You are taking precautionary measures, practicing social distancing and have taken your conversations from the apps onto the virtual dating platform. Hurray! First dates can be awkward and now that they have moved to video chats, it can be hard to read the room and understand if you’re hitting it off. Have a first date via video? Here are the best and worst questions to ask. 


  • What makes you laugh? We love this question because it helps you understand their sense of humor.
  • What does a typical day look for you? This is a more creative way of asking them what they do for a living without entering the interview style territory tone. Presumably they will tell you they start off going to work which will lead into a more organic conversation about where they work, educational background, and hobbies.
  • What were you like as a kid? Asking about family dynamics on a first date can be a touchy subject for some people, especially if they’re not very close to their family. This question dances around that awkwardness and allows them to tell you stories about themselves and/or their family on their own.
  • Which fictional character do you relate to the most? You could also make it fun and ask if they could pick an actor to play them in a movie, who would it be and what would the movie be called.
  • What sort of vacations do you like to take? Instead of asking when was your last trip and they tell you the place they went to, ask a more in depth question that gives you insight on what they enjoy doing during their time off. Do they tend to like more relaxed on the beach get aways, exploring cities and restaurants, or are they more adventurous and delight in trekking parks and magnificent landscapes.


  • You Seem Great, So Why Are You Still Single? Maybe it seems flattering on the surface, but the tone of this question is that there must be something wrong with them if they are seemingly great but single.
  • Why Did Your Last Relationship End? First date questions should really avoid asking about past relationships. It’s really not your business at this stage. This is a topic that you can cover as you get to know each other more.
  • Interview like questions [How much they make, what are your weaknesses/strengths, work style]: When we’re meeting people for the first time, it can tend to feel like an interview – and each question/answer determines if you will continue to a second date. Unless you intend to collaborate on a work project together, avoid asking interview style questions on your first date. Also, asking someone how much they make is just plain rude.
  • Questions about sex or how many people they have slept with: Any time you bring up sex in the first date, it can come off as if that is the only thing you’re interested in. Sex is an important factor in every relationship but it’s simply too soon to be bringing it up or discussing in length.
  • Do you want kids? We completely understand not wanting to waste your time with someone whose long term goals are not aligned with yours. So often, we get ahead of ourselves when we are meeting people for the first time and start to envision our lives with them (he said he wants to stay in the city but I want to move to the suburbs in a few years and raise a family – this could never work!). Our advice is to relax, this is just a first date. The point of a first date is getting to date number two and determining as you get to know each other if you are compatible.

Bonus Question:

If you’re feeling stumped or maybe the conversation has gone a little stale, a great way to ease into relatively fun banter is by asking something like “I’ve been bingeing (and who hasn’t)  _____ and love it. Have you seen it and/or I’m looking for my next binge fest, what do you suggest?


We encourage you to prepare for your virtual date as if you would be meeting in person. Check out our guide to video dates to help set the mood and push you to take it more seriously. Have fun and stay safe!