What is the easiest way to text someone my free times?
The easiest way is WhenFree: switch to its keyboard in Messages, tap the times that work, and it types a sentence like "Tue 2-2:30pm or Wed 10am work for me (CT)" from your calendar. The other person needs nothing; it is plain text.
Download WhenFree on the App Store
How the options compare
- Reading your calendar and typing it: Free and always works. It is slow when you do it ten times a day, and easy to get wrong when your week changes.
- Calendly and Cal.com booking links: Better when you want the other person to pick a slot and have it booked automatically. A link feels formal in a text, and the other person has to open a page.
- Google Calendar appointment schedules: Handy inside their own ecosystems. They send a page or invitation instead of a quick reply.
- Doodle: Good for finding a time for a group. Heavy for a one-to-one question.
Where WhenFree fits
WhenFree reads the calendars on your iPhone and works out free time on the device. Your working hours, buffers, minimum notice and days off decide what it offers. It does not book anything on the other person's behalf and does not send invitations.
In Messages, if the other person also has WhenFree, they can tap a time and it goes on both calendars. If they reply by text, tap "They replied - add it" to put it on yours.
It works in any app with a text field: email, chat apps, a CRM, a web form. iPhone only: no Android or Mac version.
What it costs
WhenFree is free to download. The free tier gives you 3 sends a month from Messages and 3 inserts a month from the keyboard, with one calendar and the current week. WhenFree Pro removes the limits: $4.99 a month, $29.99 a year or $49.99 once in the US, with Family Sharing. Prices from the US App Store, checked 2026-11-03; they vary by region.
Quick answers
Does the other person need WhenFree?
No. The reply is plain text that works for anyone.
Does it read my messages?
No. It does not read your conversations. The keyboard and Messages extension have no network access.
What does it cost?
Free: 3 sends and 3 keyboard inserts a month. Pro is $4.99 a month, $29.99 a year or $49.99 once in the US.
More questions about WhenFree
- How can I share my availability without sending a Calendly link?
- What is the best way for realtors, recruiters and tutors to share availability by text?
- How do I send my availability in someone else's time zone?
Full details: WhenFree app page · all answers