Three First Date Questions to Jump Start Conversation

You did it! They agreed to the first date. Butterflies are doing aerial gymnastics in your guts, scenes from any romcom you’ve seen in the last 10 years are playing in your head, and maybe you’re asking yourself “what the heck am I going to SAY?”

I’ll offer a couple of conversation starters, and - spoiler alert - you don’t have to just use them on first dates. Let’s give you a pep talk and think about the setting of these big moments!

The pep talk

Here’s the pep talk: it’s so easy to fall into nail biting anxiety about first dates, to the point that by the time you’re walking out the door you may want to turn around and hide out with Netflix for another night.

Shout out to my favorite gay girl influencer, @hi.poppylaur, but remember that all that nervousness is also excitement! Think about all the reasons you said yes to this experience: what are you most excited to know? What sparks do you want to grow? 

Anxiety tends to make us overfocus on ourselves, crowding out the other people we’re trying to connect with. Hold that anxiety gently - a lot of us have a lot riding on these romantic connections - and also try to refocus on the other person. The first date is threshold - full of mystery, drama, surprise, and adventure. It is also an experience you create together, so choose questions that draw you both in (and get them to talk more, worry less about what you say).

the dinner party

“Who are 5 people you’d invite to a dinner party, living or dead? And why?”

I love this question because it opens up a lot of possibilities for the answer. They can answer with silliness (Jack Black and Monk?), tenderness (beloved grandma and their college professor?), or clues about their life (first partner and their celebrity idol?).

How they respond can also help you gauge where they are emotionally - do they want to keep it light, or are they ready to share more vulnerably? You can then match their energy when you share your answer.

The info dump

“If you were awarded an honorary Ph. D. in a topic, what would it be? Tell me about it.”

If you read my essay on friendship in Lord of the Rings, you probably can guess my answer. As much (or as little) as we try to cultivate cool personas, basically everyone has a niche topic they can’t wait to nerd out about with a willing audience.

This question allows the answerer to open up without being too raw or vulnerable, and to feel like they’re on familiar ground. Use your active listening skills, ask real clarifying questions, and follow any rabbit holes that pop up - you might just end up in Wonderland.

the story

“What’s your favorite life story to tell? Let’s hear it!”

Similar to the infodump question, it allows the person to open up at their chosen level of vulnerability and speak on familiar ground. This question also usually gets you a little closer to them, there can be insights into their character, past experiences, and important figures in their life. 

It’s worth it even if it doesn’t “go anywhere”

Dating can feel like a slog, and that magic can be hard to feel sometimes, but remember that a conversation, a meal, an outing with a new person is worthwhile in and of itself. You aren’t a failure, and the experience is not a failure, if it doesn’t result in true love.

During the 2014 polar vortex, I got mocktails with a girl I met on OKCupid, then we practiced hula hooping in my apartment at 3am before platonically falling asleep. Ten years later, she and I share birthday greetings and infodumps about COVID harm reduction on facebook. Definitely worth the $14 for lime juice and gingerale and some awkward non-sensual gyrating.

Focus on being excited, being present, and being inquisitive, and you’ll leave the date feeling better no matter if romance blooms or not.

Folks at an actual Skip the Small Talk event