Imagine you're texting a girl.

Me - So when are you free?

Her - I might be free this weekend

Me - Okay. How's Saturday at 8 work?

No response.

I've fallen for this trap plenty. It's the worse. Do you see what went wrong there?

"Maybe."

"This weekend."

Two very vague times. The weekend is Friday to Saturday, and maybe is just...well, it's a maybe.

If you respond to purposeful ambiguity with hard action, you might find yourself slipping into a trap. She was showing half interest and you went 0 to 100. Instead, you should move as cautiously as she's playing. You COULD make the right move by barreling forward, but it's risky.

Try this next time

You - So when are you free?

Her - Maybe this weekend?

You - Haha that's so vague

See what you did there? You're teasing her without being butthurt. It might continue like this

Her - lol im sorry. I'm terrible at making plans

Me - I can see lol

Her - Hm...okay I think Saturday is good

I've seen it happen. She was on the fence about you, threw out a half acceptance, but you played it well by moving at her speed and taking sidesteps. She respected your skill and opened up her schedule freely.

It might not always go so smoothly.

You - So when are you free?

Her - Maybe this weekend?

You - Haha that's so vague

Her - I just don't know when I'll be free

You - Okay. Well let me know when it clears up

Her - Ok

You might hear from her, you might not, but she didn't give you anything to work with. However, you stand a much better chance of getting a date than if you tried to wrestle your way to a date.

What signs should you look for to play it like this?

Anytime she

  • Uses "Maybe" or "Might"
  • Puts a question mark on her schedule, e.g., "Idk Friday?"
  • Is outright ignorant (e.g., "i'm not sure")

If you see this, pause, and tread slowly.

Hector Castillo