In Hump Day, award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions — unjudged and unfiltered.

By Dr. Jenn Mann
Updated: May 01, 2019 @ 6:06 pm
Eva Hill

DEAR DR. JENN,

I'm out here trying to date — really I'm trying. And I know the conventional wisdom is to stay away from topics like politics and religion (and family drama, and...) when on a first date. But in "these times," what else is there to talk about? And if I'm looking for someone compatible with me, how can I figure out if we're a match if I can't ask about all of that important stuff? What questions can you ask on a first date that will help you weed out the weirdos, without being out of line? —Riddle Me This

DEAR RIDDLE,

In my experience, clinical and personal, people are at their most honest on a first date. And it may seem like a brain-teaser that you're supposed to be super forthcoming and extremely cagey at the same time, but it is what it is. That's why date interview skills are so tough to pin down — and don't get it twisted, a date very much is a job interview. (Hence all the rules, for instance: Don’t get too drunk.) According to research by psychologist Arthur Aron, a key pattern associated with 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.

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I spoke to Patti Stanger, author of Become Your Own Matchmaker: 8 Easy Steps for Attracting Your Own Mate and creator of the dating website Millionairesclub123.com (whom you may know as Bravo's Millionaire Matchmaker) and she said that one of the most important things to determine on a first date is if this person is on your level. 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. Ahead, our professional advice on what you can talk about on a first date to really get to know someone, and also have a good time. 

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. Movie conversations can get a little more 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 but have never been?

Passions

As Stanger points out, people tend to feel good when they talk about things they are passionate about. Asking questions about the things in their life that spark joy allows you to learn about them, and they start to associate those good feelings with being around you. This is seductive. Some questions, along these lines, that you could ask are:

• What do you like to do in 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 are some obscure things that you are or were really into?

• What are some things everyone should try at least once?

• What are you always game to do?

• What is the one thing that you have never done, that you always wanted to do?

• What is the most spontaneous thing you’ve ever done?

• Are you working on any passion projects right now?

• Are you into self-improvement?

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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Lifestyle

Getting a bird’s-eye view of what a day in the life of your date is 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 is 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 work week in advance can save you a lot of heartache. Some simple lifestyle compatibility questions you can ask are:

• What is a typical day like for you?

• What is the most surprising thing that happened to you in the past week?

• What drew you to your work?

• Are you are a morning person or night owl?

• What are your favorite weekend activities to relax?

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Family, Friends and Social Activities

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 kind of people?

• Who are your closest friends?

• Who, beside your parents, taught you the most about life?

• How much alone time do you tend to need?

• What were you like as a kid?

• Which do you prefer, big parties or small gatherings?

• What is your relationship with your parents like?

• Where did you grow up?

• Who cooked in your family?

Relationship

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 do you see yourself getting married?

• How did you like being married? (If married before)

• 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. Do not get into a debate about specific people in office, gun control, abortion, etc. Instead try to stay broad with open-ended questions. Try to get an overview of how he feels about the issues that are important to you without getting too intense and argumentative. Try to get in and out of these topics more quickly.

• What religion were you raised?

• 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 end a relationship that was important to you?

The Don'ts

Here are a few things that you should avoid on a first date.

Don’t ignore the red flags. According to Stanger, the two biggest reason 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 is a big part of the screening process. Sex talk tends to get us heated up and not syncing with our most intellectual parts. Save it for later!

Don’t talk money. Sure you want to make sure that the person in front of you isn't a slacker, but you don’t want to be tacky and ask how much they're taking home. This just makes you come across like a gold digger. Offering to split the bill, or seeing what they offer/suggest when it's payment time should tell you more about your compatibility than learning how much they make.

Don't stick to a checklist. Stanger says she sees too many women that have a vision of what their future husband will look like on paper and rule out great men because they don’t have something on the list. For example, you may want to reconsider how much weight you placed on a specific college degree.

Don't Ask 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.

Don't use pick up lines. Cheesy pickup 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 who had never seen a photograph of me or met me greeted me by telling me that he had dreamt of me all night. When I asked him what I looked like in his dream, he kept saying I was blurry. 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.

Don't go in off your game. 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 and that is not in your best interest. Take the time to clear your head, 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, consider getting some therapy to deal with that.

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 never know where you will 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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