First dates run the game—they can be exciting, exhausting, mysterious, boring, easy, or laborious. What determines the success or disappointment of a first date has less to do with an immediate spark and more to do with creating the right conditions for turning that spark into a lingering flame that leaves us burning to experience more. When we’re just beginning to connect with a new person, it’s all about context, education, seduction, and connection. When dating is tough, it can feel like a game that we don’t know how to play. But by focusing on these four areas, we can revel in un-gamified playfulness—that quality of romance, humor, and ease that, when combined with an authentic connection, inspires both parties to go deeper.
Context is Key
Going to the same noisy bar for every first date with every new person is a sure way to experience the dreaded first date fatigue that so many singles have become accustomed to in modern dating. Dinner and drinks are great, but playing tennis or a board game can show us how they win and lose (which tells a lot about a person). Asking them to help us pick out a gift for somebody can center an entire date around thoughtfulness and generosity. But if you really want to get to know somebody, invite them and their friends to a party with your friends.
In this context, we get to observe how our date engages with both friends they know well and strangers they’ve never met before. We get to hear about how their friends view them and they get to learn how our friends view us. (And we all know that our friends often have a kinder view of us than we have of ourselves—plus they are happy to share it.) Our friends also have our best interests at heart. They might see our date with more clarity than we do (and we’re going to talk to them about it all anyway).
If we don’t have a connection with our date, there’s always the possibility that we’ll connect with one of their friends and/or that they’ll connect with one of ours, or that two friends might form a connection. The worst case scenario is that nobody gets along well, in which case, it’s infinitely more pleasant to experience that situation surrounded by friends than all on our own.
Some Dating Advice? Think of it as an Education, Not an Interview
We all like to think that we come into a first date with an open mind rather than a checklist, but deep down, most of us know it’s a bit of both. For those of us who have been through marriage and divorce, in and out of many long term relationships, or have gone on more dates than we can count, holding tight to our checklist and prepared topics can feel like a necessary safety net to avoid wasting time. We seek to maximize the efficiency of our dates, to get through them so we can skip right to the cost-benefit analysis. But our hyperfocus on being productive can cause us to miss the rich tapestry of what makes a person unique, compelling, or even a surprisingly good match. Just because someone doesn’t check all of our boxes, doesn’t mean they don’t have something to offer that we’ve never thought of before. Answer the following questions honestly:
When you go on a first date, do you tend to talk more or listen more?
Do you ever find yourself listing off your resume?
What topics do you tend to focus on during a first date? Why?
What topics do you tend to avoid? Why?
Learning about a new person is also a process of allowing them to learn about us. This mutual education is an intimate and vulnerable act with a stranger that can be intimidating in both directions. We could all benefit from addressing that dynamic more explicitly on first dates. Try asking your date:
What is your favorite topic to be asked about on a first date?
What questions would you like to ask me but are too afraid to ask?
What is something about you that surprises people when they find out?
What is your least favorite part of dating?
What do you hope for when you go on dates?
How do you think this one is going so far?
To Seduce and To Be Seduced
When a date is going very, very well, the intense physical and emotional fusion we experience is possible because we don’t know each other yet. Desire needs mystery and, in the beginning, everything is mysterious. There is so much depth to be discovered. And that process of discovery can be intoxicating. In the early stages, merging and surrendering feel relatively safe because the fundamental separateness between two new people creates infinite space to play. Seduction is a way to explore the boundaries of each others’ worlds, histories, fantasies, and desires—and that type of play is an education unto itself. If the attraction is there, and if it feels appropriate, try asking:
What is your idea of a perfect romantic evening?
What is an aspect of sexuality that feels mysterious to you?
Where is the strangest place you’ve had sex?
What non-sexual thing feels sexual to you?
Connection or No Connection, Follow Up
Enjoyed the first date? Say so. It is so nice to receive a message or call that confirms mutual interest and a desire to see each other again. That one small, simple gesture can make a person’s whole day. The moment we find out that the person who made such a positive impression on us feels similarly about us, we become flooded with endorphins and excited to flirt, play, and see each other again.
Didn’t enjoy the first date? Say so. You don’t need to find an excuse or supply an explanation. “I very much enjoyed meeting you. That said, I didn’t feel a connection between us so I don’t know that we will meet again. I think you’re a wonderful person and I wish you all the best.” Ultimately, there is nothing you can say that makes rejecting someone or being rejected any easier, but you can communicate in a way that doesn’t make the other person feel devalued or dismissed. And if we find ourselves on the receiving end of one a message like this, it’s okay. If we are willing to keep putting ourselves out there, there will always be more people to learn about who want to learn about us.