When someone says ‘whenever works,’ it can feel like a blank check — helpful, but also a little stressful if you don’t know where to start. Simple, steady wording reduces the pressure for both people and gets you a confirmed plan without sounding pushy. Use short choices or offer to pick a time so the conversation moves from vague to actionable.

Why This Moment Matters

Scheduling is how plans actually happen — vague answers delay decisions and can create friction, especially when calendars are busy. ‘Whenever works’ can be genuine flexibility or a gentle way to avoid choosing; reading the context helps you decide whether to take the lead. How you respond shapes whether the meeting gets booked easily or turns into repeated back-and-forth.

Short, Simple Things You Can Say

• ‘Great — are mornings or afternoons better for you?’
• ‘I can do Tuesday at 3pm or Wednesday at 10am — which do you prefer?’
• ‘Would you rather I pick a time and send an invite?’
• ‘Does later this week work, or should we aim for next week?’
• ‘I’m free Monday–Wednesday mornings — does any of those work?’

Longer Messages With More Warmth

• ‘Thanks — I appreciate the flexibility. I’m free Tuesday afternoon or Thursday morning; if one of those fits, I’ll send a calendar invite.’
• ‘Perfect — to make this easy, would you prefer a short catch-up (20 min) or a longer chat (45 min)? I can pick times that match.’
• ‘Totally flexible — if it helps, I can pick a time and change it if needed. How does Wednesday at 11am sound to start?’
• ‘I know schedules are busy, so I can offer two options: Thursday at 9am or Friday at 2pm. Let me know which works and I’ll lock it in.’

What to Avoid Saying

• Don’t respond with vague open-ended questions like ‘When works?’ that keep the conversation circular.
• Avoid sounding passive-aggressive: skip lines like ‘Whenever? That’s helpful…’ which can escalate tension.
• Don’t assume perpetual flexibility — avoid saying you’ll always pick without checking preferences first.
• Avoid overloading with too many choices (more than three) which can make the other person defer again.

Helpful Tips for Handling the Moment

• Offer 2 clear options (different days or morning vs afternoon) — two choices make deciding easier.
• Use a deadline: ‘If I don’t hear back by Wednesday, I’ll go ahead and book Thursday at 10am.’
• Mention time zones when relevant: ‘I’m in EST — does that still work for you?’
• Use scheduling tools (Google Calendar with suggested times, Calendly) if you coordinate often with busy people.
• If you truly prefer them to pick, say so: ‘If you know a time, tell me and I’ll make it work.’

A Note About This Particular Situation

How you respond should fit your relationship and the meeting’s importance — with colleagues be direct and use options; with close friends you can be more casual. Remember “whenever works” can be a courtesy rather than indifference, so offering a small set of choices honors their flexibility while moving things forward.

Let us know in the comments if this has helped or if you’ve got suggestions we can include

About the Author

Helen Bach is a relationship expert and writer who helps people find the right words when it matters most. She studied English and English Literature at the University of Michigan, where she developed a passion for how language shapes love, conflict, and connection.

At whattosaywhen.net, Helen writes clear, down-to-earth advice on what to say in real-life situations—from first dates and tough conversations to breakups and makeups. Her goal is simple: to make talking about feelings less awkward and a lot more honest.