Questions You Should Never Ask on a First Date (and What to Ask Instead)
I wouldn’t call a first date an “interview.” At the same time, some valuable interview tips and tricks can also increase your chances of a successful first date. You want to do your best, make the conversation natural, and get important information about the person sitting across from you.
Think back to your last job interview. It was probably much easier for you to answer a specific question, such as “Could you tell me about a time when you overcame a difficult situation at work?” over the vague, unfinished, oh-so horror of “tell me about yourself.”
In any context, the last question is too broad to start a meaningful conversation. Every time I feel connected on a first date, it’s because we organically discover that we both love the same episode of the same show, or we think a certain musician is overrated, or we want to become regulars on the same same restaurant. I never felt a spark after someone asked if I’m “passionate” or “I care about honesty.” So many well-intentioned first date questions turn out to be too vague or boring, or both.
So what is one person to do? Luckily, compared to your only chance to get a quality response on apps , you have a lot more leeway to start a conversation when you’re in front of a real, live person. But just like with apps, all the best questions you can ask should be specific, original, and personalized. And given the classic first date pressure to fill every minute of silence, you won’t regret it if you have questions ready. So here are some terrible questions you should avoid on a first date and what you should ask instead.
Avoid these questions on the first date
I’ll give you the benefit of the doubt and assume that you don’t even think about questions like “how much do you weigh?” or “Do you think you could overtake me?” or “Can you babysit my cat this weekend?” Instead, I’m guessing you mean well, but are struggling to spark a conversation when meeting someone new. The following questions are well-intentioned but so boring or so irrelevant that your companion is likely to start planning his escape.
- “So what’s your story?” These are romantic “tell me about yourself” activities. Not only is it impersonal, but it’s so overt that you don’t give your partner a meaningful opportunity to respond to it. A good first date will give you something to work with as a follow up, but you better be specific and original after you fail that first date.
- Why are you still alone? Some people try to turn it into a pickup, a compliment, or something like that. (“You’re so cool… how are you still single?”) Even if you’re trying to be flirtatious, think logically about how it ends. The other person may respond shyly, “Oh, who can say…”, but inwardly they think about how ambiguous your “compliment” seems. Now they are struggling to steer the conversation away from why they are truly single, such as their deep-seated commitment issues. Or worse, you have now opened the door for them to steer the conversation towards their deep-rooted commitment issues.
- – What attracted you to me? Another unsuccessful attempt at flirting. This question, in particular, will sound either too arrogant or too uncertain. In any case, do not chase after compliments.
- “What are your hobbies?” Too general. Ideally, they should casually hint at one of their hobbies in the conversation, or you’ll be a bit knowledgeable in the conversation. From there, ask specific questions about how, when, and why they do what they do.
- ” What is your family like?” I find family talk to be fair (and often exciting) first date territory. However, you must personalize it. If you feel confident, you can try to guess if he is the middle child, or you can ask them if they are close to their parents. Avoid “did you cause your parents to divorce?” or “why don’t you talk to your father?” Keep it light.
- “Red or white wine?” Red. You? White? Chill. Great conversation.
Instead, try asking these questions on a first date.
Here are some ideas to think about if you really want to know your date. The main thing is that the other person feels comfortable and interesting. By supporting them, you simultaneously distinguish yourself as an original, confident and attentive person.
- “Which holiday is the best, without a doubt?” Strong stances are important if you keep them low stakes and playful. With the best holiday question, you can open the door to learning about their family, traditions, favorite season, food preferences, not to mention their overall creativity with the answer. Questions like these are perfect for flirtatious banter.
- “What were you like as a kid?” This gives the other person the opportunity to talk about themselves and their personality, but with a little more distance than if you directly asked them to describe themselves right now.
- “Would you rather…” The “would you rather” prompt is perfect for showing off some personality without having to reveal too much personal information too soon. Such questions can be innocent, flirtatious, deep, or whatever. For example: “Would you rather sleep with your closest friend or your worst enemy?” or “would you rather read minds (but you can never turn it off) or become invisible for one day a year?”
- “What did you do today?” Yes, I know it seems elementary. I know it seems like I’m going against my own advice to always be specific. It is extremely important that you remain normal . If your first question when meeting a guy is “would you rather…”, you risk coming across as ostentatiously quirky. You still need these types of questions to find out what the other person is like, what they like to talk about, and to make sure both of you are comfortable getting to the bottom of things. Plus: “What did you do today?” even more specific and fruitful than the open-ended question “how was your day?” Takeaway: Don’t be too harsh (“ranch or blue cheese?”) without first talking about general pleasantries.
- “If you had 24 hours to do whatever you want, what would you do?” It’s stupid and inventive, gives a lot of room to move back and forth, and it tells a lot about human priorities, imagination and shit.
- “Who did you vote for?” Difficult, but saves time.
Conclusion: be interesting, but be yourself
Unfortunately, the most important part of a first date is figuring out how to be yourself. My advice to choosing questions that are specific and original makes sense, but it cannot replace the most natural flow of the conversation. Well thought out questions are a good start, but a date should n’t feel like a job interview or interrogation either.