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My Complete Guide to COVID Dating in Fall/Winter 2020-2021

As we head towards winter and COVID cases (and lockdown restrictions!) have started rearing their ugly head, I've been getting questions from clients, and even friends and acquaintances, about what to do about dating.

Some are seeking advice because they are increasingly uncomfortable dating face-to-face; others because governmental lockdown restrictions are decreasing their access to regular face-to-face date setups.

Some of us, if we’re honest with ourselves, might even be excited about these limitations: mayyyyybe this is our opportunity to give ourselves a break from the apps, right? Right . . . ? (My answer: NO. Take a break if you must, but, as I’ll explain below, now is a better time than ever to work on some of the crucial skill sets you’ll need to date successfully.)

Whatever the reason, nobody seems to know how to date in this brave new post-pandemic world. Especially as the weather gets colder and our access to the outdoors, which during the summer provided at least a relatively-safe way for meeting other singles, starts getting limited, everybody I meet seems to want to know: “What do I do about dating?”

After fielding countless questions and complaints about how frustrating it is to date during a pandemic - that FaceTime dates are boring, how difficult it is to meet people, that it’s impossible to know whether someone else is on the same page regarding COVID restrictions as you, what to even do for cold-weather dates during COVID, that everybody keeps asking to meet in person, that nobody wants to meet in person, that it’s difficult to assess people’s intentions when dating virtually, that nobody seems to want a relationship, and that it’s difficult to meet people organically when our only outing is to the corner market - I decided to write a comprehensive guide that covers all (or pretty much all) of the questions I’ve been asked about pandemic dating, especially cold-weather pandemic dating, in 2020, and into 2021!

So. Without further ado, I present to you: "My Complete Guide to Dating in Fall/Winter 2020-2021."

Let's begin.


My Guide to Pandemic-Friendly Cold Weather Dates:

First of all, I would be remiss if I didn’t mention: I am always going to advocate for social distancing. Because of that, I put these date ideas together with the maximum level of social distancing in mind. That said, I also recognize that everyone has the ability to choose for themselves how they are handling this pandemic. For that reason, each of the date ideas outlined below allow for a range of distancing discretion.

With that out of the way - let's kick things off. To date safely, it's smart and helpful to make your first date a phone call, followed by a FaceTime/Zoom or two. From there, it will be up to your discretion whether you stick to FaceTime (try a FaceTime coffee date, FaceTime drinks, or even a FaceTime dinner or movie!) or move on to one of the additional options outlined below.

1. Walk + Coffee

  • If you bundle up enough, this date can be warm winter day-appropriate, too. Bring or grab a coffee-to-go, walk around town or at a park, and chat.

2. Fall Sunset Picnic

  • My partner and I did this a LOT over the summer. If you live somewhere warm enough to picnic, Fall sunsets are the best, and a picnic can be a great way to still have a traditional-feeling date, even if you aren't comfortable going to a restaurant (or can't). For optimal social distancing, bring separate blankets, and covers/separate serving utensils for the food.

3. Drive-In Movie

  • Drive-in movies are a classic date activity, and most cities that have drive-in movie theatres have kept them open, even during returning COVID restrictions. For a COVID-friendly date, I'd recommend separate cars with open windows, but go with your comfort level, and have fun!


  • Especially during the Fall, hiking is a way to enjoy the newly crisp temperatures and colorful leaves. Obviously, this isn't an first date idea ;) - be safe! But it can be a fun, outdoor way to take an existing connection to the next level.

5. Meet Up In a Location About a Half-Hour Away & Explore Together:

  • My partner and I live in Colorado, so a typical weekend day for us looks like driving to a little mountain town and exploring, always with our masks. You and your date can choose to make this date as distanced as you need it to be - you can get coffee or bring coffee, get take-out or bring a picnic. It's still Fall in many places around the country - take advantage of the leaves before the weather turns cold!

So. With date ideas covered, let's move on to the really juicy stuff - this is the part of the blog post where I convince you that a global pandemic, if you're creative and resourceful, can actually be a GREAT time to date. (Trust me on this - it’s gonna be great.)


Pandemic Dating As an Opportunity

As lockdown restrictions mount, pandemic dating is, increasingly, virtual dating, and while virtual dating comes with its own set of challenges (less spontaneous, more difficult to assess chemistry, fewer opportunities for physical connection), I would like to advocate that it also offers its own set of opportunities. As I wrote in this post, distance in the early stages of dating can actually be a unique opportunity for building improved habits of connection. If approached with an eye for opportunity, pandemic dating can be a space for connection and learning how to adapt to relational obstacles.

For those of you who have DM’d me complaining about the abysmal state of communication in modern dating - you can celebrate! Virtual dating is your chance to take action on everything that you hate about modern dating.

If you want to date in a safe, ethical, responsible way during COVID, you’ll need to master the skill sets of direct communication, boundary-setting, and pacing. I’ll go into each of these skill sets (and variations on them) in detail below, but for now, just know that not only are these three skill sets absolutely essential to dating during a pandemic, but they’re the same skills that you need to be a really effective, responsible dater after COVID, too.

These are skill sets that I work to build with my clients when they come to me for help with COVID dating (and, realistically, dating in general!) and these are the skill sets that I advocate you diving into if you plan to date

into COVID and beyond.

Also, a note for those of you who are feeling like they want to eschew dating entirely during the pandemic: Deciding that you don’t want to date during a pandemic AT ALL NOT EVEN A LITTLE BIT can be a symptom of avoidance of the vulnerability that it takes to learn the skills necessary to be an effective dater.

I’m not saying that you have to date during a pandemic, but if you find yourself secretly heaving a big sigh of relief that you have a reason not to date right now, it may be worth exploring why. Are you burnt out from dating, and do you need a rest? (If so - take a rest! We all need some R&R.) Or do you feel intimidated by dating overall, and are you using the inconvenience that comes with pandemic dating as another reason to put off taking full responsibility for your love life? If it’s the latter . . . well, I have a treat for you. Trust.

Without further ado.


Pandemic Dating As an Opportunity for: Learning Direct Communication

Perhaps virtual dating’s most frustrating limitation is that it’s pretty much impossible to do anything at a distance other than talk. But: this is also what makes virtual dating a fabulous opportunity to practice and build strong communication skills.

On a Zoom call, you have, quite literally, nothing but time. You can ask the tough questions in a relatively risk-free environment. Ask what this person is hoping to get out of dating. Ask about their values. Ask where they see themselves in 5 years. You literally have nothing to lose - if you get an answer that you can’t live with, I meannn . . . the odds of you seeing this person IRL anytime soon are very slim, and the end of the date is a mere push of a button away. (Harsh, but true!)

In order to be a communication superstar in pandemic dating, you’ll need to get really good at stating your intentions and standards in a really clear, direct way, and getting comfortable asking others about theirs.

In order to do that, you’ll need to master setting really clear boundaries.

Boundaries: The COVID Talk Is the New STD talk. Yay!

The COVID talk is, essentially, the new talk about STDs. It's safety-related, it's uncomfortable, it involves setting boundaries, it happens prior to getting involved with someone new, and everybody would rather avoid it.

Like the STD talk, it's also vitally necessary to ensure that both you and the person you're meeting are on the same page about health and physical boundaries. Skipping this step leads to frustration, confusion, further awkwardness, and resentment.

Especially if we believe that we should be socially distancing right now, it is our responsibility to communicate our comfort level to the people we are seeing.

The essence of boundary-setting is acknowledging that different people have different beliefs, even about things that are very important to us. And it is our job to be honest about our comfort level and beliefs about what is safe for us, even if it differs from another's beliefs. This can be scary and vulnerable - if we're on the more cautious side, some people may think that we're "weird" or "paranoid," and we may think that they're "irresponsible" and "uncaring" - but it's still our job to make decisions that align with our values while refraining from projecting shame onto others for their beliefs.

Make sure you're discussing the virus in "I" terms, you're laying out what you are and aren't comfortable doing with someone new, and you're checking that they're up for being respectful of your boundaries. As your relationship progresses toward physicality, you may need to carry the conversation forward into what their standards are for COVID as well. The key is getting comfortable with setting standards and having an open dialogue.

A Note on Boundary-Setting and Compatibility:

A bonus feature of setting boundaries is that how another person responds to your boundary-setting will tell you a lot about them. Whether you agree or not on COVID, their response should be respectful, and in order for the relationship to progress, the two of you should be able to agree on how to handle distancing in a way that you're both comfortable with.

It's helpful to note that the two of you may have different views on pandemic boundaries and still be able to date. That said, if you can't agree on how to handle the pandemic in a way in which you're both comfortable, that's a non-starter.

So - consider pandemic boundary-setting as an investment in finding someone who not only respects your beliefs, and also an excellent opportunity to practice setting boundaries. Win-win-win.

Pandemic Dating As an Opportunity for: Assessing/Filtering Intentions

When you’re crawling along at a snail’s pace from FaceTime date to FaceTime date, people’s intentions become clear pretty quickly. If you’re seeking a relationship and are concerned about your date just being in it for the physical, virtual dates can be a great way to filter. Those who want something purely casual and/or physical, but who haven’t been forthcoming about their intentions, are unlikely to stick around once you inform them that FaceTime is all that they can expect from your immediate future together.

However, this also means that you need to be proactive and set boundaries. Ask tough questions, be firm in stating that you are not comfortable with meeting in-person until you know each other better, and pay attention to feeling pressured: if you feel like someone is trying to pressure you to meet in-person before you’re ready, that says something in itself, and is an invitation for you to get curious or to set a boundary.

Pandemic Dating As an Opportunity for: Going Deeper With the Relationship

Being limited to conversations in virtual dating also has a way of accelerating the depth of those conversations, and for that reason, the depth of the connection as well. Far-flung as it seems, it’s not unusual during the time of Coronavirus for a FaceTime date to turn into an exclusive relationship to turn into quarantining together and then moving in together within a relatively short period of time. So, as much as virtual dating has us frustrated and feeling isolated, now is arguably a better time than ever for daters looking to form a serious, long-term relationship.

Pandemic Dating As an Opportunity for: Pacing and Slowing Down

I posted a question sticker to my Instagram stories the other week, asking about everyone’s least favorite things about COVID dating. The answers were varied, but the difficulty of meeting people organically, as opposed to online, came up a lot.

I’m not going to pretend - it is harder - a lot harder, to meet people organically in a pandemic. Mostly, because, you know, we aren’t leaving our houses as often these days. But - and don’t hate me - I actually believe that taking some time away from our normal dating structures can be a really good thing.

For those of us who tend to jump into relationships with both feet, pandemic dating can be our opportunity to slow down. With dating moved mostly online, via apps, FaceTime, and Zoom, we have a unique, possibly once-in-a-lifetime opportunity to take things very . . . very . . . slowly.

This might sound awful - no meet-cute, locking eyes with a stranger from across the room, or bumping into a cutie at the grocery store. But - and bear with me - I would argue that online dating gives us a way into move to a new model of finding a partner - one where we pace ourselves, and prioritize compatibility first, and chemistry later.


Putting Compatibility First: A New Model

Ever wonder why you get really attracted to someone and think you know them super-well and then find out later that they have a weird baby teeth collection or they have 6 children? It's because a lot of us tend to not pace ourselves, and dive headlong into new relationships. And that's usually either because of sexual chemistry or internal wiring that tells us WE NEED THIS PERSON AND THEY ARE THE ONE, even though mayyyybe we've only been on like, 3 dates with them.

Chemistry makes it difficult to accurately assess alignment and long-term compatibility with the person seated across from us. Because soul-searing connection is rare, we tend to want to pursue it - even when we suspect that we may not be compatible.

Which is why, for clients who are dating for a long-term relationship, I advocate a model of assessing compatibility first, and following it up with assessing chemistry a little bit afterward.

(For those who aren’t looking for something long-term, this obviously won’t apply - feel free to talk, text, flirt, and have fun! Short-term dating is about learning and having fun, and that can be accomplished - for the most part - with or without compatibility.)

But. For those of us who are looking for lasting connection, focusing on compatibility and pacing can completely revolutionize the quality of our dating interactions.

Online dating, especially online dating during a pandemic, has the “compatibility first” model built-in: we meet someone first online, and then engage in a process of successive filters to see whether we might be compatible. First, we evaluate someone’s profile, then we might engage in some back-and-forth on the app. If that goes well, then we might move on to texting, and then to a phone call. If the phone call goes well, we might move on to a FaceTime date, and then maybe a few more. During all of these interactions, we’ll likely be asking alignment-evaluating questions, like, “What are you looking for in a relationship?” “Are you looking for something serious?” “Do you see yourself having kids?” “What are your career goals, and where do you see yourself in five years?”

Some of these questions will occur when we’re texting; others, maybe, on the phone, and still others via FaceTime. Because our meetings are virtual, it’s still difficult to assess chemistry, and we likely won’t feel a strong connection to the person we’re talking to until a few interactions in: maybe after a FaceTime date or two, or even the first time we meet face-to-face.


When we meet someone first, feel chemistry, and then wait until a first date (or even a couple of dates in) to ask hard-hitting compatibility questions, by then, it’s usually too late (we’re smitten!) to find out that we have drastically different politics or that he isn’t ready to settle down yet, while we want a committed relationship.

By contrast, when we put compatibility first and really slow down our dating interactions - starting with texting or a phone call, and following it up with an in-person or Zoom meeting to assess chemistry, we're building the foundation for more lasting, aligned relationships.

A Note on Proactivity:

Keep in mind - this model requires you to be very proactive during your first couple of interactions. Think of your first few interactions with a new beau less as opportunities for seduction, and more as fact-finding missions. Your in-app text messages and phone calls can be playful and fun, but their main purpose is to “screen” potential dates - Are you basically aligned? Do they sound like someone you could vibe with? - not to create chemistry or sexual tension. There’s plenty of time for that on FaceTime or when you meet in person - after you’ve determined that this is someone who meets your minimum standards for “Potential Future Partner.”

Your willingness to be honest, vulnerable, and direct - with the people you meet and with yourself - is directly proportional to the effectiveness of this strategy. The more you’re willing to have difficult conversations, ask the deep questions, and admit when you might not be a match, rather than allowing yourself to be led by dating fatigue or wishful thinking, the closer you’ll be to honing in on a truly compatible relationship.


A Final Word:

I want you to think of COVID as kind of like scary, contagious training wheels for relational connection.

Dating, with or without a global pandemic, can be difficult and frustrating, and a global pandemic makes it even more complicated.

Butttt. We also have the ability to choose how we see it. We can choose to see these challenges as roadblocks that prevent us from dating, or we can see them as opportunities that can teach us to expand our awareness, our skill sets, and to become more relationship-ready.

These skill sets: communication, boundary-setting, and pacing, are what transform dating from frustrating to fun, and from a struggle to successful.

If all goes well with the Moderna vaccine, COVID will likely soon be on its way out (finally!). When it’s gone, these skill sets will be just as valuable, but the incentive and urgency you get during COVID to learn them won’t be there any longer. They’ll be just as critical, but less urgent, and for that reason, it’ll be easier to ignore and to avoid working on them.

That’s the reason why I advocate learning these skills now: they’re absolutely critical to having a smooth, responsible, and ethical dating experience during COVID; after, they’ll be the skills you need to get into a healthy relationship and keep it strong. Or, if your goals are a little less long-term, to have a fun and mutually rewarding experience while casually dating.

For some people, COVID is going to be the backdrop for their beautiful future love story of resilience, hope, and intentionality. They’ll have met their future partner virtually, and gotten to know them slowly over a series of phone calls, texts, and FaceTime dates, which gradually progressed to Zoom and then (!!) in-person dates. They’ll have asked the tough questions, set boundaries, and learned their partner’s future goals, faults, struggles, and best qualities, and as they moved forward as a couple, there will have been clear communication and mutual excitement to say “yes” to eventually choosing each other in a commitment. When they message me to tell me all about their relationship, months later, I’ll hear about a strong, stable partnership that’s both loving and authentic, and they’ll tell me that they’re looking forward to what their next chapter holds (together!).

I want that for you, too.


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