1st Date Questions


Every date has a purpose. You get to know your date better and start building a connection. Having fun and laughing together is a great way to connect emotionally. When people connect emotionally, they feel safe. When they feel safe, they are more likely to open up. You have to work at peeling back the layers, especially with a stranger. While keeping in mind that no one wants to feel like he is being interviewed, it is important that you come away with two or three answers to “must-know” questions by the end of each date. How else will you vet your dates effectively? Listen to his words, then, see if his actions match his words. Repeat. The quality of your date cannot only be based on your emotions and feelings; those sway like the wind.


The questions you want answered are based primarily on your goals: what you are looking for in a partner and your vision for your life, your lifestyle. These questions would help you discover the “real” stuff, the stuff beneath the stuff, the stuff that matters. In no particular order here are some questions you might ask:


1.    What would you do if you won the lottery? People who are already living a passionate, fulfilling, and authentic life won’t be doing anything too differently from their present life post lottery. Sure, they may move into a bigger apartment or travel more luxuriously but chances are they are already traveling and enjoying their lives. If the answer is, “I can’t wait to quit my crappy job and leave my crappy apartment and hang out with my buddies, buy a bunch of new cars”…. Well, let’s think about why their current life sucks so much and, more importantly, why they haven’t done anything about it. Ambitious, much?


2.    Tell me about your childhood. Who are you closest to in your family? Yes, what you hear is true. The relationship with your father, if you’re female, and the relationship with your mother, if you’re male, matters. How well you adapt emotionally matters to the health of your future relationship. The most important element for long-term relationship success is one’s emotional fitness. Read that again. Now, I’m not saying if he has a weak relationship with his mom, you should drop him. I have a poor relationship with my dad but I own it. Also, there is no blame. I’m not trying to change the past. I don’t harbor anger or resentment (any more). So it’s not whether his experience was a negative one. Rather it’s to do with how well your date processed those experiences.


3.    What do you like the most about your job? How did you get into this industry? You can uncover his motivation and passion. Some are driven purely by the desire to earn a lot of money. Others are really passionate about the work they do. If you’re lucky, you have both. You’ll find out more about your date’s values.


4.    Tell me about your best friend. What qualities do you like most or admire in him or her? You can learn about the qualities that are important to your date and what he values. Is it loyalty? Shared activities? Are they bound by history?


5.    What is the toughest/hardest thing you’ve ever had to experience? You can learn about how he deals with challenges, how resilient he is and how he deals with stress.


6.    Tell me about your last vacation. You can learn a few important insights here. Does he value down time and recharging or is he a workaholic? Does he like to travel? How adventurous is he? You can also tell a lot about his spending habits. Some people like to travel on a budget even if they are making good money. Others only travel luxuriously. This is a view into his spending habits but more importantly his lifestyle preference.


7.    What is the one thing you have learned about yourself based on your past relationships? Does he blame? Does he take responsibility and ownership? Is he self-aware and open to learning and growing? The only element common amongst all your relationships is you.


8.    What qualities are you looking for in your ideal woman? If he doesn’t know or if his answers are generic, then he hasn’t given it much thought. You can’t get what you don’t know you want. Is he focused on looks and external qualities, like a person’s title, height and address? Is he value driven?


9.    Don’t be afraid to ask if he is interested in marriage and family in the next couple of years. As a dating coach, I find that SO many women are afraid to ask this question for fear of rejection. Listen, wonderful ladies: if your date does not want these things relatively soon (in the next several years), then who cares? You just met. He is not saying he doesn’t want to settle down with YOU. It’s not about you. He barely knows you. Alternatively, you’re not saying you’re just looking for a relationship, that’s easy. You’re looking for a relationship with THE RIGHT guy. Your date may or may not be that guy. Why would you not ask these questions and waste months or years only to find out later that he doesn’t want children, for example? You can’t take this personally. Note, a high majority of heterosexual men will say, “Of course, we want to settle down and have a family.” What you want to find out is if this is on his agenda in the immediate future, not some day.


10.  IF the date is going well and you’re connecting and laughing, then you can playfully ask at the end of the evening, “So, I’m having a great time; what do you think so far?” I would not suggest asking this question if you want to bail and you know it’s a no go or if you’re not sure it’s going well or if you like him but you’re getting very tepid feedback. Proceed accordingly.


The answers are only as good as your questions. If he answers in an interesting or unexpected way, follow-up with more questions. The key is to listen openly. Men and women reveal a lot about themselves on the first date if you pay attention. Don’t be so focused on asking the questions that you miss what he is trying to tell you.


How do you know if you should move him to date number two? Make an assessment based on his questions and your interaction. If you had fun with him, if there was an emotional and physical connection and if you were attracted to him as a person, then it’s a consideration. Listen to your gut. If something feels off, don’t ignore it. Your intuition will steer you in the right direction.


Don’t take your dates so seriously. It is a couple of hours of your life. Above all, be yourself and have fun.  




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