While video chat has given us a way to continue dating without interruption, it’s no surprise that most of us are itching to get off the screen and onto an IRL first date. Let’s say that after several months of chatting with the same person, you’re vibing pretty hard. While it’s always a good idea to video chat before you meet up in person these days, you’ll want to find out more than just how fast their Wi-Fi is or how well you click. 

It’s easy to get swept up in the romance of a new connection and forget to gather precious intel. You know his fave video game and you know she’s bingeing “The Office” for the second time this quarantine, but do you know how many people are in their quarantine pod? Do you know their love language? You may have to dig a little deeper to get what’s underneath the surface; that can take time and confidence. 

One thing recent events have taught me is that time is so fuckin’ precious. No one wants to waste theirs on someone who comes with several deal breakers, especially when many people are being way more choosy about who they spend time with in the real world. But nothing is a waste of time if you learn about yourself in the process, says a pillow at TJ Maxx. Bullshit. This isn’t a college elective, this is real life and the clock is ticking. As a 100-year-old woman in single years, I can attest that it’s important to ask the right questions upfront to avoid not just wasting each other’s time, but also to avoid hurting each other’s feelings.

1. Do you wear a mask? 

Look, masks are the bucket hats of 2020. Some people are committed and others don’t even understand the purpose. Make sure you’re on the same page, wherever you stand, before you meet up — in public, mind you.

2. What’s the best advice anyone has ever given you? 

Ask this question and hopefully, you’ll get some good advice in return. And, if the advice came from their local or city health authority? Marry them.

3. What is your biggest pet peeve in a partner? 

If theirs is eating in bed and you wake up covered in cereal crumbs on the regular, you may have some thinking to do. What would it take for you to give up snacking in your lair? 

4. Do you make your bed in the morning? 

This is just a polite way to ask if someone is a total slob IMO. This question will tell you everything you need to know about a person. 

5. What are you a snob about? 

If they answer “nothing” then call them a liar and end the call. Everyone is a snob about something, whether it’s music, coffee, wine, or art. This question gives you an opportunity to size them up and establish some witty banter in the process. 

6. What could you spend the whole day talking about? 

If you could be potentially sitting on the receiving end of some really absurd stuff, it’s best you find out sooner rather than later. Get a sense of their interests, what they geek out about, and what you may have to put up with in conversation at the same time. It’s a win/win/win. 

7. If you could ask me anything what would it be? 

Invite your date to pose a personal question that they may be too shy to ask you on their own. This gives you a chance to get vulnerable — and you don’t even have to put on shoes to find out how they do under pressure.  

8. When was the last time you were in a relationship? 

It’s important to find out what you’re working with; this is an opportunity to see if your date is, say, fresh out of a relationship or a total commitment-phobe. It also opens the door to talking about exes. No one ever wants to bring it up, but we all want the dirt — so go get it! 

9. What did you do this weekend? 

You’ll have a good sense of what your future Saturdays and Sundays could possibly look like after you ask this question. Are they running marathons? Getting too fucked up to remember the weekend? See what happens when they’re left to their own devices.

10. Can I hug/kiss/touch you?

Establish each other’s boundaries before you meet up to avoid any unnecessary awkwardness. Find out if your match prefers a socially distant date or is comfortable with getting a little physical as long as you’re both following the appropriate health and safety guidelines. 

11. How is someone as great as you still single?

You know that they know the answer to this question, but it just may not be the answer they give you. If there’s silence, let it speak volumes and if you know they’re lying, think about why that is.

12. Who have you seen in the last two weeks? 

Last, but certainly not least: Who have you been with!? It sounds like a pretty aggressive question, but unfortunately, times have changed. You have a right to know what your match has been exposed to before you meet up in person. 

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