Softball Questions to Ask
Low stakes questions for the first few minutes with someone new, when the aim is comfort rather than depth. Each note says what the answer tends to give you and where to take it next.
The questions
Open any question for the note
Do you have any pets?
Why ask it
The most reliable opener in the list, because owners will talk about an animal for a while with no self consciousness at all. If the answer is no, follow with whether they grew up with any, since almost everyone has a story either way.
What is your usual coffee or tea order?
Why ask it
Answers arrive fast and often come with a small confession about a habit, which is a friendlier start than a preference question. It also gives you something practical to remember if you end up making a drink for them later.
Are you a morning person or a night owl?
Why ask it
A two option question is easier to field than an open one, which makes it useful with someone visibly nervous. Follow with what time they actually get up, because the gap between the identity and the alarm clock is usually the funny part.
What did you get up to last weekend?
Why ask it
Better than asking how they like to spend weekends, because a real weekend produces real detail while the general version produces an ideal. If the answer is nothing, say what you did and it usually loosens something up.
What is the best thing you have eaten recently?
Why ask it
Naming one recent meal is easier than picking a favorite food, and the answer often includes who they ate it with. Watch for a home cooked answer versus a restaurant answer, since each leads somewhere different.
Do you cook much, or is it mostly takeout?
Why ask it
Neutral enough that neither answer feels like a judgment, and it quietly tells you how much time someone has. Cooks will usually name their one reliable dish if you ask, which is a good thing to know about a person.
What is the last show you actually finished?
Why ask it
Adding actually finished is what saves this from the usual dead end, because it rules out the polite list of things people mean to watch. If you have not seen it, ask what made them keep going rather than what it is about.
Beach or mountains?
Why ask it
Almost everyone has an instant answer, and the reason behind it usually leads to a specific trip. Keep it as a follow-up rather than an opener, since a bare either or question can feel like a quiz if it lands first.
Are you a planner, or do you tend to wing it?
Why ask it
It gets at temperament while sounding like small talk, and both answers are ones people are happy to claim. Ask for the last time it worked out badly and you will usually get a story.
What is your favorite time of year where you live?
Why ask it
Tying it to where they live makes it more specific than asking about a favorite season, and it often surfaces where they grew up. It also works with someone you have nothing in common with, since everyone experiences the weather.
Do you listen to anything on your commute?
Why ask it
More productive than asking about favorite music, because it gets a concrete answer: a podcast, a particular album, or silence. Silence is an interesting answer too, and worth asking about rather than moving past.
City or small town, if you had the choice?
Why ask it
Light on the surface but it usually brings out where someone has lived and what they thought of it. If they hesitate, the hesitation itself often introduces a move they are currently thinking about.
How do you unwind after a long day?
Why ask it
Slightly more personal than the questions above it, which is why it belongs here rather than at the start. Answers about a specific ritual, such as a walk or a particular chair, are more revealing than answers about relaxing in general.
Do you do anything to stay active?
Why ask it
Phrased with anything so that a no is comfortable, since a question assuming a gym routine can land badly. If they do have something, ask how they got into it, which is more interesting than how often they go.
Do you like working around other people, or do you need quiet?
Why ask it
Practical if you might end up sharing a space, and safer than asking about their job. It also gives you an easy read on how much of the current conversation is costing them.
Are you a saver or a spender?
Why ask it
Light enough to stay in softball territory as long as you keep it to the label and away from amounts. Most people answer with a self deprecating example, which is a good sign the conversation has warmed up.
Have you bought anything small recently that you would recommend?
Why ask it
This gets people genuinely enthusiastic about something mundane, which is a better trade than another preference question. It is also one of the few small talk questions where you leave with something useful.
Do you have a favorite holiday?
Why ask it
Answers often bring in family, food, or a tradition without you having to ask about family directly. Be ready for a flat answer, since holidays are complicated for plenty of people, and move on easily if so.
What did you want to be when you were a kid?
Why ask it
Nostalgic rather than probing, so it stays comfortable while producing something more memorable than a preference. The follow-up worth asking is whether any part of that turned out to be true.
Is there anything you are looking forward to in the next few months?
Why ask it
A good closer, because it ends on something positive and often gives you a reason to speak again. If nothing comes to mind, that is a perfectly normal answer, and asking what they wish were coming up works as a gentler version.
Using Easy Questions Well
Practical guidance for the conversation itself
Making Small Talk Go Somewhere
The follow-up is the point
A softball question is not meant to be interesting on its own; it is meant to produce something you can ask about. Pets, meals, and weekends are all launch pads. If you take the first answer and move to a new topic, you get a survey rather than a conversation.
Answer your own question briefly
Two sentences about your own weekend or your own pet sets the length you are asking for and stops the exchange feeling one sided. Long answers do the opposite and hand the other person a listening job.
Read the two word answer
If someone gives you a clipped reply twice in a row, the topic is not landing or they do not want to talk right now. Change subject once. If it happens again, let the conversation rest rather than working harder at it.
Prefer recent over favorite
What did you eat this week gets a real answer; what is your favorite food gets a stalled one, because people feel they should pick something impressive. Anchoring to the last few days removes that pressure and produces detail.
Know when to stop using them
Softballs are for the first ten minutes, a large group, or someone who is clearly uncomfortable. Past that they start to feel evasive, and the other person is usually waiting for you to ask something with a bit more substance.
How These Go Wrong
Firing them off in sequence
Four preference questions in a row is an interview. Space them with your own answers and with ordinary comments about what is happening around you.
Questions that assume a life
Asking about their gym routine, their kids, or their partner is not a softball if the assumption is wrong. Phrase it so that no is an easy answer: do you do anything to stay active, rather than where do you work out.
Treating light as meaningless
People do reveal a lot in these answers, so listen properly rather than waiting for your turn. The point of an easy question is that it is easy to answer, not that the answer does not matter.
Pushing a topic that visibly cooled
Holidays, family, and hometowns are safe for most people and not for everyone. If the temperature drops, do not ask a clarifying question; move on and come back to something neutral.