How to form a deep connection through meaningful conversation
The second date can be a bit tricky. You probably covered a lot of ground- conversation wise-during the first date. The second date is an opportunity to dig a bit deeper. At the same time, you want to continue to build on the chemistry from the first date, you want things to be fun. With these 33 second date questions, you will form a closer bond, you will also find out a hell of a lot more about the guy in question.
I have divided the 33 questions into seven thematic areas. This way, you will get a good grasp of which areas to cover on your next date. (Or ten next dates ;))
It’s also important to understand why these questions create attraction. By understanding the why, you will have an easy time coming up with your own unique questions, tailored to your situation and the things that are important to you.
Conversation makes the world spin
When you talk about something important to you, that subject evokes strong feelings within you.
For example, you will feel happy if you talk about your favorite activity. Those feelings are easy to transfer to the person you are talking with. We associate those feelings with the other person and, as a result, feel warmer toward that person.
That’s one part of why conversation is such a fantastic tool to spark romance.
Talking about dark subjects
We also all have a deep longing to be seen for the unique person we are.
So, when you talk about traumatic events, you feel closer to the other person because you share profound truths about yourself.
If the person continues to react positively towards you, you feel accepted.
Thus, mixing lighthearted conversation about your passions with more serious subjects is important. Keep this in mind when you consider which questions to ask on your second date.
Do share who you are
If you leave the date and don’t feel infatuated with your date, one of the reasons can be that you didn’t truly share who you are. We must allow them to see us to feel close to someone. You might have held up a shield, and the conversation might have been too lighthearted.
Be vulnerable
You have to make sure that you are vulnerable and open since those very acts are a way to develop feelings for another human. We feel connected with the other person when we share intimate information.
Allow yourself to share things with your date that is a bit scary to talk about.
If you want to become better at this, read our article How to appear vulnerable to a man.
Don’t be too negative
I know, life can seriously suck. So, when we share about those serious subjects, we all tend to complain. This might be Ok with your friends since they know you very well. But being too negative is like suffocating that fire of attraction. Few people find negativity attractive.
Do talk about your struggles but focus on how those very struggles made you a better person.
1. Ask about passions
As mentioned above, the best way to get someone to like you is to have him talk about his passions.
He will naturally transfer a bit of all that passion onto you. When we feel passion in the presence of someone, we also feel passionate toward them.
Ask him exactly why he is so passionate about this special subject.
“Asking about the “why” is a neat trick to make the conversation flow.”
The more you can make him think about his passion in new ways, the more impressed he will be with you.
Find common passions
One of the best ways to create attraction is to find a couple of things both of you are deeply passionate about.
The more specific your shared passion, the more sparks will fly. If you are both crazy about a particular genre of music, you will atomically have lots of fun talking about the subject. To find such gems of commonality should be one of your goals with your second date questions.
Similarities make us connect
Another reason this technique is so effective is that we, as humans, like people similar to us. We like to discover that someone shares our political views or is also a big nerd when it comes to cooking. We feel validated in our existence if we discover common ground.
Examples of questions
What makes you excited right now?
What’s one of your biggest passions?
What is one thing you were interested in as a kid and are still interested in today?
What’s your favorite thing to do?
What helps you relax after a stressful day?
What would your perfect day look like?
2. Ask about happiness
By asking someone how they view happiness, you actually learn a lot about their values and moral standpoints.
Happiness is the key to the human experience. It’s also sometimes contradictory to other things we want to achieve, and that makes it an interesting subject. How do you measure happiness?
Happiness will tell you the truth about another person.
You might not want to come in guns blazing and try to nail down if the man in question lives up to your high moral standards, but by finding out his stand on happiness, you will get all the information you need.
Happiness versus progress
You can also ask how he views happiness when it clashes with other values. Exactly how important is happiness to him? Is it the most important thing, or are there other things that have more meaning for him?
Examples of questions
What does happiness mean to you?
What makes you happy?
How happy are you on a scale?
How could you improve your overall happiness?
3. Ask about his goals
If you ask me, it’s always fun to talk about goals. Thinking about the future and how we want to spend our future brings out the best in us.
Talking about goals is also less charged than many other subjects.
Examples of questions
What goals do you have for the coming year? What plans do you have in your life that you are yet to achieve?
What would you create if you could create anything?
What countries do you want to visit in the coming year?
When you want to challenge him a bit, ask why he thinks he hasn’t achieved his specific goals yet. That single question will tell you a lot about your date.
4. Ask about success
Talking about success can be surprisingly funny.
Especially if you dig a little bit deeper, success means different things to different people. Talking about success can lead to a debate, and a debate can be hot. (If done right.)
To create attraction with these kinds of questions, it’s also good if you can create an image of how the two of you can be successful in the future. Everyone wants to be with someone who supports their goals.
Examples of questions
How do you define success?
Have you reached it?
How do you plan to reach it?
Are you as successful as you would want to be? If not, why not?
5. Ask about sex and attraction
It’s a date, alright. There needs to be sexual tension and flirting. At the same time, you don’t want too much information. You also don’t want to think about your date’s history or other options.
But a few questions acknowledging that you are interested in him as a sexual being will help your case, so to speak.
It all depends on the two of you and your comfort level with sex. Talking about sex, done right, can be one of the sexiest things ever.
I will acknowledge that walking down this road can also go horribly wrong, so when you are on your second date, proceed carefully with the questions below.
Examples of questions
What do you find attractive?
What kind of normal day activities do you find surprisingly sensual?
What dish do you think is the sexiest dish? (Say this one playfully and have him come up with a good motivation.)
Do you have any kinks? (Only bring this one up if you are comfortable with the answer.)
What’s your favorite part of having sex? (Same as the above.)
What’s your specialty when it comes to your bedroom skills?
Do you have any secret fantasies you haven’t fulfilled yet?
Bring on the chemistry
My biggest recommendation is to combine asking these questions with being flirty in other ways. There are many ways to show a person that you are sexually attracted to them. For a comprehensive guide, read our article How to flirt with a man.
One way to flirt is exactly what we are talking about here, ask interesting questions and attentively listen to the answer. That’s, in fact, already flirty. To not come across as too serious with all these questions, make sure you are also playful. Check out our article How to tease your crush, for the crash course.
6. Ask about mistakes and growth
Yes, this is a sensitive subject.
But when you give a man the opportunity to be vulnerable in your company, he might actually feel even more attracted to you.
Vulnerability and attraction are closely connected. As humans, our desire for connection is one of our most significant needs. We feel connected to another human when we share who we really are.
When you are aware of the mechanism, you will be able to talk about failures in a way that increases attraction. Check out our article How to get a man to be vulnerable, for even more tips and tricks.
Don’t be judgmental when you want to create attraction. Whatever he says, be more accepting than he was expecting, and he will like you as a result.
Ask about shortcomings
There is a reason these kinds of questions are so popular when companies are hiring. They force you to reflect on your negative sides. They show the other person how self-aware you are.
You can tell a lot about a person by how they handle obstacles. Or what they perceive to be their personal obstacles. That’s why these kinds of questions make excellent second date questions. They are a bit tough.
Examples of questions
If you could change something in your past, what and how would you change it?
What is one thing you would want to change about yourself?
What is one of your shortcomings you are working towards trying to change?
Thread carefully
A note of caution, those questions often don’t increase attraction. Make sure your tread lightly and doesn’t come across as critical. You want to come across as deep, not as an asshole.
Only go there if the atmosphere is already flirty and lighthearted. Be playful and friendly. You don’t want to roast him.
7. Ask about impact
We all go through life having different experiences, but what makes us the unique person we are is all about how those experiences affected us.
Your second date is an excellent opportunity to ask questions about what shaped him into the human he is today. These kinds of conversations often span from being fun and easygoing to being deep and serious. Thus, they are perfect for creating attraction.
Examples of questions
What book impacted you the most?
What album had the biggest influence on you?
What movie is your all-time favorite?
What moment in your life changed the direction of your life?
Arrive well prepared
There is nothing wrong with planning questions for your second date. In fact, being well prepared shows that you care about the other person and are eager to get to know him.
Do use the question I have suggested above, but also prepare a couple of questions on your own. Tailor those questions to who he is and what you are interested in finding out.
Write down your questions
You can write a list of questions on your phone. When you are on the date, check the questions. You can do this discreetly, or you can even tell him that you are checking your questions. Do it in a playful way, and he will be impressed with your level of investment.
A Final Note
The second date comes with a bit of pressure. The stakes are higher since you have already established a mutual interest by the very fact that you are on a second date. The right questions can help you create attraction and add a lot of depth to your budding romance. Good luck and enjoy.
Moa Ailert is the founder and editor-in-chief of Her Brilliant Friend.
She has a bachelor’s degree in philosophy and plenty of insight into human psychology from traveling and living in different places around the world.
Moa is currently based in Portugal where she has a guesthouse; Villa dos Irmaos.
She has various websites, among others Ericeira Insider, but Her brilliant friend is her true passion project.
