The Best First Date Questions — Plus What to Avoid Talking About
A therapist shares the best questions to determine compatibility.
DEAR DR. JENN,
I am dipping my toe back into the dating pool, and I'm worried about keeping the conversation flowing. I don't love small talk, but I know the conventional wisdom is to stay away from heavier topics like politics and religion — but what else is there to talk about? And if I'm looking for someone I'm truly compatible with, isn't it important to know how they feel about these deeper topics? What should I even ask on a first date these days? —Tongue-Tied
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DEAR TONGUE-TIED,
Your priorities in life and criteria for a mate may change at different points in your life, especially if you are ready to find someone you are truly compatible with. So while you're right that heavy topics don’t lend themselves to a light and fun first date, many singles are prioritizing political beliefs and social justice issues when picking a partner — which means they're important to discuss early on so that you don't waste your time with someone you aren't compatible with.
In my experience, clinical and personal, people are at their most honest on a first date. According to research by psychologist Arthur Aron, a key pattern associated with the development of a close relationship is “sustained, escalating, reciprocal personal self-disclosure.” In other words, to become and remain close, we must be open and forthcoming about our inner world. That said, you don’t want to reveal too much personal information too soon. The development of intimacy while dating should be gradual. If or are looking for a meaningful relationship, talking and getting to know each other over time is the best way to do that.
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Before spilling your heart on the heavy stuff, the typical first date questions can be a good way to lead in. According to dating expert Patti Stanger, (whom you may know from Bravo's Millionaire Matchmaker), one of the most important things to determine on a first date is if this person is someone you click with. You can ask fun, light questions about things like travel, food, hotels, restaurants, and preferences to get a sense of whether or not you are on the same page, share the same interests, and find each other intellectually stimulating.
If you are going to talk about issues such as abortion rights or your political view on a first date, you may want to start with more broad concepts to rule out someone who is diametrically opposed to your views, but save the more detailed conversation for another date or two.
Looking for other topics to talk about on a first date to help you ease in and get to know your partner better? Start here:
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Travel
A study by psychologist Richard Wiseman found that talking about travel is a very successful dating topic. According to his research, couples who talked about travel wanted a second date 18 percent of the time, whereas those who talked about movies only wanted a second date 9 percent of the time. Think about it: Movie conversations can get a little argumentative, while conversations about past adventures and exciting travels tend to make people seem more attractive to one another. A few fun questions to ask about travel are:
What amazing adventures have you been on?
What is the best vacation you’ve ever been on?
Where is a place you have always wanted to go to but have never been?
What place have you traveled to that was better than you expected?
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Passions
As Stanger points out, people tend to feel good when they talk about things they are passionate about — and in turn, feel good about their date. Asking questions about the things in their life that spark joy allows you to learn about your date and to see if your interests and values align. Some questions, along these lines, that you could ask are:
Are you working on any passion projects right now?
What's your favorite way to spend your free time?
Who is the most fascinating person you’ve met?
What hobbies would you get into if you had unlimited time and money?
What new skills have you learned or activities have you done recently?
What are you always game to do?
What is the most spontaneous thing you’ve ever done?
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Entertainment
Entertainment-related topics are always a fun way to connect. They allow you to see if you have the same taste and intellectual interests, and they may even turn you on to something that you hadn't heard about.
What was the last book you really got into?
What TV series do you keep coming back to you and re-watching?
What was the last show you binge-watched?
What are your favorite apps on your phone?
What are your favorite podcasts?
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Career and Lifestyle
Getting a bird’s-eye view of what a day in the life of your date typically looks like can help you figure out if you are compatible. If the idea of peeing in the woods makes you want to scream and your date loves to spend weekends camping, it's probably not going to be a match. If you were constantly getting annoyed at your last S.O. because she worked too much, finding out about your trauma surgeon date’s 80-hour workweek in advance can save you a lot of heartache. Some simple lifestyle compatibility questions you can ask are:
What is a typical workday like for you?
What about the weekends?
What is the most surprising thing that happened to you in the past week?
What drew you to your work?
Are you a morning person or a night owl?
What is your most important outlet to help you de-stress?
How much alone time do you tend to need?
Which do you prefer, big parties or small gatherings?
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Family, Friends, and Upbringing
We can learn a lot about a person from the company they keep. The atmosphere we grew up in, our parents and siblings leave a lasting impression, so learning about those people in your date's life will give you valuable information. Also, social preferences, comforts, and discomforts can be very telling. Some questions you can ask in this area are:
Who are your closest friends and why?
What friendships have impacted you the most?
What was your relationship like with your parents growing up?
How close are you with them today (do you talk on the phone once a day, once a month)?
Where did you grow up?
How would your friends and family describe you as a kid? In high school?
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Relationship Goals and Priorities
When looking for a long-term partner, you want to find out if the person at the table with you is looking for the same. It is also important to find out their views on relationships. In this day and age, you should never assume that person you are on a date with wants monogamy. These are important questions to ask to help you find out about your date's relationship history and get a sense of what they're looking for in the future:
What are you looking for in a relationship?
What are your thoughts on monogamy?
Do you see yourself getting married?
If divorced, how did you like being married?
How long have you been single?
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Religion and Politics
While we always hear that we should avoid talking about politics and religion, if you’re looking to spend your life with someone and these issues are important to you, you are going to want to touch on them during that first date. I recommend asking questions that will give you a sense of how your date feels about issues that are important to you, without getting too intense and argumentative.
What religion were you raised in?
Is that religion still part of your life?
Do you consider yourself to be spiritual?
How do you feel about the upcoming election?
Have you ever had politics or religion end a relationship that was important to you?
Have you ever been to a protest or a rally?
What social justice issues are you most passionate about?
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First Date Don'ts
Here are a few topics that you should avoid on a first date — plus general tips for making the best impression.
Don’t ignore the red flags.
According to Stanger, the two biggest reasons why women ignore red flags are because they are super attracted to their date or because they have already created the fantasy of the marriage they plan to have with this person. Keep your eyes wide open no matter how hot someone is.
Stay away from sex.
Sex is super important in a relationship — after you get to know each other. Once you're with someone, understanding their preferences (and vice-versa) is super important, but you do not need to find this out on a first date. If you spend a lot of time talking about sex, you are not going to be getting to know each other intellectually and emotionally, which should be your focus on date one. And if your date pressures you to take things physical before you're comfortable, that is a red flag.
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Don’t talk money.
Sure, you want to make sure that the person in front of you is a hard worker or has the same priorities about saving as you do, but there are ways to go about this. Offering to split the bill if you are doing a dinner date, or seeing what they offer/suggest when it's payment time should tell you more about your compatibility than asking how much they're taking home.
Throw away your checklist.
Stanger says she sees too many women with a vision of what their future husband will look like on paper — so they rule out great men who don't have everything on the list. For example, you may want to reconsider how much weight you place on a specific college degree or a physical attribute like height.
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Avoid yes or no questions.
Always ask open-ended questions. Yes or no questions tend to hit a brick wall pretty fast, while open-ended ones allow the conversation to keep flowing, even if either of you is nervous.
Skip the pick-up lines.
Cheesy pick-up lines do not work. This is especially important for men to know. Most women have heard them all, and they’re so generic that they do not make the receiver feel special at all. I once went out on a blind date, way back before social media, and the guy greeted me by telling me that he had dreamt of me all night. The fact that he was wearing a whale tie and a fanny pack did not help his cause. Needless to say, it was a short date.
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De-stress before the date.
Take the time to clear your head and get relaxed before a date. If your boss yelled at you and you’re stressed out, you can’t stop obsessing about the pimple on your cheek, or you just had a fight with your mother, you will bring that energy into the date. Take the time to meditate, do some deep breathing, or whatever it takes for you to let the stress go. If you find that your self-esteem or how you feel about yourself is distracting you on the date, these are issues I'd recommend talking through with a therapist.
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At the end of the day, every single person that you go on a date with has something to teach you, enlighten you about, or share with you. Even if they don't turn into your life partner, it’s worth listening closely and paying attention. You could find out about something meaningful that will change your life, or something as small as a great new restaurant recommendation. All you have to do is ask.
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