M2M Skill #1 — Social Skills/Dating: The Challenges

The Challenges

The way I’ve structured these challenges, is to have each challenge build off the next. As a result, the next day will combine the previous days challenge.

Each challenge will focus on a specific aspect of social skills. Keep in mind, the principles apply to all social interactions.


  • Each learning session (challenge + reflection + research) must be completed in under 2 hours (except the challenge #28,#29,#30). Otherwise, this counts as “fail.” Only exception, is if I get into a good conversation. This will need to be a judgment call. This will force me to take action and not linger around. I also have other things to do in my life.
  • Environment does not matter. It just needs to be an environment where there is high volume of people + I can remain anonymous (clubs, tourist areas etc.)
  • When approaching everyone, do not discriminate towards certain races, age groups, stereotypes. Only exception is homeless people or those green/red vest people trying to get me to sign their petition.
  • Don’t talk about fight club aka do not tell people about this project when I talk to them.
  • When approaching women, due to time constraint, lower the attractiveness bar for approach to maximize social interaction.
  • I can only change the challenges but to a challenge that is more difficult than what’s currently there.

The Challenges:

Day 1: 3-Second Rule: Approach 10 people on the street. After spotting someone, approach within 3 seconds. If across the street, run across the street.

Day 2: High five 25 strangers.

Day 3: Having Fun: Memorize a funny joke, approach 10 people and tell them a joke. Try to get them to tell you a joke back.

Day 4: Bring speakers or wear headphones. Go to the middle of a crowded area. Dance for at least 3 minutes. Record on video.

Day 5: Asking for what you want: Walk into 5 different stores and try to get something for free. Spend at least 1 minute trying to persuade them.

Day 6: Persistence: Try to convince 10 people to buy something random. Persist for 60 seconds.

Day 7: Smiling: Approach 20 people. Start a conversation and focus on walking up with a smile.

Day 8: Question-Answer-Statement: Approach 10 women. Ask a question and respond with a statement.

Day 9: Body Language: Approach 10 people. Start a conversation. Get to neutral body language as soon as possible.

Day 10: Banter: Approach 10 women and try to get into a fun banter with her. Memorize a few lines as backup.

Day 11: Sick — Did six approaches

Day 12: Emotional Statement: Approach 10 people and throw in an open-ended question and respond with a shared emotional statement.

Day 13: We statement: Approach 10 people and use a “we” statement or use “us” mentality.

Day 14: Qualification: Approach 10 people, start a conversation and try to get them to qualify themselves to you. Bonus points for disqualifying self.

Day 15: Looks: Approach 10 people with food on my face.

Day 16: Opening Line: Approach 10 people and open them using vulgar rap lyrics.

Day 17: Environment: Approach 10 people in an environment I don’t usually approach in. Bookstore, restaurant, public transportation.

Day 18: Environment: Approach 5 people sitting down. Sit with them, start a conversation and use a time constraint.

Day 19: Groups: Approaching 10 people but they must be in a group.

Day 20: Casual: Approach 10 people, without deliberately going out. Approach as you’re going about your day.

Day 21: Stereotyping: Approach 10 people I don’t usually approach

Day 22: Take-away: Approach 10 people and try to use a take-away (she must be interested for it to work though).

Day 23: Shit tests: Approach as many people as I can until I get a shit test.

Day 24: Man-Woman: Approach 10 women and use a “Man to Woman” statement.

Day 25: Excuses: Approach 5 people that are on the phone.

Day 26: Persistence: Approach 10 people. Try to stay in conversation for at least 5 minutes each.

Day 27: Persistence: Try to get 10 phone numbers. Get rejected. Persist and try a different angle.

Day 28: Instant Date: Approach until you get an instant date.

Day 29: Approaching: Walk into a bar and introduce yourself to EVERYONE in the bar.

Day 30: The Final: Have 100 stranger interactions using everything learned in a day (male or female)

After this challenge, I’ll likely aim for more of an indirect strategy with social groups towards meeting women. However, I should have the channel open, for whenever I see an attractive girl in any environment. I’ll keep approaching while going through my other challenges to maintain the skillset, just reducing the quantity & intensity of practice.

Next Month — 40 Consecutive Pull-Ups