Everyone tells you to just “be yourself”. I agree, but I’m telling you to be the best version of yourself. There is a way to do this and I will help you bring out the best version of yourself on the first date. But while you’re reading, consider this: what are the differences between these two questions:

What are your interests?
What do you think?

The differences between these two questions and your understanding of them will dictate the shape and direction of your conversations during the first date, and as you follow along, you will understand the nuances and differences between questions such as these.

We talked about how to plan the first date the last time we talked about romance, this time I’m going to coach you about the conversational direction you should be taking when on the first date.


It’s fair to say that most professionals in their 20s and 30s have similar or similar-ish hobbies. They may include: trying out new restaurants, traveling to different places, staying and keeping fit, going out with friends, and progressing their career. And while all these topics differ and vary from person to person, these topics are generally more like a laundry list of “things that I like to do” and not “this is who I am”. The types of conversations that tell you more about a person are the types that reveal who they are, not so much what they like to do. The purpose of the first date is to get to know more about her and for her to know more about you! Catch my drift?

Remember, we’re trying to understand the way she thinks, the way she reacts, and how she views certain situations. This is what really matters, not that she enjoys eating her salads with kale and not spinach or that she prefers the elliptical to the treadmill. The conversation that arises shouldn’t be you telling her all the places you’ve traveled, all your interesting hobbies, which region has the best wine, or your affinity for craft beer. This is not to say that these things aren’t important, they are, but these types of conversations only skim the surface. We need to know more about how she thinks and how she reacts to certain situations and circumstances; these types of conversation allow you to know more about her and whether you want to pursue the relationship further.

Here are some examples of behavioral and situational based questioning that you need to implement when on the first date:

1) “The other day, a friend of mine asked me to be his groomsman, however, I don’t think I’m that close to him. What do you think I should do?”

2) “An old acquaintance from university called me out for drinks the other night, however, the guy never bought any rounds! I’m okay with buying rounds, but isn’t it normal for these things to be reciprocated? What do you think?”

Although these questions may not be entirely applicable to all people, there is however, a lot to extract from the responses. The questions above allow your date to express her opinions as she reveals her thought processes. By directing the topics to behavioral/situational based conversation, you are actually

– Making the conversation a lot more open-ended, allowing for a diverse range of opinions and answers.
– Learning about who she is as a decision maker and her priorities.
– Determining how compatible you are in a subtle manner.
– Indirectly humbling yourself when asking her for advice.


“Be yourself,” I completely agree; but be the best version! By training yourself to ask the questions that really matter, you set yourself up for engaging, open-ended conversations that not only allow you to know about her and her interests but also who she is as a person. Put yourself in the position to succeed and you’ll come away with a date that encourages mutual respect and adoration, and what a way to start a relationship!


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