People often say ‘I guess’ when they’re unsure, uncomfortable, or trying not to make a big deal of their true feeling. When someone tells you ‘I guess,’ a calm, curious response can help them clarify what they mean without feeling pushed or judged. The goal is to invite clarity and show you care about their perspective.

Why This Moment Matters

‘I guess’ can be a signpost: it may mean hesitation, politeness, doubt, or an attempt to soften disagreement. How you respond shapes whether the person closes down or opens up. A thoughtful reply can turn an offhand, uncertain comment into a clearer, more honest conversation — or, at minimum, prevent misunderstandings.

Short, Simple Things You Can Say

• ‘What do you mean by that?’
• ‘Can you say that again?’
• ‘Do you feel unsure about it?’
• ‘Help me understand where you’re at.’
• ‘That sounded hesitant — do you want to talk more?’
• ‘Is there a part you’re not sure about?’

Longer Messages With More Warmth

• ‘I hear some hesitation. It’s okay to be unsure — tell me what’s making you say ‘I guess’ so we can figure it out together.’
• ‘Your opinion matters to me, even if you’re not certain. Would you prefer to wait and decide later or talk through what makes you unsure?’
• ‘Sometimes ‘I guess’ is a way of protecting yourself. If you’re comfortable, I won’t rush you — just tell me what you’re leaning toward, and we can take it from there.’
• ‘I appreciate you sharing that, even tentatively. If you’d rather, we can break it down step by step so it’s less overwhelming.’

What to Avoid Saying

• ‘Don’t be wishy-washy’ — dismisses their feeling and shuts the conversation down.
• ‘Well, I guess…’ — answering hesitance with your own uncertainty can be confusing.
• Pressuring them with ‘Decide now’ or ‘Just pick one’ — forces a quick answer they may regret.
• Ignoring the hesitation and moving on as if it didn’t happen — misses an opportunity for clarity.
• Assuming ‘I guess’ means they agree with you — it often means the opposite.

Helpful Tips for Handling the Moment

• Pause and listen to tone and body language; ‘I guess’ might mask hesitation, sarcasm, or fatigue.
• Ask an open-ended follow-up rather than a yes/no question to invite detail.
• Offer space if they need it: ‘If you want time to think, that’s fine — we can come back to this.’
• Reflect back what you heard: ‘So it sounds like you’re leaning toward X but not fully sure, is that right?’
• Keep your own response calm and nonjudgmental to encourage honest sharing.

A Note About This Particular Situation

Context changes what ‘I guess’ means: in a workplace it may signal uncertainty about task expectations, while with a friend it might be emotional caution. Pay attention to power dynamics — people are more likely to hedge when they feel vulnerable or fear disagreement. When in doubt, steady curiosity is usually the kinder choice.

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.