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The image features two hands holding each other on their first date in a open garden.

5 First Date Questions That Aren’t Boring AF

Posted on April 4, 2025January 6, 2026 by official.honeynhugs@gmail.com

Is there anything more mortifying than a first date? Well, as nerve-wracking as it may feel, meeting your potential partner for the first time can be full of butterflies (or, maybe icks, sometimes). But, if you wanna know that cutie without being a bit too intrusive, the best way is to………well, ask questions!

Fact time- did you know that people are always attracted to confident people? (as said by a relationship expert who literally holds a PhD!) Asking good questions can make you feel confident. And, given the 2025 dating field, we want you to know the guy before we fall for them.

But, always remember- a first date should never feel like an interview. Yes, it can be hard to put your thoughts in question, but the key here is feeling relaxed. And, if you already feel relaxed with someone on your first date, that’s a huge green flag (speaking from personal experience).

The point is, to create a natural convo with your potential partner, you need a mix of everything fun, goofy, and definitely some chemistry. So, here are some 5 first date questions that do NOT suck.

PS- if you are looking for some date ideas, we have a list here.

What made you ask me out on a date?

Okay, asking “Do you like me?” is definitely a convo-ender. But, an open-ended question like What interests you about me is definitely worth the shot. This would actually help me understand what the intentions are. Plus, if you know what sparked interest in them, you feel naturally more confident. And, this question is also a little flirty, so you would know if you have that chemistry.

What are you looking for?

Okay, personally, who wants to waste time? If you are struggling with what to talk about on a first date, talk about your expectations. And, apart from getting to know the expectations, this question is actually a good way to spot red flags. If they are straight-up honest about it and know what they want, then that’s good talk. But, if they are defensive about it- well, then, you already deserve better.

How do you chill?

Asking hobbies on a first date is like taking an interview while sipping cocktails. So, put it down a notch. You can talk about the things you like to do, allowing them to fill up your conversation. Remember, it can be hard to break the ice, but if you guys are really vibing, you will get through it.

How’s your work life?

This is a cooler version of “Do you know how to manage work-life, or are you just stuck deep in corporate?” A healthy relationship, casual or serious, is always about balance. And, if you are seeing a potential future with them, this first date question will help you know if they actually have time for something so serious.

What you do on weekends?

Well, honestly, rot in bed, while watching something from Netflix’s My List. But, this can actually be a great conversation starter. You can find out if they are a gym freak or have a travel bug in them. This might also give you a common ground to talk more about. And, finally, you won’t be wondering what to do on your first date (or, second one, perhaps).

Here are some dating advice for someone you meet online.

Category: Dating

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