Lisa Concepcion Blog

Lisa Concepcion Blog

Best Questions To Ask On A Date and Why

lisa concepcion lovequest marketing


As a Love Strategist, I help people find, give and keep love starting with love of self. That said, one of the most loving things one can do for themselves is value their own 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 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. The reason to ask this question so early in the game is because don’t want to have any part of a rebound relationship. You don’t want to be a person someone is using to get over someone or worse; to project feelings for someone else onto. 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 was 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 themselves 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, 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.

Lisa Concepcion is the founder of LoveQuest Marketing, a personal development firm that applies principles of marketing and Law of Attraction to help people find, give and keep love starting with love of self. Lisa shares the valuable lessons she learns on her own LoveQuest journey and believes everyone is always on a LoveQuest regardless of whether they are single or in a relationship. Based in Miami, Lisa offers group workshops, one-on-one sessions and writes, vlogs and speaks on the topic of dating, relationships and self-love. Connect with Lisa via  and via twitter @lisatakesmiami  and her YouTube channel. 

Please follow and like us:

Related posts:


  • JW| April 3, 2016 at 11:35 amReply

    Great post, LIsa. I want to add to this. For some guys, 3 months isn’t even long enough. I’ve been with guys who years later are still venting about the ex-wife. (Oy!) And, yes, it’s a reason to run, run, run.

    • Lisa| April 3, 2016 at 9:15 pmReply

      YES! Agree… a lot of people; men and women get some sort of payoff by carrying past resentments with them. Major red flag. Huge lesson I learned. When I get any whiff of a man seeking a pity party I remove him from a dating prospect and make him a LoveQuest client. Not easy to do since most people prefer to stay stuck because they don’t want to do the work necessary (and it’s ongoing). What they don’t understand is that the more we beat the drum of what is unwanted the more that thing is brought to us. It is Law!! Instead, I tell clients focus on what’s wanted and the emotions associated with it. That’s how you start attracting better people, situations, things into ones life.

      But yeah, I learned some major lessons and now in relationships I strive to inspire never fix and… I come first always. How I feel matters first and most.

Leave comments

Your email address will not be published.*

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>

CommentLuv badge

Back to top
Facebook IconYouTube IconTwitter IconVisit Our Instagram