Getting ready for a date can come with some nerves, especially if it’s with someone who has you particularly smitten. Maybe, it’s the first date, and you don’t know each other all too well, but you know that they’re cute and you’re interested. Perhaps, you’re a few dates in and want to know what questions to ask to see if this connection is worth continuing or not. Either way, having some questions on hand to ask someone on a date night is a great way to prepare.
Knowing what questions to ask on a date can ease your nerves and help you relieve or mitigate any potential awkward silences. Questions, after all, spark new conversations and keep existing conversations going, which tends to be a goal on dates. Talking about various topics, after all, is how you’ll know if you click. Alternatively, how you’ll know if you don’t. So, what are some good questions to keep in mind?
How To Choose The Right Questions
Depending on how much you’ve spoken already, the questions you ask might fit into different categories. You can come up with friendly questions, simple get-to-know-you questions, deeper love and romance-related questions, flirty questions, or quirky, silly questions to start. In other words, there are tons of thoughtful questions you can ask during this date.
How do you know which ones you should use? Of course, the questions you ask should be suitable for the length of time you’ve known the person, and they should also feel like relatively natural questions to ask. You might ask a question related to something you already know about your date, such as how they got into their line of work if you know a little bit about their career but don’t know the details, or pick a question that serves as more of an icebreaker.
From fun questions, philosophical questions to some great questions that will help you know more about their interests, hobbies, or future ambitions – you can make your date night a remarkable one and gauge whether this is someone you get along and are compatible with.
Questions For Date #1
If this is the first date, you probably want to start with a friendly question. You want to learn the basics about this person, but you don’t want to share information that could compromise your safety or ask something too personal within the first few minutes of seeing each other.
You can start with an open-ended and straightforward question such as:
At this point, you may want to switch the mood up a little with some unique asks. You can throw in some interesting questions like:
If you want to appear unpredictable and spontaneous, you may go ahead to ask him some deeper or more personal questions. Some deep questions which would seem like a sequel to the last light-hearted question could be some of the following:
Questions That Cover The Serious Stuff
Let’s say that you’re at a place with this person where you want to get down to business and learn if you’d work out long-term. That doesn’t mean that you want to rush into things. Instead, it’s that you don’t want to waste each other’s time. When you’re ready, here are some questions you might ask:
You might also ask some questions about family life. You do not want to build feelings for someone whose ideas and values on raising a family are far too different from yours. For example, if they’re set on having kids, and you don’t want them, that’s an essential base to cover. Differences in a partnership can be a great thing, but some things might be a no-go. Asking your date these important questions sets you up with the right information; if at all, you both proceed beyond the dating level. At this point, you can throw in a great question to find out if your family values align. Examples of such questions include:
What is your understanding of raising children?
Make sure to go with serious questions that fit your comfort level and theirs. When the time feels right, don’t hesitate to break it up with some light-hearted questions to keep things casual and fun.
Pop Culture Questions
Want to find some light-hearted common ground? At this point, you can throw in some exciting questions that are movie-related. You would discover it’s a fun question, and in fact, the question is great because they would most likely be in high spirits to discuss their favorite movie, especially if you are on the opposing end. Amazing questions like these can help you lighten up the place:
Questions that help you learn about a person’s music taste are a great idea, too! This could mean anything from asking if they remember a throwback hit or asking their favorite bands and artists.
Questions To Spice Things Up
Depending on what your connection is like, you might want to ask some flirty questions or sexy questions. Flirty doesn’t have to mean sexual or related to sex, but they can if that’s where you’re both at, and you have consent.
Some flirty questions you can ask are:
You can also ask flirty “truth or dare” questions. Only ask questions related to sex if it feels appropriate for the connection you have. Communicating about sex is extremely important because you need to know what each other like to have a good sex life. Still, it’s non-negotiable that this occurs when it is reasonable and respectful to ask.
Listening Matters, Too
It’s not just about asking the right questions. A vital element to hold in place during your conversation is your capacity to listen. You do not want them to feel you were absent-minded when they ask a question, and you tell them to repeat it because you were not listening. Of course, this will happen from time to time if you don’t hear what they say, but overall, listening matters. Though some forget, listening is, in fact, one of the most vital conversation skills, and it’s most certainly part of being a good date!
If your date seems uncomfortable with a question you ask at any time, it’s best not to press them. Especially if it’s a first or second date, remember that you also don’t have to share anything that crosses a personal boundary or that could be risky to share at this point in getting to know somebody. The ability to set boundaries and respect boundaries are both great signs and skills, and as your comfort grows, you can share more.
Whether you’re dipping your toes into dating, are in an ongoing partnership, or need help with something else that’s going on in life, counseling can help. You can get support from a counselor in person or use an online counseling platform. ReGain offers both individual counseling and counseling for couples, and all of the providers on the platform are licensed. Healthy relationships matter, romantic and platonic, so don’t be afraid to take the first step toward finding a professional to talk to today.
Frequently Asked Questions (FAQs)
What are interesting questions to ask a guy?
Here are some interesting questions to ask a guy:
Is there anything people assume about you that isn't true?
What do you wish people knew about you that they don't?
What's a topic you know a lot about?
What topic could you teach a college class on?
What are some fundamental pieces of who you are as a person?
Have you ever held a firm belief that changed? If so, what was it, and why did it change?
Asking interesting questions like the ones above will help you move past the standard hypothetical questions and get to know the questions many people ask someone they're interested in. They aren't invasive, but they'll help you get to know him better and will make him think!
What flirty questions to ask a guy you like?
Here are some flirty questions to ask a guy you like:
What's the most romantic thing you've ever heard?
What's the best relationship advice you've ever heard?
Is there anything you've always wanted to do for a date?
What would a perfect romantic evening look like to you?
Do you have any stories about yourself that'd surprise me?
You might also start a questions game, such as a trivia questions game or a game of 20 questions. If you choose a trivia questions game, pick a topic that you're both well-versed in! For example, if you share a love for horror films or rock music, you might pick a trivia game based on that.
What is a good personal question to ask a guy?
If you're ready to ask a guy what may be considered girlfriend questions or partner questions vs. get to know you questions, a deep question is a way to go. Here are some personal questions to consider asking:
What's one of the most challenging situations you've ever been in? What did it teach you?
What's the hardest lesson you've ever had to learn?
Are there any mistakes you've watched people in your life make that you learned from?
Who have you learned the most from in life?
What makes you feel good when you're down?
When were you the saddest/happiest you've ever been, and why?
Do you have any regrets?
Do you consider yourself a confident person?
What do you want to be remembered for?
If you're not sure if a question could potentially cross a boundary, or if you're not sure if he's in the headspace to be asked a specific question, consider checking it over first by saying, "I have a question, but it's personal. You can decline if you're uncomfortable. Is that okay?" That way, you'll have consent and will possibly avoid an awkward or uncomfortable situation.
How do you flirt with a guy over text?
Questions are great conversation starters. If you want to have a great conversation with a guy over text, ask him an interesting question. More specifically, ask an interesting open-ended question rather than a yes or no question. In addition to asking questions, you can flirt over text by using emojis, sending silly GIFs, memes, and photos, or you can text him to make plans. Even if it's a simple plan, such as asking him to get food or coffee with you, it's a way to gauge his interest and further your connection.
What are ten questions to ask?
Here are ten questions to ask someone if you haven't already:
What's the best part of your day?
Who is your best friend, and how did you meet that best friend?
Are there any skills or talents you wish you had that you don't have?
What's some of the best advice you've ever received?
What are some of your best memories?
What are your best and worst character traits?
What's on your bucket list?
What's the most unexpected thing about you?
Do you know your MBTI type?
Do you have any hidden talents?
Whether you're with your best friend or a person you're interested in romantically, asking questions is a perfect way to learn more about each other and have fun while doing it. If you're looking for a questions game to play, you might search the web for "questions question game" or "question games," but you can ask these at any time.