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

This is part 5c and the last part of my review series on Lunch Actually, a lunch dating company in Asia, after trying out their service in 2012. Opinions expressed here are my own.

(Published on Oct 3, 2012)

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

Being Pickup Artist—My Challenge

This was a challenge that my date coach, Kydon set for me — to approach and converse with random guys in a shopping mall. While I’m not unfamiliar with pick-up attempts, I had never tried to hit on guys before. The challenge started with me asking for simple directions, after which it got harder and harder, ultimately culminating into me asking for their number, and finally, to ask them to be my boyfriend. (Yes, I’m dead serious.)

While this was absolutely crazy, I focused on the plus side and thought it would be interesting to put aside my usual self, behave completely out of character for a day, and see what unfolds.

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

My ego was completely crushed at the end of the stint. Every stage went really well, including the part where I asked for the guys’ numbers… up until I asked them to be my boyfriend. This was where I received a mix of positive and violent (negative) reactions! 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 my date coach 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 XXX?”
    • Objective: To get the guy to help you with directions
    • Difficulty: Easy
  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 thinking between watching X movie and Y movie. Which movie would you recommend us to watch?”
    • Objective: Get the guy to open up by talking about the movies
    • Difficulty: Very easy. Seems like maybe movies is a very relatable topic, and one which people can be 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 a stalker  (as if the other legs of the challenge didn’t already project me as a stalker). But I did successfully get a picture with two 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 good conversing techniques
    • Difficulty: Surprisingly easy (for me) actually. I got two numbers out of the two guys I approached, who were both great looking as well. One even smiled 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?” (*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 have 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

Talking to some clueless stranger. I believe we were asking him about movies here.

Celes the Pickup Artist, #3

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

5 Lessons from My Day as a Pickup Artist

Kydon’s intention of this challenge was to get us to open ourselves up to do things outside of our comfort zone. After approaching about 15 men that evening, I picked up the following lessons for myself:

  1. How we start a topic can impact how a person responds.
    • I noticed that when I opened the question with some personal sharing (e.g. for the topic on desserts, I said that my friend had just broken up and I was looking for a good dessert place for her), the guys were sympathetic and helpful. This was probably so more than if I had just asked, “Hi, do you know of any good dessert places?”
    • Of course, I was only doing this whole thing in the context of the assigned challenge, which, thinking back, I wouldn’t do again if I had a choice (more on this at the end of the post). Don’t cook up some fake story just to connect with others. Learn to connect with people through heartfelt intentions, and others will reciprocate in kind. Honesty is the most important thing at the end of the day.
  2. People’s reactions speak about themselves too.
    • Despite saying the same thing to different guys, I received different responses. Some were helpful, some weren’t; some were brash, some were kind.
    • For the shocking question of “Would you be my boyfriend?”, I had two wildly different responses — positive responses from two guys who happened to be good lookers and gave me their numbers with a smile; and violent, aggressive, and angry responses from two other guys who appeared unkempt and did not pay much attention to their own grooming and physical outlook (these two guys were unrelated and were individually approached, both rolled their eyes and shouted loudly at me). It did feel that the latter group was reacting from certain hang ups or personal negativities, especially as my question could be considered a positive remark. The former group didn’t react with any trace of negativity; if anything they smiled and were very friendly.
    • While you may think, You were asking the person to be a boyfriend, how else can someone react but violently?, emotions of surprise and anger/disgust can be separate. Someone can be surprised and reject another without any tinge of anger/disgust. I’ve been approached before, including being asked to be a stranger’s girlfriend (two different encounters), and I have never reacted with anger/disgust before. Surprise, embarrassment, yes, but not anger/disgust. For each incident, I merely smiled, thanked them, and wished them luck in finding a more suitable girl for them 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 think about.
  3. People are fundamentally helpful.
    • I was amazed that some people took the time to meticulously answer my questions, especially Q3 and Q5. I thought most would just brush them away and walk away. It shows that people have good hearts and really wish to lend a helping hand to others.
  4. Fear is a state of mind. It does not exist in reality.
    • Most stages in the challenge were 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 the fear was mental, not real. My experiences with personal growth have taught me that fear is a figment of our 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, life still went on. What has changed is that my perception of reality has now expanded — what I thought was “dangerous” before wasn’t physically dangerous, just something “dangerous” in my mind.
  5. Our fear is usually reflection of our personal hang-ups.
    • I did the challenge with three 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 to me that fear is a state of mind, and that our fears are likely reflections of our personal hang-ups.
    • For example, I didn’t have issues with the conversational aspects of the challenge as connecting with people and communication are things I do daily; they are my passion. However, I felt blocked on the boyfriend question. Besides it being ingenuine, it was likely because it felt brash, unfeminine, and unorthodox — things I’m not interested to be.
    • Related post: ‘Online Dating and Arranged Dating are Only for Desperate People.’ 5 Myths Keeping You from Finding Love

On top of the five lessons above, it goes without saying that your body language is important to elicit the most welcoming responses. I’ve written an article before on body language: Are You Keeping People Away With Your Body Language? (And 10 Tips To Improve Your Body Language)

My Afterthought (2013)

While I gamely did the above, it was largely because I was going through the date coaching and felt that I needed to follow through with the curriculum and what was asked of me, in order to experience the date coaching in its entirety.

It’s been a year, and thinking back, I wouldn’t have done this if given a choice again — because I did feel that it was disingenuous to approach people this way, asking false questions as a personal test — much less with very personal questions (e.g. the boyfriend question). These people were also not willing participants and were not in onto the challenge, so this kind of felt like it was against my personal values and ethos.

I also did not feel that the challenge really mirrored the kind of insights and growth needed in a true dating situation. The challenge constituted approaching random strangers and talking to them with a range of basic and deeply personal questions, to elicit a certain response, while a true dating situation is about understanding people, connecting with them as humans, and developing a two-way bond with each other.

The challenge definitely has its own personal growth lessons though, and I believe that it must have been helpful for the others who went through it (I had my own takeaways as I shared above). It also clearly achieved the objective of challenging ourselves and forcing us to confront our fears. So just my post-challenge notes. :)

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 path and make my own decisions in the area of love and romance.

Part of the reason is that 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 isn’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, 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 on 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 my next 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 5c and the last part of my review series on Lunch Actually, a lunch dating company in Asia, after trying out their service in 2012. Opinions expressed here are my own.