First Date Conversation Tips… that Eliminate Small Talk


3 Online Dating Questions You Must Ask

Your email exchange online dating is much more than your opportunity to find someone to go on a date with ASAP! Unless of course you’re a fan of sitting across from a total stranger who you met briefly online and knowing within moments that this is going to be a wasted date because in no way are you a match.

Instead, online dating is one of the best opportunities to pre-qualify your dates before you commit to that in-person meet-up.

So what do you talk about and what questions should you ask in order to increase your chances of an in-person connection and decrease those “ugh!” instances where you know you’re doomed at first face to face glance? It’s all about digging in, asking strategic questions, and extracting important information about who they are, how they became that person, where they are going in life, and what their dating purpose is.

Sound too time and energy-draining? Yes, you are doing a bit more work on the front end, but it will save you loads of real-life time and energy, plus save you from getting burned out and disappointed by online dating as a whole.

Here’s what to ask and why:

QUESTION 1: What do you do and why?

Why: “What do you do?” may reveal status, true, but that’s not the point because at the end of the day, you’re not living with status, you’re living with him, and by “him” you are living with his career too. Translation- his personality, hours, vacations, date-nights, the way you’re treated, the way he expects to be treated, his bedroom demeanor, how you dress, over-all your daily and long-term life are all dictated by his career. I call it “Career-Typing.” It’s a “type” generalization that reveals much more than their sign, clothing style, car, height, and looks. You are also seeing his work-attitude, his passions, what propelled him to want to go into X career in the first place.

QUESTION 2 : Tell me 5 random things about you…

Why: Unless he takes it as a joke, he will likely think about this one for a second and tell you some pretty interesting and introspective things… revealing things. He may share his education, honors, lifestyle, upbringing, talents, idiosyncrasies, taste, social status, or quirks. It may also reveal things that are on your must-have or won’t-stand list that will immediately turn you off or on. The answers to this question may be the time that you decide to stop responding to him, and move on, OR make you even more intrigued.

Sample (and real) Answer:

“1. No brush or comb necessary as after showering, I can throw some gel in my hair, and voila, its ready to go. 2. I can tie a cherry stem with my tongue 3. I’m a poor singer, but enjoy karaoke so long as it’s a private room 4. I try to have a dark piece of chocolate everyday 5. I like to dance, and really enjoy classes, but still haven’t mastered free form.”

What does his answer say about him?: I too am a poor singer, but will consider it if in a private room (which also says something about his finances). I love that he enjoys dance classes, which shows that he is open to learning new things and doesn’t mind looking silly in front of others. The cherry stem thing says that he has a very flirtatious and sexual side.

QUESTION 3: How have you changed in the last 5 years? Where do you see yourself in the next 5?

Why: This may show if he is introspective, if he learns from mistakes, if he is self-aware, self-critical, if his ego is in check, what he is looking for, and what his experience level is.

Sample (and real) Answer:

“Good question. I’ve grown to place more importance on friends / family, although they’ve certainly always been very important to me. I have evolved in terms of the relationships I have; I’m a bit of a late bloomer in that area, and 5 years ago (maybe a bit longer) I the relationships I had with women were less serious and meaningful than the ones I’ve had in recent years. Over the next 5 years I’d like to start a family (assuming I meet the person I want to start a family with), professionally I’d like to see my business continue to develop (I won’t bore you with the goals), and I’d like to continue to be very close to my family and friends.”

Take Note:

It’s the “and why” or “and how” part of the question is essential. Go beyond the fact and into the reason behind it. You can truly take any mundane topic and find it’s depth if you just do a little digging. Even when it comes to the question “What’s your favorite ice cream?” If you don’t ask “and why?” you will likely get an answer like “French Silk Ice Cream”- which must have a story to it since it’s kind of an obscure favorite, but you didn’t ask “why.” Or worse, the answer could simply be “vanilla”- something so plain and so easily judgable that you might even be inclined to shut them out right then! But what if the “why” is because they are “obsessed with toppings and vanilla is the perfect blank slate”… that’s a pretty interesting and compelling reason to let them stick around.