Many things can go wrong with first dates. They can be difficult, exciting, frustrating, confusing, boring, simple, laborious, and even tedious. The success or failure of a first date is less about the spark that ignited it and more about creating the conditions that allow that spark to grow into a lasting flame that inspires us to continue to explore the world. It can feel challenging to be in a relationship. These four areas can focus on unramified playfulness, that quality of romance, humor and ease that, when combined with a genuine connection, inspires both partners to go deeper.

Context is key

It is easy to fall into the trap of going to the same bar every time you go on a first date with a new person. While dinner and drinks are lovely, playing tennis or other board games can reveal a lot about the person. A date can be centered around generosity and thoughtfulness by asking them to help pick a gift. If you want to get to know someone, host a party with your friends.

This context allows us to see how our date interacts with friends and strangers. We hear from our friends how they view us and learn how we view them. We all know that friends tend to have a more positive view of us than our own. Plus, they are happy to share it. Friends also care about our best interests. Our friends might be able to see our date more clearly than we do. We’ll talk to them anyway.

There’s always the chance we will connect with one another’s friends, and they’ll link to one of our friends. Or that two friends might ally. Worst case scenario, nobody gets along. In that case, it is infinitely better to be surrounded by friends than alone.

A little bit of dating advice? It’s not an interview but an education.

Although we all prefer to believe that our first date is with an open mind and not a checklist, many of us know that it is a combination of both. It can feel like an unnecessary safety net for those who have experienced marriage and divorce, been in and out of many long-term relationships, or want to be safe. Our goal is to maximize our time and quickly get to the benefit analysis. However, our obsession with being productive can lead us to overlook the rich tapestry that makes someone unique, compelling or even a good match. Even if someone doesn’t meet all our criteria, that doesn’t mean they cannot offer something we haven’t thought of. These questions are honest:

• Do you talk more on your first date?
• Are you guilty of listing your resume?
• What are your favorite topics to discuss on a first date? Why?
• Which topics are you most likely to avoid? Why?

It’s also about learning about someone new and allowing them to know about you. Mutual education is a vulnerable and intimate act with a stranger. It can be intimidating for both of you. Let’s not forget that first dates are when we need to address that dynamic. Ask your date:

• What’s your favorite topic for a first date?
• Which questions do you want to ask but are afraid to ask?
• Is there something you are most surprised by that people discover about you?
• Which is your most minor favorite aspect of dating?
• What are you hoping for on your dates?
• What do you think about this one?

To seduce and to be drawn.

If a date goes very well, intense physical and emotional fusion is possible since we don’t yet know each other. Desire requires mystery, and everything starts as mysterious. There is so much to discover. It can be a fascinating process. Merging and surrendering can feel relatively safe in the beginning stages because of the inherent separation between the two people. There is infinite room to play. Seduction allows you to explore the boundaries between your worlds, histories, fantasies and desires.

• How do you envision a romantic evening?
• What aspect of sexuality feels most mysterious to you?
• What is the most bizarre place you have ever had sex in?
• What other non-sexual thing do you feel sexy about?