COVID Chronicles: Dressing Do’s for your Virtual Date


There’s no question – we’re navigating uncharted lands when it comes to creating and fostering romantic connections in 2021. Singles are breaking trail to unprecedented lands, where conventions have given way to new norms and expectations – and it’s yanked many free of their comfort zones, we’re also being presented with rare and refreshing opportunities to take charge of the dating experience in new, creative and thoughtful ways.

Enter stage left: What in the heck is a virtual date and how do I dress for one?!

We find it reassuring that amid all the foreignness, at least one traditional consideration has withstood the assertions of this new era: The importance of presenting oneself well for a first date.

As you begin to put yourself out there, reference this simple guide – We hope it both sets you apart and helps you dress with confidence and authenticity.


Go for it! When preparing to interact with someone new, it doesn’t hurt to go all in – whether your style is clean-cut or more about casual comfort (lounge-wear truly is the best), be intentional about the pieces you choose.

Your date notices the subtle details.

Don’t be afraid to make an impression with a little bling. Watches, yes, and other types of pieces as well. We recommend browsing for jewelry designers and artisans in your city to support local-makers. Other ideas, belt guys rejoice in cool companies like Obscure and Watson & Wolfe making belts now. Be you of course.

Simple, minimalist flare can be both a comfort zone and signature style.

Whatever feels right to you, is right – as long as you’re being intentional.


Don’t overthink it, keep it simple. 

“How many times have you had an outfit in mind, but you tried on 7 other combinations first and wasted 1.5 hours?”

Too many times! If there are a few pieces you love, cut to the chase and wear them. The best part about a first date is – this person has never seen you in your favorite outfit. Use that to your advantage and reallocate that time for something more worth your time… (like a bubble bath, a living room yoga session or taking on a new project).

In other words, when working through all of the pieces and parts, go for pieces you know work – like that perfectly fitting black top and your favorite pair of earrings.

You’ll thank yourself later. Sure, the urge to run out and buy a new dress or off-the-shoulder sweater is compelling, but dating is a mine field of uncertainty already – feeling great in your outfit is something you can control with seldom to no drama.

The more “knowns” are in the mix, the more opportunities to stay grounded in that (highly sought), very delectable state of confidence – all the while braving a new and emotionally charged situation.

Also, sexy is always in! Humankind – we call for taking more pride in your undergarments!

Virtual date or no, eventually you’ll be naked-ish with another human being again… someday. How do you want to show up in that moment?

Go for sexy, go for sweet, go for comfort in your undergarments – however you go – make it you and make it without holes and/or comics from 1988 (unless that’s your thing, totally go for it!).

Something else to think about…

A video date puts you and and your date onto a digital canvas – and like all the best paintings, it’s not just what’s in the forefront that tells a story. The space around (and behind you) is going to tell a tale just as much as your appearance, disposition, tone and body language.

Look around to inspect what’s in the frame… you’ll be wishing you’d taken the time when you spot a pile of crumpled up laundry in the far right corner 15 minutes into your date.

(It happens!). In short, setting up a thoughtful space is totally in-bounds and adds subtle hints about your personality and lifestyle. If you have a great living room and/or art on display that you love, set up with that space as your background. Have a beverage ready, maybe even a snack – something casual and easy to eat such as a flatbread, a cheese plate (grapes are easy and effortlessly sexy), anything in the tapas category.

Have items on-hand (literally) to spark conversation.

No need to overdo it. Generally speaking, a glass of wine, something to snack on and good lighting is all it takes.

This we know: confidence speaks IRL and on-screen. Since you know you best, tap into what you’re needing to feel your best – centered and open. Having trouble tapping into that? Consider leaning into self-care by creating a ritual for your pre-date process.

Taking care of oneself is felt by others – who can sense your ease and contentment. This type of energy helps spark and foster new connections. You can tap into it by checking-in with yourself.

Whatever you’re wearing on your next virtual date, we hope you feel grounded, confident, sexy – whatever it is you want to feel – and that starts and ends with taking care of yourself and your space.

What we like about virtual dating most…

Many of the typically uncontrollable components of the dating scenario are made controllable. You’re at home, safely. You don’t have to catch a cab or walk 8 blocks in the dark. You can cozy up on the couch right after work in your favorite slippers.

Boiled down, the video date format provides a new venue to meet more people in less time, safely. But no matter where you land, virtual dating doesn’t have to be forever for you. Some of our clients, such as those who travel frequently or like the additional privacy, have developed a preference for meeting matches virtually due to the convenience and reduced pressure, while others can’t wait to get back to happy hour evenings and farmer’s market dates.

Our take: That a mix will likely be a good strategy as more venues begin to open and the vaccine becomes more widely distributed – and we’ll be here along the way with tips and tricks. If you missed The 4 Tenets of Pandemic Dating, that’s a good place to go from here.

XOXO, Your Editor & The Heartalytics Team

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