Pro Tips Link Copied 02.14.24

35 Questions That’ll Take Your Dates to the Next Level

Go deep without feeling weird. ByAlyssa “Lia” Mancao, LCSW

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Let’s just state the obvious: Going on dates—whether it’s the first or fifth—can be awkward, uncomfortable, and anxiety-provoking. If you’re not sitting in complete silence or getting hit with the ick, you’re tempted to launch a full-on inquisition or resort to random first date questions like, “So, uh, do you like cheese?” (“My favorite’s Gouda,” —IYKYK) 

Listen, dating can be fun, but it can also be confusing and exhausting. You’re usually meeting a stranger and trying to make the convo flow while battling thoughts like, Will they like me? Will I like them? Are they going to ask me to split the bill? Does this ever get easier? 

For some, you might even feel so uncertain that you avoid getting into the topics that matter because you want to come across as chill or “someone who doesn’t take themselves too seriously.” Unfortunately for all of us, that’s a recipe for getting stuck in situationships, JFYI. 

As a licensed psychotherapist with over 10 years of experience guiding folks through a range of relationship and dating concerns, I know none of us are doomed to be awkward or avoidant daters forever. Becoming more comfortable starts with having a conversation roadmap that includes which questions to ask, when to ask them, and how to ask them. To help you do exactly that before your next rendezvous, here are 35 Qs you can use to steer any convo. 

A few reminders before you save all these in your Notes app:

• Don’t fire them off like a job interview; pick the ones most important to you and weave them into your date using whatever language feels natural.
• If you struggle to keep the chat flowing, it’s OK to bring up something else by saying, “I have a question.”
• You should expect to respond to any “what about you?” follow-ups.  

Start with the basics. 

It’s important for both people to ease into a first date and feel comfortable with one another before unpacking trauma, for example. Skip the hard-hitting asks for now and focus on icebreakers that keep things light-hearted and offer clarity on your common interests. These introductory Qs are also a solid opportunity for you to see if they have a good sense of humor, can make polite conversation, and are curious about you too. All! Important! Things! 

1. What type of music do you like, and what’s the last concert you went to?
2. When you travel, do you like to have a packed itinerary for max efficiency or do you prefer a chill vibe with flexible plans? 
3. What’s one thing you’re looking forward to doing this year?
4. What are your top three favorite TV shows of all time?
5. What does a typical weekend look like for you? 

Get to know their values. 

One of the most common mistakes is overemphasizing chemistry and equating it with compatibility. In my experience, people often think that intense attraction or random coincidences (like having the same birthday) are signs that someone is their lobster. The dangerous part of that is developing a premature emotional and psychological attachment to someone you don’t really know. (This can make red flags harder to spot.) 

Meanwhile, true compatibility takes time to assess and unfold. Matching with someone would look like your values and long-term goals aligning, healthily navigating conflict together, and co-existing in the same living space. Figuring this out takes time. 

Truth is, we need chemistry and compatibility. While you can generally tell if the vibes are off the charts, determining if someone’s a good fit for you comes from weathering life’s ups and downs and asking lots of questions. Feel free to borrow any of these, and make sure you pay attention to their actions to make sure they’re consistent with the things they say.  

1. What qualities do you value in a romantic relationship?
2. How important is _____ to you? 
3. What’s your preference on paying at the end of a date?
4. If you had the power to address any cause or social issue, which one would you choose?
5. What role do your family and friends play in your life? Do you have a close relationship with them? 
6. Who would you consider your support system?
7. What’s your approach to finding work-life balance? Is that important to you? 

Dive into their past. 

Naturally, when you’re building a relationship, you want to learn everything there is to know about someone’s dating history or lack thereof because it gives you intel on their romantic patterns. Like, if they have a strong sexual attraction to a specific demographic based on some stereotypes, there could be some concerning fetishization going on there. Or if they have a track record of cheating, proceed with extreme caution. 

Unpacking someone’s past can also provide insight into where they’re at in their mental health journey. For instance, if they previously avoided dating altogether, you can learn more about what internal work they’ve done to get to this date with you.  

Of course, talking about the past and exes can be touchy. If you want to go deep on the first date, read the room and make sure the ice is fully broken before you dive in. Approaching these questions with a sensitive tone and adding the disclaimer “feel free to share as much as you’re comfortable with” is a thoughtful way to go.

1. Have you ever been in a serious relationship?
2. What’s the longest relationship you’ve been in?
3. Why did your last relationship end?
4. What’s your perspective on exes remaining friends after a breakup? Are you friends with any of your exes?
5. What’s something you’ve learned about yourself during your single years or from your last relationship? 
6. What are you looking for based on the relationships that you’ve been in or your time being single? 
7. What’s something that often triggered you in your previous relationships?
8. What do all your exes or crushes have in common? What do you think attracts you to them? 

Start the communication conversation. 

Communication is one of the core foundations of a healthy relationship, and knowing how someone conveys their thoughts can help you decide if a relationship with them is worth it. If you’re a talker who loves chatting on the phone while they prefer to limit communication until they see you IRL, you’ll likely end up feeling lonely. And I don’t want that for you! Remember to sprinkle in these questions to ensure you’re on the same page (and, again, see if their behaviors match their words).

1. Are you more of a texter or a caller? 
2. How do you show your appreciation in a relationship? How do you want your partner to show that they appreciate you?
3. How do you typically respond if something is bothering you? Say something? Get quiet? Ask for space? Process the situation for a while?
4. In the beginning of any relationship, how often do you like to talk to the person you’re getting to know?
5. What are your views on gender roles and their stereotypes? Do you feel that one person should take the lead in the relationship more in certain areas or that the relationship should be more collaborative? 

Sus out their intentions. 

Ideally, by the second or third date you’d establish your expectations or any boundaries and get some clarity on the other person’s goals for this connection. Most people are afraid to ask the “what do you want” types of questions because they don't want to scare the other person. But if someone can’t give you an honest answer or takes this to mean you want to marry them on the second date, then this says more about them than you. To save yourself any wasted time or heartache, try to be direct early in the dating stage.  

1. What are you looking for? Something casual? Long-term? Lifelong? 
2. How would you describe your dating style? Do you tend to get to know one person at a time or multiple people at a time?
3. How long do you typically date someone before becoming exclusive?
4. What are your deal-breakers and non-negotiables for relationships?
5. What are your views on commitment, monogamy, or ethical non-monogamy? 

Cultivate intimacy. 

If you already have the basics down, like if you were friends first or have been dating for a bit, the questions you ask can go deeper. When you talk through these topics, they can help you develop more of a connection and a sense of vulnerability and intimacy with each other.

1. What is something I don’t already know about you?
2. What do you need to feel supported?
3. What are some goals you think we should have for our relationship, and why are those important to you?
4. What aspects of our friendship do you want to make sure is a staple in our relationship?
5. What helps you feel loved, safe, and protected in a romantic relationship?