Got A Zoom First Date? Here Are The Best Questions To Ask According To A Matchmaker

Virtual date on FaceTime

Got A Zoom First Date? Here Are The Best Questions To Ask

10 Best Questions To Ask On A First Virtual Date According To A Matchmaker

So, you’ve showered, swapped your sweatpants for something more polished, and poured a glass of wine (or two) — alas, you’re all geared up for your first Zoom date, and you’re feeling equally anxious and excited. Now, the only question is, WTF will you talk about? Any first date can feel a bit nerve-wracking, but if you’re not used to virtual hangouts, a video date might feel even more daunting. The key to keeping a natural flow is asking the right things, and luckily for you, I’ am matchmaker and I’ve rounded up the best questions to ask on a virtual first date.


In an ideal world, your first date conversation is effortless — but even if you’re super compatible with someone, you may need a little help getting the ball rolling. Asking certain questions can be a lifesaver in this regard because they allow you to maintain momentum in your convo while learning insightful tidbits about each other. Remember: These questions shouldn’t feel like an interrogation — you’re trying to get to know them, not grill them, after all.


Certainly, having some foolproof questions in your back pocket can come in handy whenever there’s a lull in conversation. That said, ditch the old go-tos (like “where are you from?”, or “what do you do?”) and try these questions instead to break the tension, take the lead, and best of all, test your connection with your virtual boo.

  1. What were you doing right before we met up?
    This is a great one to start with because it doesn’t feel forced. Were they working on a new project for their job? Were they trying a new virtual workout? Were they cheffing up a gourmet lunch? Asking what your date was doing before you started your video sesh will provide some valuable insight into how they spend their time. Plus, it can easily inspire follow-up questions and offer an opportunity to share what you were up to.
  2. If this date weren’t virtual, where would you want to go?
    I love this question, because it can offer a glimpse into what your Zoom partner’s ideal date looks like. Knowing whether they would have chosen to check out a trendy new speakeasy downtown, go indoor rock climbing, or visit a new museum exhibit may shed some light on both their personality and interests. After comparing notes on where you might have gone if you weren’t confined to virtual dates, you can fantasize about the things you’d like to do together once quarantine is over.
  3. What are you missing most right now?
    Talking about the coronavirus outbreak on a first Zoom or FaceTime date is tricky territory. You don’t need to pretend like it doesn’t exist, especially since it’s obviously impacting your dating life in a major way, but you also don’t want to dwell too much on doom and gloom. This question strikes a nice balance because it acknowledges that you’re both in a tough situation without forcing your date to talk about their feelings on the pandemic. Notice how open your date is in sharing their emotions, and listen intently to what it is they’re missing — because that can tell you a lot about what’s important to them.
  4. Where’s the last place you traveled to?
    According to research by Expedia, travel is hands down the most popular topic for first-date conversation(even beating work!) — and that’s not really any surprise. Talking about exciting destinations you’ve been to unlocks endless possibilities for discussion. You might discover you’ve both been to the same locations and can compare experiences, or that you have the same cities on your travel bucket list. Not only that, but traveling is a passion that apparently makes you more attractive. In fact, an eHarmony study of more than 100,000 profiles found that travel is among the top interests most likely to get users’ attention and inspire communication requests. So go ahead and brag about your last amazing trip — and while you’re at it, ask about your date’s, too.
  5. Are you more a go-with-the-flow kind of person, or a planner?
    This is one of those get-to-know-you questions that can help you to figure out how compatible you are. Not only that, but it can be helpful to know going forward. If your date is a planner, they may be more open to scheduling Zoom dates a week in advance, but if they’re not, they may be more likely to spontaneously hop on a video chat next time they’re free and thinking about you.
  6. Would you say you’re an introvert or an extrovert?
    Again, this question can provide some valuable info into your date’s personality. It can be tough to get an accurate read on a first date because everyone feels the pressure to “perform” and put their best foot forward. You may be surprised to discover that while your date seems extroverted, they’re actually an introvert at heart. Talking about how your date sees themselves (and how you see yourself) can also offer some helpful hints on the nature of their social life, and how they like to spend their free time.
  7. Coffee or tea?
    This-or-that questions (like Instagram or Twitter, cat person or dog person, spring or fall) are a fun way to break the ice while also weighing your differences. I like this one because even though it’s a lighthearted topic, people tend to feel surprisingly passionately about it. Plus, knowing how your date caffeinates in the morning may prove helpful down the road (*wink*).
  8. Learn anything interesting this week?
    Lots of people are using quarantine as an opportunity to take an online class, read some nonfiction, or take up a new hobby. So, why not have a little show and tell to share what you’re both learning about lately? You may even find out you have a common interest or curiosity.
  9. What’s one thing you’re looking forward to right now?
    It’s always a good idea to keep the conversation as upbeat as possible on a first date, especially since the current circumstances are obviously stressful. This question helps to cultivate a sense of gratitude for the good things going on in your lives and helps to maintain a positive tone in the convo. Besides, you may learn something interesting about your date’s day to day life, and what really excites them.
  10. What was the last thing you watched on Netflix?
    Talk about an old standby — this question is more relevant than ever, given that so many people are relying on streaming services to keep them entertained during quarantine. Don’t underestimate the power of asking this one, though, as it can reveal whether or not you and your date have the same taste in movies and television. As an added bonus, if you do happen to like the same kinds of content, you automatically have a potential plan for your second virtual date. Now that’s a win-win!



HOME FOR THE HOLIDAYS, Dylan McDermott, Charles Durning, Robert Downey Jr., Holly Hunter, Cynthia Stevenson, Anne Bancroft, Geraldine Chaplin, 1995, (c) Paramount/courtesy Everett Collection

Are You Dreading Going Home For Thanksgiving Because You’re Still Single?


What Is ‘Stashing’? Everything to Know About This Problematic Dating Trend 

Christmas in Washington Dc

Professional Matchmaker Gives Advice For Singles At The Holidays!