As a Dating and Relationship Coach, I help people find, give and keep love starting with love of self and one of the most self-loving things is valuing your time. You can never get time back. This is why when dating, it is important that one uses time effectively. You must know who you are, where you are in life, and where you are going so you are able to date with purpose. Without clarity you’re wasting your time and the other person’s time, not to mention money on food and drinks. Here are some of the best questions to ask on a date and why.

1. What do you like most about the work you do? 

Asking people what they do can be off putting. This is a more positive interesting spin on the same question. Plus if after they are asked this question they launch into complaining about their job, you know you have someone who isn’t happy about where they are professionally. If they openly say what they do and what they like most then that is someone who is positive!! It’s a far better conversation starter, which leads to…

2. What do you like to do for fun?

This is very telling of how they spend their free time and who they are. If they say they enjoy going out with friends you could follow up asking where they like to go and how often do they get to enjoy time out on the town. Pay attention to the language and tone you use as not to come across judgmental. Their response is a great indicator of how much they party and where their priorities are. If they say they like to work out and enjoy a hobby then you can launch into a positive conversation about things you like to do and things you can possibly to together. It’s always good to learn that someone has a busy life but not so busy that you question if they have time for a relationship. Which leads to…

3. When was your last relationship?

Ideally this is a question asked before a date is even planned. This is why I’m a fan of the pre-date phone screener. You don’t want anyone using you to get over their ex or worse; to falsely project the feelings they have for their ex onto you. If they say anything less than 3 months they most likely have not done the work to properly grieve and get past the prior relationship. Pay close attention to how they speak about their ex and, how often. If their ex is a constant topic, that’s a huge red flag that they aren’t over them and have no business dating you or anyone for that matter. RUN!

4. If I were having lunch with your most recent ex, your mother and your best friend what advice would they give me about you?

This is a far more interesting way to ask someone to describe him or herself to you. It’s a disarming question that makes a person really think. If they say that their ex would tell you to run because they are stubborn rigid or a total player, that’s very telling. If their mom says that they need a lot of care and attention and no one can be as good to them as they are; you clearly have a momma’s boy on your hands. If the best friend says the world revolves around them then you have a good amount of information. Really listen to how people describe themselves through other people who know them.

5. Love or money?

The correct answer here is both. Successful people don’t live an “either/or” existence. They have a mentality of abundance and that is the kind of thinking someone with self-love has. They want it all. They want all the love, all the money, and all the freedom so they can share it and have an abundant joyous life. If you want to know if a person is an abundance thinker ask them a question that forces them to choose between two things. The abundant thinker will figure out a way to have both. It’s also a fantastic way to launch into a broader discussion about money and their attitude about money which is something you want to size up fast.

6. Did you play sports as a kid?

This is a great way to ease into learning if they have kids or want them. As soon as the word kid comes up, a parent will launch into talking about their kid. If someone wants kids they’ll probably say that they look forward to when they can watch their kids play sports. Wherever you are on the topic of parenting get clear and get answers fast. Don’t experiment thinking maybe their kid is different. If kids aren’t your thing, be truthful from the get go. Conversely if you have kids or want kids be upfront and clear on that too. Best to have these discussions as soon as possible. This is your life. People who love themselves value their time. They won’t invest time in a superficial relationship only to learn a year later that their partner doesn’t want kids or wants them.

Remember it’s not what you are asking; it’s how you are asking. Open-ended questions that draw people in safely usually inspires them to open up. Smile, nod in agreement and soak up the data. Trust your gut and then make your informed decision from there. 

About the writer:

Lisa Concepcion, writer, speaker, vlogger and Founder of LoveQuest Coaching™ is a Professional Life Coach specializing in dating, relationships and self-love. Originally from New York now based in Miami, Lisa candidly shares the valuable lessons she learns on her own LoveQuest journey offering online workbooks and video workshops, group workshops, one-on-one sessions, and seminars, to help people attract, give and keep love starting with love of self. Connect with Lisa via her YouTube Channel or by visiting


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