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Cindy Leong, Chief Dating Coach of Divine Connect.
Over a thousand Singaporean singles took part in a personality test conducted by local psychology-trained Enneagram practitioner and matchmaker agency Divine Connect. They are the first in Asia to use the Enneagram roadmap to study and help singles discover themselves.

The roadmap states that we are primarily made up of nine core personality types. “Ennea” means nine in Greek and “gram” means points. The Enneagram is essentially a tool with nine points. Each type contains its own unique traits. It is what determines how an individual think, feel and behave on ‘autopilot’ mode. It is also what determines why an individual may get ‘stuck’ in his or her defence mechanism, often finding it hard to get out.

“Why some people remain unable to find love is because of certain traits in their personality,” explained Cindy Leong, Chief Dating Coach of Divine Connect.

“Discovering and understanding the common blind spots in different personality types can drastically improve one’s chances of finding love. It is all about learning and gaining self-mastery through self-awareness and compassion,” she added.

Type One – The Perfectionist

According to the Enneagram, the Type Ones are most associated with standards, systems and rules. They are the strong self-critics, adept at finding fault with things and finding it hard to let go. People may find it hard to get along with them. Because of their high standards and expectations, they may even find it hard to get along with themselves.

“These are probably also the top factors why they remain unable to find love,” said Cindy. 

“They tend to get angry over things they cannot do anything about. After that, they get angry with themselves for being angry. When it comes to dating, it is quite impossible to find the person that could please them. Or they want the person to be acting, thinking, behaving the same way as them. There can be a lot of self-blame. They may come across as critics. When that happens, it is very hard for this personality type to emit positive energies. It just pushes people away.”

“The key for them,” Cindy continued, “as with the other types, is to gain self-mastery over their own personality, learning when to let go and let their hair down, and allowing themselves to see the good in every experience.”

 

Type Two – The Helper

Type Twos tend to be too nice and compensating, often at their own expense. They are friendly and warm, sometimes too eager and quick to help. As such, they are inclined to be attracted to people who need assistance.

“Sometimes the question becomes, is the Type Two guy attracted to the girl because of her qualities or the fact that she needs help?” said Cindy.

“If they fall in love because they are needed, this is usually not a healthy relationship to be in.”

The Helpers get their sense of worth primarily from helping others. They seek validation or affirmation from people they’ve helped. It makes them feel useful and needed. They tend to attract people who come to them for the wrong reasons, because they are too quick to offer resources. Often, they will be taken advantage of and surrounded by people who are not sincere with them.

“Many Twos get hurt partially also because they have allowed themselves to be treated this way,” said Cindy.

“Building their self-worth through coaching on self-identity and assertions may serve them a long way.”

Type Three – The Performer / Achiever

Type Threes are the typical performers in a sales team. They may come across as cold blooded and vain. They are task oriented and will do whatever it takes to achieve their goals. When it comes to relationships, it is a task. They tend to hide behind a mask of success; the need to look good, the need to comply with a certain image; there is a possibility that they wish for their partners to conform to a particular image as well. They tend to enjoy trophy partners, some heavily dependent on the look good factor. Because of this façade of work, success etcetera, they forget who they truly are; basically losing themselves. Many times they may go through mid-life crisis, realising that what they have been seeking is not what they truly desire after all. Their weakness is primarily not being able to be vulnerable, to be truthful to their own feelings. They may also come across as being too good to be true.

“A Type Three’s partner may get overwhelmed by the Achiever’s need to maintain a perfect image. They may find Threes very hard to grasp and too mechanical when it comes to emotions,” said Cindy.

Type Four – The Romanticist / Idealist

They are the artistic people. They get to the heart of the matter and are very empathetic people. Usually they can be found in the art and creative scenes.

“In relationships, they tend to have this ‘push-pull’ pattern,” said Cindy.

“They see something they want, they ‘pull’. After achieving it, however, they realise it isn’t as good as they thought it to be, so they ‘push’. After a while of ‘pushing,’ they may feel a sense of abandonment or distancing, again they start to ‘pull’, repeating the cycle.  They play what I call the ‘push-pull’ game.”

“Because they do not want to be rejected, they reject others before they can get rejected. It can be quite a complicating mechanism.”

“Until they gain self-mastery of this aspect and their many layers of emotions, it is hard to get into a lasting relationship,” continued Cindy.

Type Fours may find that people are not able to match up to their emotional intensity, or get frustrated over a lack of space to express their emotions. Others, on the other hand, may find them overly emotional and difficult to understand. They are, statistically proven, the most prone to depression among the nine types. They can be quite sensitive, emitting negative energies and letting emotions get the better of them.

“Especially in Singapore, they tend to be easily misunderstood where the culture is not as accommodating for Type Fours,” said Cindy.

Type Five – The Observer / Investigator

They are the ones who prefer to be behind the scene. They like analysing things and amassing huge amounts of knowledge. They usually make good philosophers and inventors like Thomas Edison. The downside to this personality type is that they tend to remain as an observer – risk-averse, over-thinking, and analysing and therefore neglecting concrete action.

“For example, a type five wants to learn swimming. He watches a video about swimming. He reads books about swimming. He stands by the pool observing the swimmers and comes up with a dozen theories about swimming. In the end, he doesn’t jump into the pool and actually learn how to swim,” said Cindy.

“Same thing for relationships and love.”

The type five may approach relationships in very logical ways, but they never tap into their emotions, sometimes even coming off as cold, detached and distant. They sometimes think of emotions as obstacles to logic. They are the most detached of the nine types, preferring to withdraw into their own private space and privacy. Because of their strong need for personal space and freedom, even allowing one person into their ‘circle’ will require tremendous amounts of trust, time and effort.

“A lot of handsome, highly intelligent and eligible singles are Type Five,” said Cindy.

“Until they learn to be in touch with their emotions and to open up and take risks, getting into any intimate relationship may be seemingly too ‘intrusive’ for their ‘comfort.’”

Type Six – The Loyalist

They can be very loyal people, but also sceptical ones. They like to be followers, to conform to a leader, a vision. They feel comfortable following a good leader. But anytime the leader shows signs of deteriorating, the loyalist is usually the first to leave. There can be a lot of distrust. It’s a love-hate relationship regarding authority and trusting people in general.

“Trust is always an issue for Type Sixes. It’s either they totally trust or not trust at all. Sometimes they segment their trust. People need to earn their trust,” said Cindy.

“They usually doubt the obvious, and if things are too good to be true, they question if there’s any agenda or motives. When it comes to an intimate relationship, it takes them a long time to trust the partner, or to even say ‘I love you’.”

In Enneagram, there is also the subject on ‘wings’. They refer to the second dominant personality type beside the core type. A person may be a Type Six with Five wing, meaning that he’s a Six at core with Five as secondary.

“A lot of Type Six people with wing Five or vice versa are very difficult in relationships. They doubt, they over think, they distrust – sometimes even distrusting and having a lack of faith in themselves,” said Cindy.

Type Seven – The Enthusiast    

They are the adventurous ones; the ones who enjoy trying new things. They are the typical party animal.

“Usually you can hear them before you see them. Having said that, there are introverted Type Sevens too,” said Cindy.

Very bubbly and energetic – the downside to this personality type is often difficulty in following through with their ideas, even though they have a lot of ideas. In short, they don’t see things to completion. Even though they may find it easy to attract people they like because of their bubbly personality, it is hard for them to commit.

“They are also sometimes what I call the ‘options maximizers,’ said Cindy.

“They want plenty of options. They want to keep their options open. Their dominant thought is always ‘what if there is someone better?’ They usually have commitment phobia. This may sound ‘extreme’ but they prefer options more than the other Types. Too many balls to juggle and nothing gets done.”

Type Sevens can be very social, yet they are fearful of getting a committed relationship or partner, because any form of commitment is a limitation of choice. When they get too close to someone, they may be afraid of letting the other party see the real them.

They also feel the need to keep up their social, hyper and joyful front. Exposing their sadness to others actually causes others to not take them too seriously, so they rather suppress this other side of them. To find someone who can accept the downside of Sevens thus becomes a challenge.

They are generally positive people, so much so that any problem is no problem at all. They prefer to sweep things under the carpet. They don’t see the seriousness of actual problems in relationships. Usually a person has to throw a tantrum or give an ultimatum to garner their attention.

“Unless a Seven takes up the difficult task to have themselves settled and grounded, staying in a committed relationship can be a constant challenge,” said Cindy.

Type Eight – The Challenger    

They are the assertive, masculine and outwardly strong ones. For the ladies, that could be a problem.            

“Mr Lee Kuan Yew is a typical Type Eight – assertive and can be very intense and extreme,” said Cindy.

It is safe to say that most guys do not prefer ladies with this personality type as partners. These ladies tend to attract weaker guys, yet those are usually furthest away from their ideals. They want stronger guys, but there’s often no good reason why stronger guys would be attracted to them. This is a typical example of a mismatch of expectations.

“Sometimes I even have to coach ladies on exuberating feminine energy to get them to soften up,” said Cindy.

“For them to effectively get into a relationship, they need to understand that it’s okay to be vulnerable at times. As much as they don’t like to expose their vulnerabilities, preferring to hide behind their powerful front, they need to learn how to connect with another person simply by being in touch with their vulnerable self.”

A Type Eight often gets angry, but it may really be just the top most layer. Beneath it is a host of other emotions. It could be frustration, sadness, disappointment or even insecurity. They may not say it, but rather manifest it as anger.

“Many times people simply take them as ‘angry birds,’ quite hard to even get close, and needless to say, getting intimate,” said Cindy.

“For Type Eight guys,’ she continued, “they may come across as being too aggressive. Some ladies may not like it – too direct, lack of sweetness. So if they do not know how to sugar-coat their words, or filter their thoughts before speaking, this may cause significant tensions in a relationship.”

This personality type, being impatient and quick to judge, also tend to delete people they dislike from their lives very quickly. This makes it even more challenging to build close relationships.

“Until Type Eights learn to have mercy and faith in others, it can be hard for them to open up to a brand new individual,” said Cindy.

Type 9 – The Peacemaker

The Type Nines are the easiest going ones.

“Maybe too easy going,” said Cindy, “so they go along to get along.”

They become void of their own directions and opinions, often taking on the group agenda as their own. People tend to find this personality type too monotonous and boring. This is the number one reason why this group of people are left on the shelf. There are almost no outstanding qualities that makes a Type Nine stands out.

“When you ask them to tell you something interesting about them, they will typically answer things like ‘nothing much, just sleeping, eating, watch tv etc,” said Cindy.

Many times he’s the typical Mr. Nice Guy – the guy who gets ‘friend zoned’. The guy whom girls like to hang out with for company but not get into a long term relationship with. It is very hard to dislike a Type Nine, but it’s also very hard to love this personality type, at least at first, because of a lack of outstanding qualities or individualism.

“They prefer to withdraw from conflict,” continued Cindy, “unlike Type Five who withdraw to think.”

They tend to give off the impression that they are unclear of what they want, lack assertiveness, ambition and clarity. This is a problem especially for guys as masculine energy and ambition are strong factors for attraction.

In some cases, they tend to get attached with anyone who comes along and accept. Even if it is the wrong relationship to be in, they will not leave, because leaving may cause conflict and they not like such conflicts.

“In Singapore, there are a lot of Type Nines, both males and females, primarily because of our culture and structure,” concluded Cindy.

“Many grew up to be sheltered and lack a mind of their own. Unless Type Nines decide to stop ‘sleep walking’ and wake up to a sense of direction, it may be challenging for them to be attractive.”

What the personality tests say

“The test can say a lot about a person’s personality, and it is important to make sure that this information works to one’s advantage.”

“Coming face to face with one’s vulnerabilities and weaknesses, as I mentioned, is not to discourage or create despair. On the contrary, it is meant to help one become aware and thus improve and grow as a person,” said Cindy.

Pic: Cindy in one of her radio talks. 

“Only by knowing yourself, gaining high self-mastery of yourself and being sincere in trying to relate to others can you truly improve the quality of your relationships.”

To find out more about Cindy, Divine Connect and the enneagram profiling test, visit https://www.divineconnect.com.sg/.

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