a marriage, would then have greater “survivability”.  

He ended with encouraging those who were looking to ask “whether the sum of the parts is able to punch above their weight.” Individual characteristics do matter, but what sustains a marriage is “the ability of two people to come together.”  

We hope you enjoyed reading this update on our Cultivate Commune conducted on 8 March 2025.  

Sign up for our next Commune in May, with a special focus on unlikely motherhood.