This year has been a challenging one for all of us and has caused us to navigate new waters. When it comes to dating, there is no exception. I’ve had plenty of friends ask me “When is it okay to go and meet someone considering COVID-19 is still around?” or “Is it disrespectful to ask someone to come over for the first date because of COVID-19?” I’m obviously no dating or relationship expert, so I talked to Orlando’s Sole Male Dating and Relationship Coach Zach Chandler and asked him some questions.
As we get used to our “new normal” how do we navigate the dating scene when COVID-19 is still active in the United States?
With respect to those who have lost their lives due to COVID-19 or those who believe this is an over-exaggerated media pandemic, we are nonetheless in different times, regardless of how you see it. The world is evolving, and hopefully so are you. As you grow older and your ideals, beliefs and desires change. Therefore, you must learn to adapt. Too often, we forget that we outgrow ourselves.
With that in mind, connecting to another person can seem challenging now, as the typical things we hoped to do are possibly unavailable or cause reason for concern. Before I met my wife, we spent 18 months long distance and by default were forced to find ways to truly build a strong interpersonal connection where there weren’t the distractions of intimacy, splitting time with friends or family, or questioning who you are with.
Navigating this remote / virtual space feels different but I encourage those stepping into the dating world to reevaluate and restructure what your former version of safety looks like and to allow yourself to be creative.
There are a multitude of different ways you can connect with someone over video. A few ideas I’ve suggested to clients I worked with were:
1) Simultaneously ordering your favorite food for each other and then eating at the same time while sharing your thoughts on the meal chosen for each other.
2) Traveling the world virtually through Google maps viewing different locations, setting your zoom background to a unique place and guessing where it is, or touring virtual museums around the world together at the same time.
3) Learning a new hobby together. (For example, playing guitar)
4) Watching a TV show at the same time and then talking about it afterwards over video.
There are so many new innovative ways that you can be creative in dating so that the first date isn’t so awkward.
Let’s say you have an at-risk family member at home, is it rude to ask someone you’re going on a date with whether or not they’ve been safe prior to the date?
We are in uncharted territory with this pandemic and we are having to ask a lot of uncomfortable questions of each other. Asking someone how safe they have been has the potential to push someone away. I guess I am of the belief that if you have turn someone off or push them away simply by asking what their social practices have been because you are trying to protect someone at home then that is certainly someone that doesn’t have your best interests in mind moving forward.
Think about yourself, if this were a loved one close to you and your closest friend wanted to get together and you asked them the same exact question, I am going to assume their response would be very forthcoming and honest. I would also assume they would be understanding of the reason for your concern.
It may hurt if you have done this but I certainly think there’s an eloquent way to ask someone what their social practices have been simply by informing them that you do have someone who is of high risk and it is your responsibility to make sure that you have their best interest at heart.
What would you suggest would be an acceptable, yet safe, first date?
A few things I suggest to clients that I work with regarding first dates… First off, sitting across from a table of someone can feel very intimidating. Understand that not everybody likes coffee, and some people don’t like the pressure of drinks, and certainly don’t use dinner for a first date.
The reason dinner dates can go terribly wrong or send the wrong message is because it sets a very high expectation moving forward of what dates will look like, especially depending on the location. Additionally, imagine starting a date and within 15 minutes realizing that you are not interested and you can’t wait for the bill to come. However, the appetizers haven’t even shown up yet, and now you’re in for the long haul. Cue the fake phone call from your girlfriend that something happened at home and you must go.
Keep it simple. Play to your creative side. Showcase something new and different. This is a perfect time to do that. It’s actually a really great time to find something in the community to do where you can even be socially distant. Orlando has a lot of beautiful places to offer. I’m a big believer in side-by-side interaction and being outdoors and doing things such as walking, hiking, checking out a new neighborhood or participating in nature walks.
Having spent 16 years in social services and working with very challenging clients, I’ve learned that some of the best ways to connect with someone is to be in a space where you’re not sitting directly across from someone and where your body language is equally non-threatening.
Body positioning on dates is really important! Furthermore, outdoor activities lends itself to that perfectly. Just be creative, there’s nothing sexy about coffee/drinks on a first date. Of course the dynamic of your connection with this person can certainly lend itself in feeling like a cup of Joe could be appropriate. However, if that’s the case, grab a cup-to-go and walk somewhere together.
How do you measure your compatibility with someone if your dates have only been Digital so far? (i.e. FaceTime calls) Are there any factors the person should look for when deciding whether or not to move the relationship offline?
Too often, people can mistake compatibility with attraction. We tend to see the best things in the wrong person and the worst things in the right person. There’s no rule that you both have to like the same thing or that opposites actually do attract. I encourage those who are dating to not get hung up on preferences and dealbreakers and let the energy flow. Date outside of your comfort zone. It can be easy to get caught up in physical attraction or finding out that you like some of the same things. At the end of the day you may not end up liking the same music or binging the same shows on Netflix, as tastes change.
It is extremely important, however, to pay attention to whatever your relationship goals are. If someone aligns with your relationship goals, everything else will fall into place no matter how similar or different you are.
When it comes to taking that next step in this new virtual reality, the only time that it’s the right time to move a relationship offline is when it feels right mutually, in time. It is in the very same fashion that you can mutually agree that a relationship is becoming exclusive, it has to be something you are both mutually interested in pursuing. Unfortunately, with these wild times, we’ve added a new level to dating which is starting virtually and moving into that reality.
Some singles are more experienced with this transition, as migrating off of dating apps can be a very similar process and procedure. For others, especially the non/tech generation, it can be fairly new and overwhelming. Take your time, trust yourself, and be sure to openly communicate with the person you are interested in.
Is it acceptable to ask someone you haven’t previously been out with to take a COVID-19 test prior seeing them?
I’m a little on the fence about asking someone to take a screening test for COVID-19, but here is my answer to this dilemma. First of all, it can make someone feel really uncomfortable to ask them to take any sort of test before moving into any new phase of a relationship.
The easiest way to tackle this if you’re very concerned is to say something like “I never thought in a million years that this would be a step in the dating process but I am going to go and take a test myself to ensure that I am safe and not impacting you or any of your loved ones before we go out. Is that something you’re willing to do as well?”
Asking in this fashion shows someone that you’re not just asking for them to take a test, but that you’re looking out for their best interests by first taking a test yourself. However, understand that this just may not be something someone is willing to do as they may have been practicing safe social distancing already.
Additionally, understand that there are limited tests and that this person may feel strongly that this is a poor use of COVID-19 tests. You can possibly avoid ever having this conversation by simply asking how they feel about testing, with respect to their special distancing practices in relation to the COVID-19 incubation timeline.
You may find out by asking that the person you’re interested in feels strongly that you both should. You may also find out by asking that your partner feels that tests are truly meant for those who are at risk or impacted and that you can both find a creative way to see each other that doesn’t put ourselves at risk, even if it means reinitiating better social distancing habits.
What are key questions to ask someone that you're interested in?
When having those first dates online I encourage asking more open-ended questions (questions that do not result in a simple yes or no), and that you do your own homework and look up some creative questions.
A few recommendations to ask and don’t ask are:
- Do ask – “So what are you passionate about?” I have worked with clients where this was the only question they needed to ask on a date because it helped to organically flow into every other question throughout the entire date. This should be your first question.
- Do ask – “What do you love about your job?” Instead of trapping someone into asking what they do for a living which may turn into this negative cycle of why they hate their job, instead ask what they love about their job. This will allow them to stay in a positive space about what they do for a living. Naturally, someone will share exactly what they do, but this allows the conversation to be brief because you’re just asking what they love about their job. This way, you cut out the mumbo jumbo part of the conversation where you may not entirely understand what they do for a living anyway, which is okay.
- Do ask – “What is a perfect Saturday or Sunday for you?”
This is a much more light-hearted way of asking ‘What do you do for fun?”. This will allow someone to share what types of things they would like to do in a much more imaginary space. After asking these questions, everything else should come naturally. If you have shared things over video, I encourage you to write some of these down so you remember to touch on them during the date. There’s nothing worse than repeating yourself on a date for something that you probably should have remembered. For example, if someone shared that they recently hiked Machu Picchu, and it was something really special to them, find a way to bring that into the conversation to show that you remembered.
- Don’t ask – “So what are you? (nationality)” This is a really insulting way to ask someone about their nationality.
- Don’t ask – “Why are you single?” This is like a really bad interview question that can make someone really uncomfortable having to answer. There’s often a much longer answer that will come over time that is probably none of your business.
- Don’t ask – “What do you do for fun?” There is a much more creative way you can ask this question. Remember…Passion!
- Don’t ask – “What do you do for work?” This question can lead you into a space where all you do is talk about work. Again…Passion!
- Don’t ask- “What is it that you’re looking for?” To me, this seems like a pretty easy answer that most people overlook. You’re looking to see if there’s mutual interest and that’s why you’re on a date together, right? To ask, ‘What is it that you’re looking for?’ is to suggest ‘What do you want out of this?’, and that’s just not the type of messaging you want to convey to the other person. It’s not natural so don’t ask it.
Is there anything else that you would like to add?
The truth is, these are new days. Everything we are forced to do now looks different. Nothing about this pandemic is funny but there is a way that you can delicately address all these issues by using a tasteful bit of humor to avoid some awkwardness during the process. It is a great time to be creative with dates, be dynamic with questions, convey empathy towards others and show that you are being sensitive during this time and throughout this process.
As the sole Dating and Relationship Coach in Orlando, my goal is to work with clients to tackle these types of issues, even given the new and changing times of this pandemic. There are a lot of things that become barriers to dating and relationships. Typically these are internal barriers that are often reflected externally. Yet, sometimes these barriers can also be external entities, such as this pandemic, which changes the whole dating paradigm. It’s a really great time to look inward and work on yourself. Use this time to improve on your interpersonal and communication skills and recognize your dating habits both good and bad.
Meet Zach Chandler

Zach Chandler is changing the dating and relationship game by offering a unique and personalized coaching service that focuses on self-care and internal development helping clients build the self-confidence to find love or improve their romantic relationships. Often, the biggest disconnect in dating and relationships can often be the inability to recognize the gap between what you think people see, and what people actually see. Closing this gap starts with self-awareness and accountability and allows people to see what you actually want someone to see.
Zach’s mission as a Dating and Relationship Coach is to work with clients on these internal and external challenges and ultimately closing this gap by building confidence through techniques and one on one coaching. Zach will help you ‘Get Your Heart In the Game’.
If you’re looking for more dating coaching and tips, you can listen to Zach’s Podcast “The Catchmaker” or you can connect with Zach directly on Instagram, TikTok, Twitter, and Facebook.