9 Questions To Ask On a Second Date

I think it’s safe to say that many of us are feeling a bit burned out and overwhelmed while navigating the dating pool today. In 2023, sex and relationships have become one of the most talked about topics of the year, and with no surprise. Not to mention the increasing amount of celebrity divorces we have all come to witness. So, while common talking points should be a no-brainer, today, it could be time to think outside of the box.

Many moons ago when people were dating things just weren’t this complicated. You’d meet someone, express interest, go on a date or two, chat about things happening at the date and if you were lucky, you’d be locked down within 3-weeks. Well, it’s different now, especially with situationships at an all-time high and women still finding themselves pregnant and alone in droves.

With that being said, congratulations you’ve made it to date number two! If you’ve been taking my advice thus far then you’re on this second date having not slept with your potential suitor and perhaps have only kissed him on the cheek at the end of your first date. However, if you met on a dating app and went for coffee, and now you’re going out to dinner or somewhere he planned, then consider this your first date, not a second.

Now that all of that is out of the way, let's dive in. 

WHAT DO YOU ENJOY DOING IN YOUR FREE TIME?

This question is crucial, especially if you’re the type of girl who likes to spend non-sex time with their boyfriend. If your partner is into activities that you simply cannot wrap your head around, you need to know this up front. From here you can decide if you want to shift your perspective and maybe join him on some of his ventures. Nobody likes a boring or pouty girlfriend. Your boyfriend is not going to want to spend his free time with you if you’re huffing and puffing or making him spend unnecessary money. Try to find a middle ground.

WHAT ARE YOUR LONG-TERM GOALS OR ASPIRATIONS?

Asking this question can help you to gauge just how much of an emotional investment you should be making. For example, if you want to be married in the next 3 years, be sure that he has marriage on his bucket list and is actively pursuing a career or job that will assist him in making a livable wage to afford a wife and children. On the other hand, if you’re more of a nomad, be sure that he is, too. He should have no problem picking up and relocating on the fly if that’s what you’re into. Overall, ask this question to get a better understanding of how you should proceed.

WHAT'S YOUR FAVORITE TRAVEL DESTINATION, AND WHY?

It’s important to date someone who is well-traveled or aims to be. The reason is that you want a man who is ready to settle down if that’s what you’re looking for. He is not still wondering about what the world has to offer because he’s seen much of it on his own and now, wishes to venture with a companion. Also, this is a good way to learn what kinds of food he likes and hobbies. Traveling opens the mind and teaches us things we cannot learn in school.

WHAT'S THE MOST MEMORABLE BOOK YOU'VE READ RECENTLY?

If you’re dating a man who has no interest in reading, then it’s probably not going to end well. Men who read are more likely to be better communicators and have more patience. Both of these are needed to build a strong foundation and start a healthy relationship. Plus, you can get an idea of what he’s into—if he likes reading horror books or books on how to unalive someone, then that will be your cue to exit immediately. But, if he’s into more practical things this can give you both something more to discuss.

WHAT ARE YOUR FAMILY DYNAMICS LIKE?

I cannot stress this enough, the type of relationship a man has with his family is paramount. Men who are estranged from their parents or siblings can be a red flag. If you’re a woman who wants a traditional home life then you must seek a partner who has a good support system. If and when you both decide to have children, you will need support. Sometimes life can throw us curveballs which can lead to anger issues, arguments, and resentment. A good family structure can help to alleviate some of the unpleasantries that stress on an individual can bring.

WHAT'S A LIFE LESSON YOU'VE LEARNED RECENTLY?

I love this question because this can be something he learned from a past relationship, a parent, mentor, or sibling, either way, it’s a great question. You want to be sure that this person is open to growing and isn’t stubborn or believes he’s perfect and needs no readjusting. Men who think they know it all or never concede during disagreements are dangerous; winning means more to them than having you in their life. Life lessons can come at any age and you want to make sure he’s still a student of life before anything else.

DO YOU HAVE ANY HOBBIES OR INTERESTS THAT YOU'RE PASSIONATE ABOUT?

This is a good question to ask as you look to appeal to his interests. Depending on the type of man he is, you may be able to learn a thing or two from him. For example, I am not too versed in the world of art, but I dated someone who was and to be honest it was a wonderful experience. His passion for art led me down the rabbit hole and I learned so much. Take it from me, take this moment to learn as much as you can because it could positively change your life.

WHAT'S YOUR COMMUNICATION STYLE WHEN IT COMES TO RESOLVING CONFLICTS?

With this question, you have to be careful. It’s not uncommon for someone to downright lie. There are numerous communication styles: aggressive communication, passive, manipulative, assertive, and more. When asking this question, be sure to ask after you’ve asked a few of the aforementioned questions, because it will give you an idea of how he typically shares communication. If he’s growing impatient, losing eye contact, or appears bored or bothered, then don’t bother to waste your time any further.

WHAT ARE YOUR THOUGHTS ON THE FUTURE OF OUR RELATIONSHIP?

Okay, so maybe you’re thinking it could be too soon to ask this, but the truth is, it’s not. If you want a relationship then this is the perfect time to lay it on the table. This does not mean you want one with him, after all, you’re both still getting to know one another. But you have to set the tone for where things are going so that he knows if he continues to date you, your expectation is to one day get into a relationship.

If he flinches or digresses from the topic, take it as a sign that he’s likely not looking for anything serious. Don’t get me wrong, some men will respond with something you want to hear, such as, “I’m looking for my wife” or “I’m looking for something serious”. The only way to test this is to hold off on giving up the goods for at least 3-months. See how much non-sex time he’s willing to commit.

There you have it, nine questions to ask on your second date. Don’t worry if you stop hearing from him after this date, it’s his loss and he’s probably looking for something casual anyway. Keep your options open, your standards high and your legs closed!

by Danielle Wright