Questions to Ask in a New Relationship

The best questions for a new girlfriend are the ones that show you how she lives, how she handles trouble and what she wants from this. Ask them one at a time, spread across a few weeks, while you walk or eat, and share your own answer after hers. A list read out in order feels like an interview, and she will answer like one.

Give a little before you take a little. Ask the question, then answer it yourself in a sentence or two so it feels like a conversation. Keep it playful. "What do you do when you're annoyed at someone close to you? I go quiet and work out, which my friends find irritating."

a dating coach coaches the same move in conversation: when a question is awkward to answer, turn it around and let the other person explain. That works in both directions, so when she asks you something heavy, you can hand it back with "I have an answer, but I want yours first."

Do not ask more than one or two real questions in a stretch. Mix them with stories, teasing and silence.

These tell you who she is on a plain Wednesday.

• What does a normal week look like for you?
• What do you do to recharge after a bad day?
• Who do you call first when something great happens?
• What are you doing in your life that you are proud of and almost nobody knows?

Listen for what she lights up about and who she mentions. A woman with close friends and a life of her own is usually easier to be with than one who has organized everything around dating.

You learn more from trouble than from good days.

• What do you do when you're upset with someone?
• What is something you needed to apologize for and did?
• What do you need from a partner on a hard day: space, company, help?
• What is the last thing you changed your mind about?

Pay attention to how she describes people who have wronged her. If every story has a villain and she plays no part, notice that. If she says "I could have handled that better", that is a good sign.

This is the group men avoid, and it is the one that saves months.

• What do you want your life to look like in two years?
• What are you looking for from this?
• How do you feel about seeing other people while we figure that out?
• How important are kids, marriage and where you live?

coach teaches starting with the end in mind: know what you want from a relationship and say it early, because the way you act in the first weeks sets the terms. If you want to be exclusive, ask about it by the third or fourth date and say your view first.

coach says he is not a big fan of talking about exes in the early weeks, though he will tease a woman about what she brings up. Take that approach. One question is enough: "What did your last relationship teach you?" Let her answer in her own time, and do not ask for details or compare yourself to him.

Do not trade lists of exes or numbers. It rarely helps anyone.

The most useful questions are about you.

• Do I feel more like myself around her, or less?
• Is the time we actually spend together good, or do I just like how she looks on paper? coach names this trap: choosing by resume instead of by what an ordinary Tuesday with her is like.
• Do I feel respected?
• Would I want her if she were not what my friends envy?

If you keep answering these with a flinch, no list of questions to her will fix it.

Specific answers beat clever ones. "I want to move back near my sister in two years" tells you more than "I want to travel and be happy". Notice whether she asks you questions back, because a woman who is interested wants to know you too. Notice whether her words and actions match, and whether she can be honest without being asked twice.

If her answers and yours point in different directions on something you care about, such as kids, location or monogamy, believe it now. It will not get easier to hear later.