Flow

The 100 approaches challenge

5 min read

The 100 approaches challenge is simple. You start conversations with 100 people you're genuinely attracted to, and you count every one, whatever happens. A yes counts. A no counts. The only thing that doesn't count is the one you talked yourself out of.

The point isn't to get 100 numbers or 100 dates. It's to make approaching ordinary. The first few will feel like a big deal. Somewhere along the way, they stop feeling like that, and you start paying attention to the actual conversation instead of your own heartbeat.

What you're counting

Be clear about this before you start, because it changes how the challenge feels.

You're counting your own actions. Not people, and not outcomes. "100 approaches" means 100 times you walked up and said something, not 100 women or men you've collected. That distinction keeps the challenge honest. It's a record of your nerve, not a tally of anyone else.

A reasonable definition of an approach:

Almost-approaches don't count. Walking toward someone and veering off at the last second is useful to notice, but it isn't a rep.

Set it up

Pick a timeframe

Give yourself a window long enough to be realistic and short enough to keep pressure on. A few months works for a lot of people. If you go out two or three times a week and do a few approaches each time, you'll get there without burning out. If that's too much, stretch it. A slower finish beats quitting at 30.

Decide how you'll track

A notes app, a paper tally, or a tracking app. What matters is that you log right after, not from memory at the end of the week. Memory is biased toward the awkward ones. There's more on why in why tracking your approaches makes you better at them.

Decide where you'll go

Mix it up. Daytime approaches in parks, bookstores, and coffee shops feel different from nighttime approaches in bars. If you've only ever tried one, the challenge is a good excuse to try the other.

What it tends to feel like

There's no reliable data on how a challenge like this goes, so treat this as a rough sketch, not a promise.

The first ten are usually the hardest. You'll spend more time hesitating than talking. Some nights, getting one done will feel like a win, and it is.

The middle stretch is where things start to get interesting. The fear is still there, but quieter. You'll start noticing what you do: maybe you always lead with a question, or you leave too early, or you talk too fast. These patterns are the useful part.

The last stretch is usually about refining. You'll be reading people better, you'll know which openers feel natural to you, and you'll have a much better sense of when to stay and when to say goodbye.

Everyone's pace is different, and progress isn't a straight line. You might have a run of easy nights and then a week where approach number 41 feels as hard as approach number 4. That doesn't erase the 40 before it.

Rules that keep it decent

A challenge with a number attached can push you in bad directions if you're not careful. A few rules:

Only approach people you'd actually like to talk to. Don't approach someone just to bump your count. That's treating people as practice equipment, and it shows.

Respect a no immediately. "No worries, have a good one," and leave. A rejection counts toward your total. Pushing past it doesn't make it count more. See handling rejection.

Read the situation first. Someone with headphones in, running for a train, or deep in conversation with a friend isn't a good approach. Picking your moments is part of the skill.

Don't speed-run it. Doing ten rushed approaches in an hour to hit a number is worse practice than three real ones. The goal is good reps, not fast ones.

Be honest with yourself. Don't count almost-approaches. Don't skip logging the ones that went badly. A challenge only works if the record is true.

Common pitfalls

Stopping after a good result. If approach 23 turns into a great date, it's tempting to call it done. Finish the challenge anyway, or at least decide deliberately to stop. The point was the skill, and the skill isn't finished.

Comparing yourself to others. Someone online did it in two weeks. Someone else got 40 numbers. Neither of those matters. You're building your own comfort, at your own pace.

Burnout. If you're dreading every outing, slow down. Take a week off. A challenge you finish slowly is worth more than one you abandon.

Only doing the easy ones. If you only approach when conditions are perfect, you'll finish the count without stretching yourself. Push a little past comfortable now and then.

Make it easier

Warm up before each outing. A few small interactions before the first real approach make a big difference. Warming up before you go out has a simple routine.

Practice hearing no first. If you're stuck before you even start, rejection therapy is a good on-ramp.

Bring someone. A friend doing the challenge with you makes it easier to stay consistent. Going out alone vs with a wingman covers the trade-offs.

Review every week. Look at what's working and what isn't. A short written note after each outing helps. If you want structure for it, there's a format in how to write a field report.

When you finish

At 100, you'll have a pile of evidence that approaching is survivable. You'll have stories, some good and some cringe-worthy. You'll probably understand your own habits a lot better. And you'll likely find that approaching someone you're interested in feels much less like jumping off a cliff and more like starting any other conversation.

What happens next is up to you. Some people start another 100. Some shift their focus to dating someone they met. Both are good outcomes.

Flow fits this kind of challenge well. You log each approach as Success, Rejected, or Pass from the home screen, and only successes and rejections count toward your total, which matches the rules above. Streaks track consecutive days you log, Sessions group a night out, and the weekly friends scoreboard is a low-key way to stay consistent if a friend is doing the challenge too.