The 100 approaches challenge: a 10-week plan
The 100 approaches challenge borrows its logic from rejection therapy. Jason Comely, an IT freelancer from Cambridge, Ontario, created that game around 2009: get rejected at least once a day for 30 days. Jia Jiang stretched it to 100 days and gave a TEDxMtHood talk about it in 2015, then wrote the book Rejection Proof. One thing he reported was that many nos turned out to be circumstantial, not personal.
The dating version swaps the unit. You start 100 conversations with people you're attracted to and count every one, yes or no. The goal is completing the count. Hit rate is secondary.
This page is the plan: what counts, how fast to go, what to write down, and where to check in.
What counts as an approach
Use one definition for all 100 and don't change it midway.
- You started the conversation with someone you were attracted to.
- You said more than "hi" or a door-holding nod. Aim for at least three or four exchanges.
- It ended with a clear answer: a number, a friendly goodbye, or a polite brush-off.
In Run Game, you log Success or Rejected, and both count toward your total. If you walked toward someone and veered off, or talked yourself out of it, jot it in your session notes and keep going. Hesitations stay out of your count.
So the challenge is 100 successes plus rejections combined.
The 10-week schedule
Two outings a week is enough. Each outing is 60 to 90 minutes.
| Weeks | Per outing | Per week | Running total |
|---|---|---|---|
| 1-2 | 3 | 6 | 12 |
| 3-4 | 4 | 8 | 28 |
| 5-10 | 6 | 12 | 100 |
Week 1 is deliberately small. If you can't hit 3 in an outing, the fix is to warm up, not to lower the target: spend ten minutes on warming up before you go out, then start.
Mix venues. By approach 50, have at least 15 in a setting that's new to you. If you only go out at night, do a daytime outing. If you only do daytime, try an evening. Day and night approaches have different rhythms, and trying both shows you which one you avoid.
What to log after each approach
Log within five minutes. In Run Game, log it as Success or Rejected. Then add one line in your notes app:
#37 | Sat | cafe | opener: "Is that book any good?" | 4 min | ended: number | change: said I liked talking to her sooner
Fields that matter: count, day, place, what you said to open, how long it lasted, how it ended, one thing to change. Skip names, descriptions and anything that could identify the person. This is a record of your behavior.
Group each outing into a Run Game session so you can compare nights.
Checkpoints
Review at 25, 50 and 75. Set aside twenty minutes each time.
At 25: Count the hesitations in your notes. If they outnumber your approaches in the last two outings, the next 25 are about starting, so use approach anxiety drills first. Todd Valentine, a former RSD instructor, describes a beginner's success as walking up to someone and saying something. Make that your bar for the slow nights.
At 50: Pull up your funnel. How many conversations produced a number, how many of those got a text back, how many became a date? Find the biggest drop. That's your sticking point for the second half. Also check your venue mix.
At 75: Look at what you open with. Which three openers did you use most, and which ones led to the longest conversations? Pick the two that feel most like you and use them for the last 25.
At 100: Compare approach 1 to 10 against 91 to 100 using your own notes: how long you hesitated, how long conversations ran, how you felt afterward.
Rules
- Respect the first no. "No worries, have a good one," then leave. A rejection counts the same as a success. Pushing past it adds nothing to your total, and a no or a walk-away means stop.
- Pick your moments. Headphones in, rushing, or deep in conversation with a friend means skip it. Note it in your session notes if you like, but it isn't an approach.
- Only approach people you want to talk to. Reps build skill when they're real attempts. An approach made only to bump the count teaches you little.
Common mistakes and fixes
| Mistake | Fix |
|---|---|
| Doing 10 in one night to catch up | Cap it at 8 per outing. Rushed reps teach less than 3 real ones. |
| Stopping when one goes well | Finish the count. Decide deliberately, at a checkpoint, if you want to stop. |
| Only approaching when it looks easy | Every fifth approach, pick someone you'd normally skip. |
| Comparing your pace to someone online | Use your own table above. Your pace is the one you can sustain. |
| Logging from memory on Sunday | Log within five minutes. Memory edits out the awkward moments. |
| Dreading every outing | Take a week off, then resume at the previous week's target. |
| Skipping the bad nights in your notes | Write them first. They hold the most information. |
What to do next
- Today: Write your definition of an approach in your notes app and set a start date.
- This week: Schedule two 60 to 90 minute outings and put them in your calendar. Target 3 approaches each.
- Before each outing: Do ten minutes of low-stakes warm-up, such as asking for directions or a recommendation. If you want a harder on-ramp, try rejection therapy for a few days first.
- After each approach: Log Success or Rejected in Run Game, then write the one-line note.
- Sunday: Spend ten minutes on the weekly numbers: approaches, hesitations from your notes, venues, and your one change for next week. A short field report after your best and worst outing each week is enough.
- With a friend: If someone else is doing it, compare weekly totals on the Friends tab's weekly board. Going out alone vs with a wingman covers how to split the work.