Skip to content

24 Essential Second Date Questions & Topics

Congratulations! The first date was a success, and you enjoyed getting to know each other.

Now that you know it has the potential to turn into something more serious than casual dating, you need to show up prepared for this second date.

Think about what you’d like to know about your potential partner that will deepen the connection without making them feel like they are being interrogated.

What to talk about on a second date, you may wonder?

If you’re still struggling to find good topics to touch upon, here are some important second-date questions to ask.

What made you want to go on a second date?

Good for you for landing that second date! Time to hit them with this loaded question of what made your date decide to hang out with you again.

It could be that they felt a strong connection right off the bat and wanted to explore something a bit deeper. On the other hand, maybe they just had a really fun date and couldn’t think of a better way to spend their free time.

It is a good question to ask on a second date because it helps you figure out what you are doing right and what they like enough about you to make them want to spend more time with you.

It will also come in super handy for future dates and for laying a foundation for a healthy long-term relationship.

The confidence boost from the affirmations and compliments also doesn’t hurt.

What is the funniest first date you’ve been on?

Talking about exes and past love interests is always tricky, especially when a relationship is new. However, when approached tactfully, it can provide a lot of insight.

This question is a great example of how to explore your date’s romantic past without seeming too nosy and putting too much pressure on them.

In addition to learning a bit about your date, sharing funny and disastrous dating stories is a really good way to break the ice and ease up the tension. You may find yourself laughing the night away with your back-and-forth story-telling.

It also helps to figure out what not to do on subsequent dates so you don’t end up on their list of disastrous dates.

Do you remember mentioning [insert topic here] last time we went out?

If you want to avoid awkward silences but feel a bit shy opening up, you can always refer to something interesting they said on your first date. That will put your love interest in the spotlight and make them share some extra details and continue the conversation.

Where do you see yourself five years from now?

By drawing attention to their goals and aspirations, you’ll find out what makes them tick. Are they motivated to do better and grow, or are they doing just fine in their comfort zone? 

It is one of the basic second date questions that will let you discover if you are going in the same direction, sharing the same values, or absolutely no common denominators.

What do you think we have in common?

By drawing a parallel between you two, your date will reveal a lot about how they see you as a person and what they value about themselves and the world in general. It’s one of those questions for a second date that will tell you whether you understand each other right off the bat.

Do you see yourself as a religious person?

Religious beliefs and personal values play a huge role in determining how the relationship will work out. Whether or not you consider yourself a religious person, it is important to establish where your partner or date stands on the topic early on. Things will be much easier in your relationship if both of you are on the same page.

On the other hand, if your beliefs and value differ, there is still hope for the relationship. You just have to be ready to make some adjustments and compromises for everyone’s comfort. However, it is important to know when to call it quits as extremely differing views will be the end of your relationship.

What are some dating rules that are important to you?

Everyone has their own dating playbook with rules. It could be anything from the levels of intimacy they are comfortable with to how fast or slow they like to play things.

Perhaps your date believes in always being asked out and not doing any of the askings. Or you could be on a date with someone who subscribes to the 90-day waiting rule for intimacy.

Finding out these rules early on is crucial as it helps you manage your expectations accordingly. You will also get to learn what your partner expects from the relationship. If your needs and what you are willing to give match up, things will likely work out well.

What do you value most in a relationship?

It’s very important to know if you two are compatible as partners, so feel free to ask about what they need and want in a relationship. If you have already established that you like each other, this is a great second-date conversation. Again, it’s crucial to be on the same page if you want to give your relationship a chance.

What would be a relationship deal-breaker for you?

For any relationship to work, there has to be flexibility and willingness to compromise from both parties. However, there are always topics that give you the right to put your foot down on.

These deal-breakers could be anything from relationship values like fidelity to pet peeves like tardiness and poor hygiene.

Make sure you understand what your date considers to be a major, uncompromisable deal-breaker.

This is a good question to ask on a second date because it helps you to get some insight into their expectations from their partners and thus establish whether or not you are a great match for each other.

Why did your last relationship end?

Asking about why your date’s last relationship ended could give you a lot of information. It all lies in how they react to the question and what their answers are.

Your date’s response and reaction will clue you in whether or not your date has moved on from their previous relationship. If they are angry or otherwise very emotional, they may still be in the process of dealing with that breakup. On the other hand, if they are open to answering and calm about it, the chances are that they have fully moved on.

The specific answer to why the relationship ended will tell you what to expect from your date should you two end up together, whether or not they were at fault.

What are you most grateful for in your life?

It is a must when it comes to second-date conversation topics. It’s a window to their past where you can take a peek into your potential partner’s most treasured moments. If they feel like sharing, you’ll probably find out things that gave their life a new direction and shaped them into the person they are today.

What is your happiest memory?

After all the heavy hitter questions you lay on the table, it will be nice to pump up the mood with a trip down memory lane.

Let your date share some memories of happy times, whether it was a childhood birthday or last week when they got to catch up with a long-lost friend.

You could also throw some of your own stories into the mix for a nice back and forth.

In addition to lifting the mood of the whole date, these happy memories will be a fantastic way to learn what makes your date tick and how to make them happy.

What’s your most embarrassing memory?

Sharing embarrassing memories is another way to make sure that your date ends up in giggles and wheezes. However, it isn’t necessarily all about the giggles and good times.

Sharing embarrassing and cringey memories is a sign of vulnerability. If your date is ready to open up about these moments in their lives, it means that they are very comfortable around you and trust you enough to share the unflattering parts of their past.

Just make sure to share some of your own so that your date doesn’t end up feeling exposed under the hot spotlight.

When was the last time you cried?

Another way to establish whether or not your date is comfortable being vulnerable with you is if they are willing to share the last time they cried. Whether a man or woman, talking about these low moments that drove them to tears is very impactful.

Beware of a date that answers with something like “I actually don’t cry” or “crying is for the weak.” This shows a serious lack of emotional awareness and a tendency towards unhealthy coping mechanisms like repression and denial. Chances are they have had a few good cry spells but don’t feel comfortable expressing such vulnerability to other people.   

Is there something you regret not doing?

Life gets busy; things take their course. There’s always something to distract us from what we know we’d like to do or experience. This question will probably help you find out more about your date’s past and establish some common ground.

What is one activity or subject that makes you lose track of time?

There are few things in the world of dating as attractive as a person sharing their passions and interests. Whether it is to do with their line of work or a random hobby that they got hooked on, it is always nice to hear someone speak about something that they can completely and effortlessly get lost in.

These passions and interests are also a sign of a well-rounded individual. It shows that your date has taken the time and effort to work on themselves and find something that makes them happy and fulfilled. They are also unlikely to be unhealthily codependent.

What is the scariest experience that has happened to you?

We all have something that scares the ever-living crap out of us. From things like heights and spiders to the fear of failure or loss, this vulnerability is what makes us human. What makes all the difference is how we choose to approach those dreadful experiences.

By asking your date about what their scariest experiences are, you can get an idea of how they approach challenges, as well as their willingness to buck up in the face of danger.

If the experience included them overcoming irrational fears, it is also a good indicator of someone willing to step out of their comfort zone and learn.

How have your previous online dating experiences been?

These days, most people have had at least one experience with online dating. Even that one lonely evening when you signed up and chatted up a few matches right before quitting counts.

You could make your second date a bit more interesting by sharing some of these online dating experiences.

It is best to stick to the embarrassing ones, the total fails, and proper online dating horror stories. These are usually very relatable and a lot more fun to share than past success stories.

So don’t go too deep into sharing about how you met the one who got away online. It will just make the date awkward. 

Ask more about what you already know

If you are not sure what to talk about on a second date, you can always go back to something you’ve already talked about the first time you met.

There are probably interesting things they already shared that you’d like to know more about. So feel free to ask for more details. It will let them know you are interested in them and paying attention to what they are sharing.

What is the best present you’ve ever received?

Gift-giving is a huge part of making a relationship work and could be a major love language either for you or your date.

It is a very easy question to segue into if you feel the conversation is struggling a bit. For example, you could ease into it if you notice a birthday happening in the restaurant. You could also pop it into the conversation if your date is about to go on a holiday.

Furthermore, understanding what they consider a good gift will come in handy if your dates lead to a serious relationship. That way you know what to get them for the big events and holidays.

Who Is Their Favorite Family Member?

You have probably talked about your families on the first date, but now it’s time to take it further. Ask them about who’s their favorite family member, who they look up to, and why. 

It will give you a better perspective of their family tree and how they communicate, establishing a great base to build your relationship upon. It’s one of those second-date topics we all should cover.

What is the scariest/bravest thing you’ve ever done?

That is a good second date question because it shows how determined your future partner is to leave their comfort zone and expose themselves to the unknown. You will see his willingness to face their fears and learn new things.

Do you enjoy your work?

For most people, work is a huge part of who they are. It affects everything from our schedules to our day-to-day mood.

Understanding whether they love their job and what they like about it will also let you in on their secret passions and goals. It is another way you can figure out whether or not you are perfect for each other.

It is also important to appreciate the fact that job fulfillment (or unfulfillment) often spills over to relationships as well.

So, if your date hates their job or is constantly frustrated, prepare yourself for instances of that stress seeping into your relationship.

How do you like to spend your weekends?

Asking how your date typically spends their weekend is important for three main reasons:

The first is that it sheds more light on their interests and what they feel most comfortable doing. For some, a perfect weekend is spent outdoors, whether partying, running errands, or going on adventures. For others, it is a time to relax at home and catch up with their favorite shows.

The second thing this question does is help you learn how your date socializes. Chances are, this is what future weekends together will look like.

Finally, asking how your date spends their weekends could give you an opening to invite them to spend one with you, landing you a next date!

Wrapping It Up

These are some of the basic dating for dummies second date questions to ask a guy or a girl that will help you smoothly transition onto your third date and ultimately onto the next, more serious, phase of your relationship.

There is no need to rush; take your time and allow yourself to feel comfortable in their company.

At one point you’ll notice signs she wants a serious relationship with you.

Get Free Dating Advice!

Signup now and receive an email once I publish new content.

I understand that my email address will be used to receive free dating advice newsletters from ( Privacy Policy )

I will never give away, trade or sell your email address. You can unsubscribe at any time.