7 Types of Guys Who Screw Up The 1st Date


“The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn. ” – Alvin Toffler  


The First Date was supposed to be like what we saw on TV dramas or movies – a curious amalgam of feelings including ambiguity, tension and excitement.

Boy takes Girl out for a wonderful, fantastic time:

  1. Romantic dinner in Savoy
  2. Nice long stroll along the riverside
  3. Small awkward silences coupled with bashful, reserved laughter (from the woman)
  4. Minor ‘electric shocks’ as Boy pulls Girl away from the path of a crazy random cyclist and they both lock gazes at each other, arms interlocked.


But it wasn’t ALWAYS like that, wasn’t it? I’ve been on some First Dates in the distant past and had screwed them up. Never saw the Second Date and got ‘friend-zoned’.

That feeling is worse than the day when I was conscripted into the Army. No Kidding. (‘Bro’ hug to whoever out there who has shared my pain)

I’m sure many of us guys have had such days, though we deal with it differently:

  • Some wait passively for the ONE woman to fall from the sky to magically transform their love lives. Passively.
  • Some go on a frenzy and spam messages on Internet dating sites to almost every single woman.
  • Another decides to ‘give up’ on romance and proclaims to the world that he’s gonna focus on his career instead.

I have since, painstakingly compiled pearls of dating wisdom and point of views from some family members, friends and colleagues (both males and females) over the years.

Today, I wish to humbly share some of the key personas of guys that will probably won’t earn them many Second Dates.

Admittedly, I adopted a couple of these personas in the past with some regret. But luckily I changed my mentality, unlearned some bad traits and learned new ones, which finally led me to my relationship.


1) Mr Universe (the whole world is about him)


Anything and everything revolves around this guy. He talks about himself, and then more about himself. His successes. His interests. His life.

Occasionally, he responds a little about the topic that the girl is currently on and uses that topic to steer the conversation back to himself. Self-absorbency in the highest form.

Ain’t sure if he should just talk to the mirror or whether he might notice if the girl slips away under his nose during the Date.


Mr Universe: “My work is tough. I have to handle many really difficult clients but all of them just don’t understand that I require time to accede to their extra requests and reports.”

Girl: “Oh yes I totally understand you, man! Worst thing for me is, my boss dosen’t really give a crap. He still expects me to take it and be passionate all the time…”

Mr Universe (interrupts): “OMG! Don’t get me started about my boss. My boss is… etc. etc. etc.”

Girl: “Oh …”

Mr Universe (continues): “Etc. etc. etc.”


2) Mr Smart-Ass


This guy really knows it all. From how the Universe was created to how the world’s most powerful politicians spy on each other, he knows it all. And keeps on flaunting his knowledge and expert opinions.

He is the ultimate, undisputed world champion of bullshitting in the workplace and could be the motormouth in University seminars, forever talking in an attempt to score participation marks from the professor. People in his project teams may find it difficult to get a word into the discussion.

This guy might have no failures in life to date, cos he’s Mr Smart-Ass.

If the girl on the First Date probably shares a small issue in her personal life on the First Date, he would mutter That’s a small issue. Been through it a million times. Its simple to solve anyway. You should do this and that…”

Mr Smart-Ass can potentially advise the girl on anything by the end of the First Date. And he will probably hate Mr Universe. Their egos are too big to be in the same room.


3) Mr Indecisive 


This dude does not take the lead. He probably does not want to risk taking the girl to a restaurant that she might dislike, or simply just dosen’t like making decisions at all.

Furthermore, he tends to seek approval from the girl and asks her if its okay for him to bring her to whatever place, all the time. (Of course if she has some dietary restrictions, then its wise to ask beforehand)

A female colleague once complained to me:

“That guy I went out with last week kept asking me if we should watch this movie or the other, and what we should eat. I mean, if he wants to freaking take me to watch some show, just bring me there!”

“I manage a team of executives at work; does he want me to manage the date as well? Approve and sign off on every single activity he proposes?”

He shall be friend-zoned. Signed, sealed and delivered. He might genuinely be a nice guy, but his lack of confidence will limit his chances.


4) Mr Negativity


This guy tends to whine and complain and do the more of the same incessantly on a First Date – whether is it about his miserable love life, how treacherous or despicable his colleagues, or how biased his parents are towards his younger siblings.

He may have had a really rough patch recently, or probably just like to share his problems. Well… he might wanna save his woes for the male buddies over a drink but not on a First Date. Or share it when he has stronger emotional connections with the girl. But definitely he should not talk about his issues on the First Date.

A guy who keeps says negative things to a girl on the very First Date might end up putting her in a negative state instead. The girl won’t feel happy and excited about the whole date, and she might think she has found a new profession as a psychologist.

When the girl tries to encourage him about a certain bad situation, he responds with skepticism and mutters that things won’t get better.

Think about this for a second. Tomorrow, go run to a colleague or friend and exclaim ‘Hey I’ve got a GREAT piece of news to tell you!’ Chances are, he/she might be excited by your sentence and beg you to share more details.

You have put that person in a happy and excited state. Conversely, you can also easily put a nice girl in a negative mood on a date with the things you say.

What’s that with the phrases ‘Happiness begets happiness’ or ‘Laughter is contagious’? Well this logic probably holds true for negativity. It just doesn’t correlate with initial romantic attraction.

Mr Negative won’t attract many girls as people tend to love hanging out with positive and happy people.


5) Mr Pitiful


A close cousin of Mr Negativity, this dude tries to appeal to the softer side of women and attempts to gain sympathy or admiration for the hardships that he has been through. He probably got confused between love and sympathy.

Recently, a female friend lamented to me about this guy who has been pursuing her recently. “You know this guy SMSed me that day and told me that he was feeling very sick. (he was down with just a common flu actually) He took pictures of his numerous bottles of medication and sent them over to me via Whatsapp. I mean, why does he want to send me such photos? Isn’t he just so weak?”

Attraction is not built through sympathy.


6) Mr Super Tough Guy


This guy really really wants to prove his masculinity to the ladies. On the First Date, he talks a lot about his gym regime and his fitness levels to a girl who doesn’t exercise, and laments that he can ‘only’ do 12 chin-ups now compared to his peak which was 30 or something. Instead of checking out his hair when walking past glazed doors, he checks out the shapes of his biceps and deltoids.

For girls in Singapore where it remains as one of the few countries around the globe that has mandatory military service, did you ever go out on a First Date with some bald army boy in the past?

Did he ALWAYS talk and talk about how grueling and vigorous the training was? Or show you some of the cuts he got after getting tangled in barbed wire while negotiating an obstacle course? Were you attracted to his stories of bravado and then fell in love with him cos of that?

If the guy is really tough, he does not need to constantly prove it.


7) Mr Boring Interviewer


Yes of course, both parties are getting to know each other on the First Date and ask questions about each other. However, this guy does not draw the line at asking about boring and dreary topics all the time.

He asks questions about the girl’s family history dating back generations in great detail. Probably he is afraid that she might be his common cousin like Barney and Robin on How I Met Your Mother.

Or asking the poor girl about the numerous intricacies about why she selected her career path and worse still, asking her a lot about her previous relationships which might invoke some bad memories from her.

Perhaps he just ran out of things to say to the girl and desperately wants to plug the gap.

Boring a girl on the First Date will almost always not make her feel attracted to this guy.

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.Stay Cool, Be Willing to unlearn & learn!



5 thoughts on “7 Types of Guys Who Screw Up The 1st Date

  1. Pingback: Misleading Advice About Finding The Love Of Your Life | WEALTH. LOVE.

  2. Pingback: 6 Ways Dating Is Just Like Marketing A Product | WEALTH. LOVE.

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