Dating Tips

Ask Your Date These Questions to Rock That First Date!

So you’ve finally scored a date with someone you met online–congratulations!

Hey, look — it’s perfectly alright if you’re feeling quite nervous. You’re human and that’s normal. And perhaps your date feels the same way too. No one’s spared from that ‘first date jitters’; relax, take a deep breath, and don’t be so hard on yourself.

But of course, nothing compares with the exciting feeling about finally meeting your match in the flesh, right?

Now, maybe you’re wondering: What sort of preparations should I make? 

For us, you should have a list of questions ready. Yes, that’s right — QUESTIONS! If you’d like to get the conversation going, asking your date interesting queries can do the trick. 

We’re not talking about those basic ones such as “what’s your favorite color?” and “what’s your hobby?” No, let’s get deeper than that. 

If you’re feeling too anxious to think about stuff you can ask your date, then maybe we can help you. Below is a list that might help spark the conversation. 

Who are the most important people in your life? 

most important people

Ask your date to tell you about their parents, grandparents, siblings, best friends, or even their pets. A perfect way to assess someone’s character is to pay close attention to how they answer questions and talk about other people. 

On top of that, it’ll also reveal which persons influenced them the most. It’s wonderful to see their eyes glisten while they tell stories about people that matter to them. 

Where’s your happy place? 

happy place

Your match might tell you about their favorite vacation destination or an awesome hiking trail. Or if you’re lucky, they might share about a secret place where they usually go to unwind, relax, and forget about the stresses of everyday life.

Through asking questions like this, you’ll know about the sort of place they’re comfortable with.

What’s your most embarrassing experience?

embarrassing moments

Now, let’s see if they’re comfortable enough to share with you some of their embarrassing moments. When someone tells you about awkward situations they’ve been to, it shows their humility and sense of humor. 

And of course, it’d be nice to have some light conversation and laugh every once in a while during your date.

What bugs you the most?

Pet peeves

We all have pet peeves which means your match is not an exception. Start a conversation about stuff that gets on your nerves and let your date tell you what bothers him as well. 

If you learn about these things on the first date, you’d know what makes them tick and can avoid it in the future. Well, that is, if both of you decide to take your relationship to the next level. 

What’s your favorite joke?

laughing at jokes

Who doesn’t love a great sense of humor? Almost everyone finds funny people irresistible— who knows? You may have the same kind of humor and even exchange witty banters. 

To do this, you can ask them about things or jokes that made them laugh. 

Moreover, laughing together at stupid “dad jokes” can help break the ice and make you comfortable with each other. 

Would you rather…?

would you rather

‘Would you rather’ questions can be very useful on the first date. 

Aside from breaking the ice, the questions can also be answered by both of you. It can be something deep or silly, depending on the flow of your conversation. 

For instance, you can ask them questions like: Would you rather… go to the mountains or the beach? Drink beer or tea for the rest of your life? So yeah, whatever you can think of–get creative!

What’s the scariest thing you’ve done?

overcome struggles

Instead of nosing into confidential details about their life like failures and heartaches, why not ask them about the most challenging thing they’ve done. Learn about their struggles and how they’ve overcome those. 

You’ll get all sorts of answers. And if you get a fun response, don’t forget to appreciate the strength they showed in surviving things that exposed their weakness. 

What’s on your bucket list?

With this query, your date will have the freedom to share with you about their interests and dreams

Their list might include career goals, adrenaline-junkie adventures, travel plans, and personal milestones. Or maybe they’re planning to try some exotic foods like escargots. 

Here’s our final say

Now that you have your questions, we have one last tip for you — have a balanced conversation. It means that both of you should have equal chances to talk.  So yeah — that’s how you rock your first date.

If you’re into matured women, you can check out the best MILF dating sites on the Web to meet your ideal match.

Still feeling nervous? Well, at least you’re now armed to the teeth with these questions and have fun!