My #1 online-dating pet peeve is bad conversational skills. It doesn’t exactly bode well to begin an exchange with someone you presumably hope to impress by merely saying “Hi.” Sure, maybe that works in a bar setting, where a person can get an immediate, at-a-glance sense of your vibe/style, but a Tinder inbox requires more from you than that. To be interesting, you have to be interested.
That said, we’re at a strange moment in history (to say the least) where “What’s up?” or “How’s it going?” can come across as oblivious or even insensitive. (How the fuck do you think I’m doing, Chad??) But you also don’t want to veer too far into commiseration land, because the trials and tribulations of quarantining are not exactly fun, fresh, flirty conversation fodder. So what’s a modern dater to do?
I’ve come up with 50 questions you can ask someone on your dating site/app of choice that have nothing to do with the pandemic situation. Sure, it might come up in some people’s answers, but only if they want to go there. Asking fun questions in your opening message is always a good idea, but particularly so at a time like this when everyone wants a dose of escapism and connection – that’s probably why they’re looking at their dating-app inbox in the first place. Try some of these and let me know how it goes!
- What’s the best piece of advice anyone ever gave you about [romance/business/creativity]?
- What song or album are you obsessing over right now?
- What’s your favorite memory from childhood?
- What’s your go-to comfort food?
- When you were a kid, what did you want to be when you grew up, and how does that relate to what you do now?
- Who is the most famous person you have met?
- What’s an outfit you feel amazing in and why?
- What’s the best thing you know how to cook or bake, and how did you learn to make it?
- What’s a movie you wouldn’t necessarily say is your all-time favorite, but that you love nonetheless?
- What’s a weird inside joke you have with a friend and how did it start?
- What’s a common misconception about your job?
- What was the last book you read, and did you enjoy it?
- Do you feel like you’ve found your “life purpose” yet?
- What country would you like to move to if you had the chance?
- When was the last time you did something that made you nervous?
- Did you have any weird hobbies when you were a kid?
- What’s your morning routine?
- What’s your favorite holiday?
- What is the wildest lie you’ve ever told?
- What’s your favorite scent?
- Who would you consider a hero of yours and why?
- What do you keep on your nightstand?
- Are you an introvert or an extrovert?
- What part of your body do you like the most?
- Who was your favorite teacher in school and why?
- What would you do with your time if capitalism was abolished?
- What’s your favorite word?
- What role does social media play in your life, and how do you feel about that?
- What’s your favorite thing about your home?
- What celebrity do you think would make a really great roommate?
- Which fictional character do you most identify with and why?
- What’s a piece of media that can reliably make you cry?
- What’s a task most people don’t like doing that you actually enjoy?
- What do you think will be the biggest technological innovation in our lifetimes?
- If you were famous, what would you want to be famous for?
- What’s an item of clothing you wish you owned?
- What makes your best friend so terrific?
- What’s the last problem you solved?
- What’s one of your hidden talents?
- What’s the most athletic thing you’ve ever done?
- What’s a social rule or expectation you totally ignore?
- What’s the most common compliment you receive?
- What’s the best kiss you’ve ever had?
- If you were going to start a podcast, what would it be about?
- What’s an out-of-character decision you’ve made recently?
- What’s the best Halloween costume you’ve ever worn?
- What’s something you love, without really knowing why you love it so much?
- What’s a bad habit you’re trying to break?
- What’s the fanciest event you’ve ever been to, and what did you wear?
- What question do you wish more people would ask you?