These Second Date Questions are Guaranteed to Work

Yes, these are second date questions only. Why, you ask? They’re a little bit too intense for a first date, but deep enough to fit a second date. So, if you have no idea what to ask on a second date, you’ve found the right corner of the Internet.

I’ve taken several questions that are important to ask when you’re getting to know someone, and modified them for a date setting. Then, I’ll tell you exactly why you should ask that!

The goal here is to get to know the person in front of you without prying. You can do that with these second date questions.

Let’s get into it!

What Should You Talk About on the Second Date? Ask These Second Date Questions!

Second dates are weird because you’re not sure how much you can share without seeming like a creep. Don’t worry, these second date questions are the perfect balance of not too deep, but not too light either.

Question #1: What’s Your Biggest Goal in Life?

In this second date question, you’re asking your date about their aspirations and their dreams in life. You can gauge so many things from their answer, such as:

  • If they like to plan things or live in the moment;
  • If they’re realistic or big dreamers;
  • How much work and school means to them

By asking this question, you’re able to discuss both of your goals and see if they line up. Let’s face it, a big part of being compatible is having enough time to spend together.

Phrase it like that so it doesn’t sound like an interview.

If you word it like you would in a professional setting, like “what are your career aspirations?”, you might freak your date out and not get a third date!

If you ask what their ultimate goal in life is, they can answer in multiple ways, and aren’t pressured to talk about work and money. That’s a little bit too intense for a second date question!

Question #2: Are You Looking to Commit?

Second Date Red Flag

During this second date, both of you need to make it extremely clear about what your intentions are before the relationship progresses. This is important because you want to avoid anyone’s feelings getting hurt.

There’s no shame in wanting a more casual relationship, as long as you’re open about it to whoever you’re dating.

When you ask your date what they’re looking for, don’t tell them what you want just yet. Wait until they answer, and then tell them what you’re looking for.

Hear me out.

You might be on a date with someone who will tell you anything you want to hear just to be intimate with you.

To avoid that, let them answer first. Then, you can add to the conversation.

Don’t start a relationship with someone who doesn’t have the same intentions as you do. Someone will get hurt, no matter what you tell yourself.

Question #3: Tell Me About an Unpopular Opinion You Have.

Unpopular Opinions that are Red Flags

I have just given you the key to identifying creeps. This is the ultimate question to ask on a second date.

A lot of people pride themselves on having unpopular opinions on things. However, some opinions might be sexist, homophobic or just plain horrifying.

Listen to their unpopular opinion to see if they’re a creep.

If it makes sense and isn’t hateful, they’re not creepy.

If it degrades a group of people and they start rambling on about it, you may have a creep on your hands.

This is a question that would also be okay to ask on a first date, because it’s not super intrusive and it helps you weed out the bad dates.

Question #4: Tell Me About Something Cool That’s Happened Today.

Seems like a straightforward question to ask on a second date, right?

Now, let’s dig deeper and find out just what else your date’s answer tells you.

If your date answers bluntly and gives you a short answer, it could be that they’re shy. However, if you prompt them again and they still give you a one-word answer, you’re going to have a really rough second date (you’ll be doing all the talking!).

If your date gives you a negative answer, you’re dealing with a negative Nancy. You’re asking for something cool that happened to them, so if they give you a real bummer of a story, it’s time to dip. They’re most likely downers all the time.

You’re looking for someone to actually try to give you a positive and thoughtful answer. Even if they’ve had a bad day, they’re able to joke about it or find a silver lining.

You want that kind of positive energy in your life!

Question #5: What Weird Quirks Do You Have?

If you go on a bunch of second dates, you’re going to get weird answers to this question.

Essentially, you’re trying to figure out if your date is someone you can tolerate being around.

Are their quirks too much for you to handle? That’s up to you to decide once they answer your questions.


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    Question #6: What is Something You Could Talk About for Hours?

    This second date question is just plain cute. I want you to watch their eyes light up as they tell you about something they’re passionate about.

    It doesn’t matter if you have absolutely no idea what they’re talking about, but it’s adorable seeing people get excited about something.

    This is also a good second date question because it helps you find out how much chemistry you two have. If them getting excited makes you melt on the inside, you’re on the right track. If not, there might not be enough chemistry there.

    Just a warning: I really hope your date doesn’t talk about this one subject for hours. That would be horrible. If your date is a talker, you might want to ask this question at the end of the date.

    Question #7: How Would You Describe Your Personality?

    Second Date Toxic Traits

    This question is great for comparing your compatibility! If you’re a personality test junkie, you two could compare personality types or even take the tests together.

    If your date describes their personality, really listen to them. I mean it. Sometimes, we look at things with rose-coloured glasses, so we don’t realize that red flags are popping up.

    If your date describes themselves as:

    • A nice guy/girl
    • Someone clingy people are attracted to
    • Not like other guys/girls
    • Misunderstood
    • Fluent in sarcasm. Ugh.

    Those are all red flags. If you don’t want to see it in their Tinder bio, you don’t want them to actually describe themselves that way.

    Question #8: What Stereotype Did You Fit in High School?

    I like this second date question because you two get to talk about your personal growth since high school.

    It can also be fun to reminisce about that entire time period, or cringe together at the bad choices you made as teenagers.

    This question isn’t too deep, but it opens the conversation up to talking about your pasts, which is great!

    Question #9: What Did You Do During the Pandemic?

    2020 was rough. It’s almost comical, how awful the beginning of the decade was.

    It could be a good bonding moment to commiserate about how truly terrible the year was.

    A lot of people also used this time as a way to stimulate personal growth and change up their lives. You totally want to hear about that growth! It shows you their character.

    If this seems like a sore topic, move on. While this question can be great to bond, it might not be super great to pry if they don’t seem to want to talk about it.

    Question #10: What Do You Value in a Relationship?

    This second date question gives you a great insight on how they want a relationship to work.

    Before you go on the second date, ask yourself what you value in a relationship. Here are a few prompts to get your thoughts started:

    • How much do you value marriage?
    • Is having kids important to you?
    • Are traditional gender roles important to you or do you prefer a more modern approach?
    • What qualities do you want your partner to have?
    • What do you value most in life?

    Make sure that you two have similar values. They probably won’t change their minds on important things, so take what they say at face value.

    Question #11: Where Did You Grow Up?

    If you want to segue into talking about your respective childhoods, this is the question that will make that happen!

    It isn’t a kind of question that’s too forward, but it can lead to both of you talking about how your childhoods were and cute memories that you have.

    Plus, it’s a good way to find out if your date is family-oriented, which might be a value that’s important to you! You can get the sense if they’re family oriented if:

    • They talk about fun memories with their family
    • Their eyes light up when they talk about their home life

    You can also reminisce about your awkward phases in middle school (Mine was wearing an excessive amount of eyeliner).

    Question #12: What is Something That Makes You Unique?

    I don’t know about you, but I love finding the beauty in people. You can easily find the beauty in things that make people unique, like special talents or things that they’ve overcome.

    Even if your date tells you that something negative makes them unique, you can find the beauty in it! Here’s how:

    Focus on how your date’s life has been affected by this trait.

    Let’s say that you’re on a second date with a guy that tells you he was homeless for a month. What’s the beauty in that?

    Well, life experiences shape who we are as people. Your date probably had to do lots of personal growth and hard work to get back on his feet. That shows lots of character development. We love character development.

    What Should Happen on the Second Date?

    Whatever you want. Seriously.

    People are going to give you some ridiculous rules to follow on the second date, but rules are meant to be broken. There’s no one-size-fits-all for every second date.

    What I will tell you, however, is to look out for red flags. Red flags are things that your date might say and do that might be warning signs to not pursue a relationship with them.

    Here are some huge red flags that should make you run:

    They overshare. Do you ever have strangers full-on share their life story and traumatic events with you right off the bat? That should not happen on the second date. It might be a manipulation tactic for you to feel bad for them. You don’t want to be manipulated.

    They talk about their ex. It’s okay to mention your ex when it’s appropriate, but when your date recalls stories and keeps mentioning them, it’s a little weird. You could be a rebound relationship, which is not something you want.

    They ramble on. Have you ever been on a date where your date just won’t shut up? Yeah, it could be nerves, but if you’re on a second or third date and they’re still doing this, they could be conversational narcissists. It’s not cool to take over the conversation.

    You are the ultimate judge of character. Listen to your gut feeling, and if you get the urge to not ask for a third date, don’t go on one!

    Conclusion: These Second Date Questions Will Work

    You might be nervous. I get it! The dating game can be rough.

    These second date questions will hopefully ease your nerves and give you lots to talk about when you’re getting to know someone new. Plus, your date’s answers to these second date questions will give you lots of data for you to tell if you two have chemistry.

    The best advice I can give you is to breathe, push your shoulders back and get in there! You’re a grade A hottie, and you should act like it.

    Peace out!


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