Let’s be honest, first dates can be intimidating. You worry about what to talk about, whether conversation will flow naturally, if small talk will rule out or, worst of all, if there will be dreadful moments of silence. For those of us not blessed with the gift of gab, meeting someone new can be downright scary. But don’t let those feelings of anxiety or nervousness get in the way of making a great connection with a potential love interest. Take into consideration these 10 questions to initiate thoughtful conversation the next time you go on a date.

1. What does a typical day look like for you?
This question is important for a few reasons. It is a natural way to introduce the person’s career (unless they are retired) and give them the opportunity to talk about it in a natural way. It sounds much less abrasive than “What do you do for a living?” If you truly want to get to know your date and see if your lifestyles will match, you need to know what their day-to-day life really looks like. Fitting in with someone’s routine is important when you start looking for love and deciding what’s important in a partner.

2. Tell me about your family. Do you have kids, grandkids, pets? (Yes, pets are considered family!)
Asking about your date’s family is important. If they are parents or grandparents, you can be pretty sure that they are proud ones, and love bragging about their families. Watch their face light up as they talk about their kids and see how excited they are when they show you pictures of their grandchild at soccer practice. You can learn a lot about someone by the way they talk about their family and the type of relationships they have with them.

3. What was the best vacation you have ever been on, and why?
We love this question because it allows you to see how compatible you are with your date in terms of traveling. Surprisingly, traveling and how you travel can be a deal breaker. Some people love traveling, while others find comfort in staying close to home. There is no right or wrong way, but being on the same page in terms of traveling is crucial for a relationship to succeed. This question also allows you and your date the opportunity to see if you have traveled to any of the same places. Was your experience in that location similar? Did you see similar sights? Did you experience the culture the same way? Traveling can be extremely romantic and is a great way to bond with your partner. If you have a love for travel, maybe one day you can explore the world together!

4. How was your day?
Sounds simple, right? But this simple question can bear a lot of weight. Simply taking the time to ask how someone’s day was and truly listening and responding to them can move mountains in terms of relationships. A lot of times, as you get older, your priorities change and what you look for in a partner differs. Communication and friendship are important; having a partner that listens and truly cares how your day is, every day, is ideal.

5. What is your biggest passion in life?
This question is a character question. You can get to know a lot about a person based on their biggest passion—the thing that gets them out of bed every morning and pushes them to be better and do better. Plus, having a passion in life means they are motivated by something each day and gives insight into their personal values. Who doesn’t love a passionate person?

6. What is on your bucket list?
You and your date can go back and forth about your personal bucket lists and discuss why certain things are on that list and how you plan on checking them off. (Maybe you can check some off together on dates in the future!) You can get to know more about your date’s adventurous side, their personal or professional goals, etc. all based on this fun question.

7. Who is the most inspirational person you have ever met?
Most likely, when someone answers this question it will be followed with a story or an explanation that digs into why that particular person is or was so inspirational. A lot of times the person your date cites will have helped shape them into the person they are today, and that is always something fascinating and intimate to know about someone else.

8. What are you most proud of?
In the end, we all seek chemistry, and when we finally let someone in, the sense of intimacy from a quality, sincere question can help us discern a clearer path to true romance. Use authentic conversation as a building block to the intimacy you desire.

9. What is your perfect Saturday?
If you want some insight as to what you can plan for date No. 2, ask this question! Not only will it help you see if your lifestyles fit together, it will give you some ideas for future dates and adventures you can explore together.

10. What is the most important component of a relationship? What is it you desire most?
You are clearly on a date because you are looking for a relationship, a partnership and someone who you are compatible with; therefore, it’s OK to ask your date what they value most in a relationship. Getting to know what you each desire is important. It goes hand in hand with your personal love language. You may not speak the same love language, but that doesn’t mean you aren’t compatible. It is all about open and honest communication. Once you know what the other person is searching for and desires in the relationship, you can decipher if that is something you too desire and are capable of producing.

Cheers! Now that you have 10 solid questions to ask on a first date to help conversation flow nicely, it is time to get out there and start dating. A bit more advice here: remember to hold eye contact, look directly in the eye and smile when you are talking to your date. Kindness to all makes love the potential, not the problem. Don’t be afraid to be romantic and complimentary, it is the best form of flattery. 

If you are looking for a professional matchmaking service in Naples or Sarasota, MyTopMatchmaker is here to help! We can help guide you through the first phases of dating to make the process simple and enjoyable. 

Mimi Lee, Professional Matchmaker
Locally owned and operated:
3131 S Tamiami Trail, Suite 206
Sarasota, FL, 34239
www.mytopmatchmaker.com

To book a free and fun consultation, call or email: (941) 773-9527, [email protected]