The Day I Became a Pickup Artist (End of Date Coaching)

This is part 5(c) and the last part of my review series with Lunch Actually, a lunch dating company in Asia, after trying out their service in 2012. If you haven’t, check out part 1: Joining Lunch Actually, part 2: Initial Consultation and Membership Enrollment, part 3: Going Through Image Coaching!, part 4: The Date Process!, part 5(a): New Date Coaching Series, Part 1!, and part 5(b): Wheel of Dating before reading this post.

Last Tuesday, I took a break from my usual duties as a life coach and donned a role which I never in my life thought I would take on — a pickup artist.


That’s right, I became a pickup artist. Well, for that one day anyway. ;)

Celes, The Pickup Artist—My Challenge

This was a challenge that my date coach (Kydon) set for me—to approach and converse with random strangers (guys) in a shopping mall. While I’m not unfamiliar with being picked up / hit on by guys, I had never (up until that point) tried to hit on guys before. The challenge started off with me asking for simple directions, after which it got harder and harder, ultimately culminating into me asking for their number, and finally… *drum roll* to ask them to be my boyfriend! (Yes, I’m serious!)

While this was somewhat crazy, I gamely took up the challenge. I’m never one to back down from a challenge, especially not one as outrageously ridiculous as this one. ^_^* I love it when I get to do ridiculous stuff like this, because it makes for great experiences, learning lessons, and funny hi-jinks. I have always thought that it would be fun to put aside my usual self, behave completely out of character for a day, “mess” around with the regular person on the street, and sit back and enjoy their responses. Think The Sims or even Sleeping Dogs. This was my perfect opportunity to do so.

The challenge took place at Plaza Singapura Shopping Mall, next to Dhoby Ghaut MRT Station. I was there with 3 other ladies — Kydon’s clients who were asked to do the challenge as well. The pickup challenge lasted 2 hours. Some pickups were paired efforts while some were individual conquests.

My verdict? My ego was completely crushed at the end of the stint. ^_^* Every stage went swimmingly well, even including the part where I asked for the guys’ numbers… up until I asked them to be my boyfriend (LOL). This was where I received violent (negative) reactions where the guys reacted extremely rudely!! By the end of the night, I had become a woman of no fear.

My Assigned Pickup Lines and Objectives

Here are the different legs of the challenge, in the order Kydon had assigned me. Each phase was executed on a different, unsuspecting male passerby in the mall.

  1. “Excuse me… can you tell me what is the way to Park Mall?”
    • Objective: To get the guy to help you with directions
    • Difficulty: Easy, since this is something I do regularly to begin with (I’m bad with directions)
  2. “I’m going to a friend’s house party this weekend. What would you recommend me to get for my friend?”
    • Objective: To get the guy to open up and help you with the faux house party you are going
    • Difficulty: Normal. As house parties are not exactly a norm in Singapore, you have to be very welcoming and open in your approach to have the person to help. Otherwise, most would just say “I’m not sure, sorry about that”.
  3. “My friends and I are having a tossup between watching Resident Evil and Ted. Which movie would you recommend us to watch?”
    • Objective: Get the guy to open up by talking about the movies
    • Difficulty: Surprisingly easy. Seems like maybe movies is a very relatable topic, and one which people can be emotionally invested in, and hence people were readily able to offer opinions.
  4. “I’m trying to convince my friend to join Facebook. What would you say are the pros and cons of Facebook?”
    • Objective: Get the guy to voluntarily share about Facebook. Then, try to get his Facebook account details or get him to add you on Facebook
    • Difficulty: Hard! It was weird bringing up the topic of Facebook which was not related to the context (we were in a shopping mall), so the key was to find a good angle to weave into this topic. I found that when I didn’t succeed in doing so, the guys felt that something was amiss and immediately backed off, while when the transition was done well, the guys were very ready to share.
  5. “I’m looking for a dessert place. Do you know what is the best dessert place around here?”
    • Objective: Connect with the guy through the topic of desserts
    • Difficulty: Easy
  6. Combine 2-3 of the conversation starters above.
    • Objective: To learn to converse across different topics
    • Difficulty: Easy
  7. Use whichever conversation starter you desire. Then, ask to take a picture with the guy at the end of the conversation.
    • Objective: To get the guy to warm up enough to want to take a picture with you
    • Difficulty: Slightly difficult. I was concerned the person might think I was some stalker person (as if the other legs of the challenge didn’t already project me as a stalker to other guys). But I did successfully get a picture with 2 guys in the end (see below).
  8. Use whatever conversation starter(s) you desire. Then, ask for the guy’s number.
    • Objective: To get a guy to give his number to you voluntarily through *cough* feminine wiles and good conversing techniques
    • Difficulty: Surprisingly easy (for me) actually. I got 2 numbers out of the 2 guys I approached—and both were pretty good-looking gentlemen too! One even smiled gently when I asked for his number, as if he realized that that was why I had approached him to begin with!
  9. “Hi, you look really handsome. I’m looking for a boyfriend. Will you be my boyfriend?” (LOL. *facepalms*)
    • Objective: To push your courage by asking an outrageous question to a random stranger (obviously no sane person would say yes to this question!).
    • Difficulty: Unspeakable. I could feel a block in my heart as I attempt to execute the task—after which I just ignored it and did it anyway. I’ve to say that the violent responses of shock and rejection from the guys really didn’t help remove the block too!
Celes the Pickup Artist

Two of the guys I chatted up on the day. Got a picture with them!


Celes the Pickup Artist, #2

Chatting up some clueless stranger. I believe we were asking him about movies in this picture.

Celes the Pickup Artist, #3

Here we were discussing with him about Facebook and its pros and cons. Poor lad must have been wondering what exactly we were up to, stopping him in the middle of his shopping experience and asking him about Facebook!

5 Lessons from My Day as a Pickup Artist

While this whole pickup stint may seem like some frivolous activity done out for thrill and humor, Kydon’s intention was to get us to open ourselves up to do things outside of our comfort zone. After unabashedly approaching like 15 men that evening, I picked up the following lessons for myself:

  1. The way you start a topic can have a great impact in how the person responds.
    • For example, for the topic on desserts, I used an angle of: “Hi, my friend just broke up with her boyfriend. :/ I’m looking for a good dessert place for her. Would you be able to give any recommendations?” Because of the emotional nature of the situation, I felt the guys were more sympathetic and helpful than if I had just asked, “Hi, do you know of any good dessert places?”
    • Of course, I had only done the above as it was in the context of the assigned challenge; in real life I wouldn’t cook up some fake story just to connect with others. Also, sympathy isn’t necessarily the emotion you want to elicit in a conversation — my point here is how you open your topic affects the response you will get. Learn to connect with others through meaningful stories and heartfelt intentions, and others will reciprocate in kind. Don’t cook up stories and use false emotions to get people to connect with you — authenticity is the most important thing at the end of the day.
  2. People’s reactions give you insight into the kind of people they are.
    • Despite using the same line to different guys, I received different responses. Some were helpful, some weren’t; some were brash, some were gentle and kind.
    • For example, the 2 guys who willingly gave me their numbers, with a gentle smile to boot, were very good-lookers, while the 2 guys who (quite violently, might I add) snubbed my boyfriend request were in very bad physical shape and not groomed at all. One rolled his eyes and shouted very loudly, “SORRY NO, I’M GAY” (it’s obvious he wasn’t and was being rude), while the other rolled his eyes at me and said very harshly, “NO!“While I don’t normally judge people based on appearances, in this case (based on the data points I have) it was apparent that the latter group was reacting from personal insecurities and hangups, especially since my question could be considered a compliment. On the other hand, the former group, probably being more assured in themselves and looks, didn’t react with any trace of negativity or insecurity at all; if anything they were very friendly.
    • Perhaps you may think, You were asking the person to be a boyfriend, how else can someone react but violently? Now the thing is the emotions of surprise and anger/disgust can be separate. Someone can be surprised and reject another without any tinge of anger/disgust. For example, I’ve been approached many times before, including with a direct request asking me to be the person’s girlfriend (and I’m talking pickup encounters here), and I have never reacted with anger/disgust before. Surprise, shyness, embarrassment, flattered yes, but not no anger/disgust at all. I mean, what’s there to be angry/disgusted about? I would then merely smile, say “No, thank you”, let the person know that it was a very kind request and that I hope he would find a more suitable girl for him in the future.
    • My thought: We often fault ourselves with what people say because we feel it has to do with ourselves. What if it doesn’t have anything to do with you, and has to do with the other party instead? Something to chew on.
  3. People are fundamentally helpful.
    • I was pretty amazed that some people actually took the time to meticulously answer my pick-up questions, especially #3 (which movie to watch) and #5 (best dessert place). I thought most would just brush them away as some lame pick-up attempt and walk away. It shows that people have good hearts and you just have to find the key to their hearts.
  4. Fear is nothing but a state of mind. It does not exist in reality.
    • Most stages in the challenge were actually very doable for me. Where I faced some resistance were the parts where I had to get a picture, ask for the guy’s number, and ask the guy to be my boyfriend. I could only surmise these blocks as feelings of fear.
    • Yet, I knew these feelings of fear was only mental, not real. All my personal development have taught me that fear is but a figment of your imagination. When faced with fear, you can either be at its mercy and let it hang over you like a shadow, or feel it and walk through it anyway.
    • So I did that — felt the fear, and walked right into it anyway. In the end, I am still alive, the world is still spinning, and people are still walking around me, going about their daily activities. The only thing that has changed is that my perception of reality has now expanded — what I thought was “dangerous” before (asking “bizarre” questions like asking people to be my boyfriend) had clearly proven itself not to be dangerous!
    • (By the way, watch the eighth commercial (Dare) in 20 Amazing Commercials to Inspire the Greatness in You. It’s a great commercial on the different fears we face in life, feeling them, and walking through them anyway.)
  5. Your fear is a reflection of your personal hangups.
    • I did the pickup artist challenge with 3 other ladies. It was interesting to see that they had difficulties with certain legs of the challenge where I didn’t (some of them didn’t get to the boyfriend stage as it was too much for them, though understandably so). It reinforced lesson #4 in that fear is nothing but a state of mind. In fact, I would say that our fears are likely reflections of our personal hangups.
    • For example, I didn’t have issues with the conversational aspects of the challenge since connecting with people and communication is something I do on a daily basis; they are my passion. On the other hand, I felt blocked when I had to ask a random stranger to be my boyfriend. It was likely because it felt brash, unfeminine, and unorthodox — all of which were things which I’m not interested to be.
    • Breaking these personal barriers have helped me realize that it is okay to cross the boundaries ever so often, in a conscious manner. It is not about always sticking to one side of the fence, but knowing what both sides represent to you and walking along the side that’s required at the point in time (while sticking to your core values).
    • Related post: 5 Myths Keeping You from Finding Love

On top of the 5 lessons above, it goes without saying that your body language is important to elicit the most welcoming responses. Things which I’ve to work on including keeping an open body language (I’ve a habit of holding my hand close to my heart while speaking, which might create an impression that I’m fearful when I’m actually not) and having a more welcoming posture when conversing. (Kydon said my standing posture is very straight, which makes me appear very serious. The funny thing is that having this posture is probably useful when it comes to professional work!)

A Day as a Pickup Artist: Aftermath

The next day, I couldn’t look at male strangers the same way anymore. I kept thinking about how I should approach each guy I saw and strategize how to ask him to be my boyfriend! (LOL.) I didn’t, of course. It was merely a funny thought that cycled through my mind.

It took me a day to get that out of my system.

Update: Ending My Date Coaching Sessions

Update, Oct 2012: So after one month of intensive dating, various date coaching sessions, and various intense situations that made me reflect a lot about what I want in my life and love, I feel that I have developed my own voice where it comes to dating and romance. As such, I have decided to end my date coaching sessions with Kydon, and create my own path and make my own decisions in the area of love and romance.

Part of the reason is because I feel that continuing the sessions would make me lose sight of my own agendas and goals, because being part of the sessions meant that there would be certain agenda/timeline to meet revolving dating (since the very nature of the coaching is date coaching) and it wasn’t in line with my personal ethos in that I feel love should happen organically, not by a timeline.


Having fully immersed myself in dating in September though, today I know where dating and romance stands in my life. I know that dating and love is something that I want; at the same time, I do not wish for it to consume my life. Where dating is concerned, I would like for it to happen as I live my life, and not something I put my life on hold to do.

The reason I dove headfirst into dating at first was because I always like to go full throttle in something to experience it fully and see what comes out of it, before making any conclusions. This immersion has been instrumental in my growth in love and relationships. The tips I share in 10 Steps to Attract Authentic Love ring even truer after this episode.

Moving forward, my focus is to work on my next long-term direction for PE, design the upcoming webinar (likely on overcoming procrastination or increasing productivity), and create more great content. Stay tuned guys! :)

Update 2013: 7 months after writing this series, I met my soulmate. :) You can read about my love story and my guide to find your soulmate here: How To Find Your Soulmate (series)

This is part 5(c) and the last part of my review series with Lunch Actually, a lunch dating company in Asia, after trying out their service in 2012.

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