First dates are weird, they’re awkward. You’re sitting alone with someone you barely know, drink in hand, trying to decide if you want to get all up close and naked with them. For me, this is honestly one of the most stressful environments around.
Public speaking? Fine, I own the room, I control what happens. Huge parties? Whatever, if I run out of things to say or start feeling awkward I can just fade into the background and let other people take the lead on the conversation for a bit. But dates? One on one, sitting across from each other at the bar, dates? That’s where shit gets complicated.
Good dates are great! Even bad dates are interesting, but boring dates? The kind where you’re just staring around the restaurant, poking a soggy salad with a fork and trying to come up with something, anything to talk about that isn’t the weather? Ugh, those are the kinds of situations I have nightmares about.
In an attempt to quell my own fear of something like that ever happening, I’ve created a list of questions, stories, and conversation kickstarters that I can use the next time I’m standing awkwardly next to someone cute at a complete loss for words.
When I interview people at my day job one of my favorite questions to ask is always “what are you passionate about?” I love it because it’s the best way I’ve found to break through the nerves, once you get them talking about something they really love you can see their anxieties just melt away as they get caught up in the excitement. I’ve found that people are always the most attractive when they are talking about their passions, their eyes light up, they smile excitedly and wave their hands animatedly, they really come to life. This is also a quick shortcut to identifying the kinds of people who don’t have any passions at all, and those are the kind of people that I personally have a really hard time connecting with.
Conversation Starters: What are you passionate about? || If you could be famous for any one thing, what would it be? || What is your dream job (it doesn’t have to actually be a “real job”)? || What gets you up in the morning? || Do you have a passion project? || If you won the lottery tomorrow, what would you spend the rest of your days doing? || Who are your heroes/idols/role-models? || What are you most proud of?
These are the kind of conversations that feel like fluff, they’re low stress and they make people comfortable, but, when leveraged the right way, can tell you a lot about the kind of person you’re with. Do they make pragmatic decisions, even when their choices don’t really matter, or are they prone to creative flights of fancy? Do they use this as an opportunity to make clever jokes or do they very seriously ponder each and every possibility, in case, one day, the zombies really do come? What’s great about this is that by building a hypothetical world with your new paramour you are putting yourself on the same team as them and engaging the creative centers of the brain, both of which are great for fostering bonding.
Conversation Starters: If you could have a meal with anyone, living or dead, who would it be? || Hey, see that guy over there? What do you think his story is?1 || If you could have any super power, what would it be? || If you were to build your ideal vacation spot, what would it look like? || Alright, here it is, the desert island question. You can only have 5 [objects they’ve expressed interest in]s, which ones do you bring? || What is your zombie apocalypse strategy?
Memories and Storytelling
Storytelling is one of my favorite methods of communication. It lets people talk about their experiences, point out their strengths, display their wit, entertain, and charm. It’s always good to go into a date with a few killer stories up your sleeve- you know the ones, the ones you wind up telling at every party to crowds of enraptured listeners. The ones you’ve told so many times that you’ve polished them down to their purest, their funniest and their most engaging. You don’t want to monopolize the conversation though, make sure your date has the opportunity to share some stories of their own.
Conversation Starters: So, tell me about your worst date EVER. (You can’t say this one, I’ll cry.) || What’s the best vacation you’ve ever been on? || What is the most absurd thing to ever happen to you? || What is the best party you’ve ever been to? || What is the strangest food/activity/thing you’ve ever tried? || Tell me about your most embarrassing moment. || Who was the weirdest/most interesting person you’ve ever met?
We all have weird little stories and facts about us, the things that make us unique, and the things that you start to cherish when you partner with someone. Find out what makes your new person stand out, what makes them weird, and what makes them who they are.
Conversation Starters: What is one thing that everyone seems to love, that you absolutely hate? || What is your guilty pleasure? || What is one of your pet peeves? || What nonessential item could you not live without? || What fictional characters or stories had a huge influence on you? || What bad habit do you wish you could break? || Do you have any irrational fears?
The Heavy Stuff
This is the controversial stuff, the stuff people will tell you that you can’t talk about on first dates, but I don’t entirely agree. Sure, you want to have some social calibration, you don’t want to roll out your deepest darkest secrets before the appetizers arrive. Not because you should be ashamed, but because it shows that you don’t have a very good barometer for what is considered “socially appropriate.” That said, if the conversation moves in a way to get you to a place where you can talk about the things people really care about- politics, religion, sex, and relationship preferences, etc, you have the potential to learn quite a lot about your date mate. If you agree you’re going to find yourselves connecting on a much deeper level than you ever could have over your favorite TV show, and if you disagree, well, better to find that out now.
Most of these topics are hard to just come out and ask about, it can sometimes be easier to just slip mentions of them into conversation and see how the person reacts, rather than interrogating them on their politics in a way that will, almost invariably feel like a test (that may or may not get you honest answers).
What are some of your favorite first date questions and topics?
- Building lighthearted fictional backstories for other people in your vicinity can be a fun way to engage your date, but remember that being spiteful or mean isn’t a good look on anyone. [↩]