20 Dating Questions That You NEED To Ask

Dating is difficult. It’s fun, it can be fulfilling, it is sharing energy, it is an experience every single time. From first dates that leave you with butterflies, to  dates that you barely remember the person’s name from across the table, even the dates that were so terrible you wonder what your ex is up too.

Dating has changed so much, nothing is really private anymore, people are live tweeting, group chatting, or making Tik Tok videos preparing for the date, or those who are on dating apps literally to talk about it on their fucking podcast. Dating is risky. And don’t get me a wrong, I live for it. My favorite viral videos are people imitating exes, or airing out dirty laundry of old hook ups. As someone who only shares her business, I am an avid supporter of the openness people have these days. But that doesn’t mean I don’t acknowledge that it makes dating and personal acts seem all the more…disingenuous. You run the risk of  fearing people’s motives and true interests for going out. Like are we dating because you want to get to know me, or are we dating so you can post about it on your blog that gets about 200 reads a month?

I hate when people hop into a relationship and they become relationship gurus and decide that they know everything there is to know about love. I mean honey who am I to talk? I spent at least 100 hours on Hinge and Tinder total, only to end up falling in love with my high school prom date. So, let me be clear, I do not know the answers, but I do have a couple of points on what to do when dating, and more importantly what to ask. My friend, let’s call her Caresha, is having a hot girl summer. Something I haven’t experienced since 2019, considering the fact that last summer I was depressed over an emotionally unavailable married man. And this year I’m out the game. It’s been a minute since I had a roster, sneaky link, or even been tricked on. So you could say occasionally I live vicariously through my friends. Caresha is living her best life. She’s always been beautiful, intelligent, outgoing, smart, the total package. But this post isn’t about Caresha, it is about her date we were getting ready for. Thursday night, Caresha was getting ready to go out to a cute little spot for dinner in the city. DC restaurants slap, I don’t care what anyone says. And I know that every social media mini influencer is going to shove RPM Italian and La Vie down your throat, but there is so much more than that. The dinner was a pop-up event, set with a pre fixe tasting menu, and a trendy décor. Caresha called me to ask what to wear, (I also had a pair of her jeans that I was holding hostage anyway.) I came by and as she scoured through crop tops and slides to go well with high waisted jeans, we discussed the guy: who he was, what he did for a living, how we thought he would dress, how he asked her to the date, do we split the check? (fuck no), how tall is he again?, and finally—what do we talk about?

I googled “first date questions” and here is the thing, for all the twitter think pieces there are about body counts, splitting rent, submissive women, when to have sex…there were very little useable questions I found on the internet for what to ask a person on a date. All of them were either too bland like ‘did you grow up with pets?’ or way to intense like ‘what are your thoughts on birth control in a relationship?’ and any decent ones I would have had to subscribe to the site, yea Cosmopolitan I’m talking about you boo. So I decided, to compile the top 20 questions to ask on a date. Why? Because I have been on so many dates, that I have mastered the art of asking someone about themselves. I have gone on dates with your typical dry IT guy with a lot of potential, your overly talkative club promoter who will absolutely  love himself more than you, the sweet ‘lost my virginity at 22 years old’ who works for a Think Tank guy, the ‘wow we flirted for so long and now were on this date and you’re… just okay’ guy, the eager to be a husband guy, the ‘our chemistry is so good but you’ll probably emotionally destroy me’ guy. Trust me you name the genre of man, and I have shared an appetizer with him. More importantly I learned how to learn people. I know how important it is to get to know someone, so you feel like your energy isn’t wasted. These 20 questions I share are full proof to get at least an hour worth of conversation that isn’t solely about work:

1.     What are three highlights from your day today?

2.     What is your family dynamic like: How many siblings do you have, are your parents together, do you feel like you had a happy childhood – what is your relationship like with your family members?

3.     What does friendship mean to you and what do you value the most in one?

4.     What is one of your favorite memories?

5.     Knowing what you currently know now, and that your presence wouldn’t change anything, what time period would you give to visit past or future? Be Specific (1950’s, 2030s?)

6.     If you could meet yourself – past, present, future version, what would you do? What are things you would talk about, what would you say? Are there any activities you would do?

7.     What do you do for a living? Is it something you’re passionate about?

8.     What are a few simple hobbies you have that give you peace?

9.     What are a few guilty pleasures you have?

10.  Do you travel, if so, where’s your favorite place you have been, (if not) where would you like to go?

11.  What are 3 pet peeves you have?

12.  Are you more of a morning person or an evening person?

13.  Super Embarrassing, when was your first kiss—how did it happen?

14.  If you could wear one item of clothing for the rest of your life what would it be? (if they don’t say black turtle neck it’s a red flag)

15.  What are your thoughts on the Lemonade Album? –you don’t need to be a stan to UNDERSTAND the importance of this

16.  If you were on a deserted island for a year, and you could only have these three items what would you bring? (in this scenario clean water, and some basic foods are provided)

17.  Are you more of a tv show or movies person, what’s something really good you recently watched?

18.  What are your genuine thoughts on social media apps?

19.  What does your ideal day look like – from 9am to 12 midnight?

20.  What are you looking for, in the dating scene? – ask this shit on the first date baby it is the biggest determiner on whether there will be a date #2

Let me know how it goes!

Xo

Ivana Estelle