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5 Questions You Should Always Ask On the First Date


With the prevalence of hook-ups in the age of Tinder and right swiping, sometimes the concept of love seems hard to fathom. However, for the collegiette looking for a serious partner, these are the five recommended questions that can be used to determine whether your first date could eventually lead into a long-term relationship.  

1. What was your childhood like?

From this question, you’ll get to understand the extent of parental influence on your date and gauge the state of their relationship with their family. Dr. Carole Lieberman, a Beverly Hills psychiatrist and author of Bad Boys: Why We Love Them, How to Live with Them and When to Leave Them, says that “the best predictor of whether a guy is a bad boy who will break your heart is his relationship with his mom. If he’s harboring resentments, he will take them out on you.” If your date relays miserable childhood stories and criticizes his upbringing, Lieberman advises that it’s best to avoid starting a relationship with them. 

2. What do you see yourself doing a few years from now? 

The benefit of having a conscientious and driven SO is that you’ll both inspire and support each other professionally. Olivia*, a junior at Seneca College, says that she doesn’t shy away from consulting her boyfriend for career-related advice. "He’s two years older than I am and has had more experience searching for internships and jobs," she says. "Whenever I needed help editing my resume or reaching out to recruiters, he’s always been there to offer tips and encourage me throughout the process."

Evidently, for a long-term partner, you want someone who knows what they want to achieve and the intent to follow through. During the date, other questions to explore could be asking about their short-term goals as well, how they lead to their overarching future plans and what motivates them to achieve them. After all, ambition is an attractive trait. 

Related:I'm 21-Years-Old and I'm in My First Relationship

3. What do you like to do when you’re not working?

You get a glimpse into their personality through the type of interests they have and can use this topic to see whether you share any common pastimes. Colin*, a senior at the University of Waterloo, concurs that finding common ground is helpful in getting your date to open up about themselves and gradually transition into other related topics. "I met this great girl last year who was really shy," he says. "I initially had a hard time maintaining a two-way conversation because she would try to deflect my questions. It wasn’t until I told her about my experiences studying abroad for exchange that she visibly relaxed and was more willing to talk about herself."

If you have a sense of adventure, you could ask your date whether they’ve traveled before, what cities they’ve been to and their most memorable experiences abroad. If you’re a cinema fanatic, you could ask what movies genres they enjoy, what films they’ve also seen and who their favorite characters are and why. If you have an appreciation for music, you could ask whether they play an instrument and what songs they’re familiar with. The possibilities are endless.

4. Have you read any good books recently?

While physical attraction is one component of maintaining a healthy relationship, intellectual stimulation is equally important. Elena*, a sophomore at Western University, says that being able to hold a friendly debate is her criteria for a second date. "It doesn’t matter what your view is on a subject, as long as we can have a fun and lively discussion, it shows me that you’re someone that isn’t afraid of banter and can hold their own," she says.

After the I-can’t-get-my-hands-off-of-you phase passes during the early stages of dating, you’ll find yourself bored if you and your love interest can’t hold an engaging conversation. During the first date, other questions to ask include what kind of books they’ve read in the past that they could recommend to you, who’s their favorite author and what’s their favorite novel and why. 

Related: 5 First-Date Mistakes You Don't Know You're Making

5. What are you most passionate about?

Through this question, you get a sense of what your date’s fundamental beliefs are and the humanitarian causes that they feel strongly about. Political views might be a bit of a sensitive subject for a first date, but topics such as whether they have volunteered before with a non-profit organization are safe if not encouraged. Jason*, a sophomore at York University, says that he likes to learn more about his date’s core values to determine their level of compatibility. "For me, I love seeing a girl getting fired up about a cause she really cares about," he says. "It’s honestly a turn-on because it shows that she’s the kind of person who has empathy for others and is willing put in the effort to help those in need."

While your date’s responses to these five questions will give you an idea about their character, it is also suggested that you be mindful of the following signs. Lieberman says that “you should pay attention to how much care he puts into planning your first date. If he’s hoping to have a serious relationship with you, he will have given your first date a lot of thought because he knows that if you have a great time, you will be more likely to agree to a second date.”

She says that how much your love interest spends is irrelevant because they could be creative and resourceful with planning the date (i.e. organizing a picnic at a scenic spot) regardless of whether or not they lack financial resources. Lieberman also notes that if they have the intent of taking you to their place for the first date then “he thinks you’re not worth the effort of planning something, and is hoping you’ll be fine with just hooking up.”

Evidently, finding someone who’s compatible with your personality isn’t easy. Sometimes, it’s like looking for a needle in a haystack. However, that doesn’t mean you can’t have fun. Regardless of how your date turns out, good or bad, going on a first date with different people lets you figure out what traits you like and also makes for great stories that you can regale friends with when you’ve had one too many glasses of wine.

*Names have been changed

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