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Dating Tips

What Not to Wear on a Virtual Date

A date is a date is a date.

If someone invites you to get to know them (or vice versa) with the hope of a romantic connection as a result, that is a date. 

Whether this date takes place over drinks, a picnic in the park, or via Zoom, it is still a date.

So why aren’t we acting like it?

The nationwide quarantine threw single people across the country into a tailspin. How are you supposed to meet someone when you’re not allowed to leave your house? What exactly does “going on a date” even mean right now, and what will it look like in the near future? Is it okay to be thinking about your dating life when we’re in the midst of a pandemic? 

Dating is still on, and love was never cancelled, but in order to continue the search for your ideal match, you might have to tweak the process. Virtual dates—i.e. Video dates via Zoom, FaceTime, WhatsApp, and the like—are very much “real dates,” and you should treat them as such. Rolling out of bed five minutes before Date Night will inevitably give the wrong impression, and for someone who’s putting in the effort to meet someone right now, you’re really not showing that you’re taking it seriously.

While you may have exchanged a few flirty texts or even hopped on a “Hey! I’m real!” phone call with each other, sharing a glass of wine screen to screen is basically the same thing as doing so in a crowded cocktail bar. Save yourself the $14 pour of Sauvignon Blanc and start things off on the right foot by avoiding these 7 waist-up mistakes that should never be worn on a virtual first  date.

1. Dirty T-shirt

You’d think this would be common sense. You’d be wrong. Throwing on the first t-shirt you see laying on your floor communicates to your date, “I couldn’t care less about you,” and/or, “I almost forgot we were doing this entirely.” What a way to make someone swoon, no? Dirty t-shirts are for working out, lounging around, or mowing the lawn, not introducing yourself to the person you could conceivably spend the rest of your life with. 

What to wear instead: Literally whatever you would wear to an in-person date at a bar or restaurant. A button-up shirt, nice sweater, or flattering blouse lets the person you’re meeting know, “I take pride in myself and my appearance, and I respect you enough to put in some effort.”

2. Over-revealing top

Before you think you’re slick by commenting, “Heh heh, but you said a blouse was fine,” let’s back up and realize the difference between a flattering top and one that helps someone get to know a lot more about you than they have a right to on a first date. Something extremely low cut or sheer will be distracting, and while showing off your own brand of sexy is always encouraged, if your date isn’t able to concentrate on your stories about your trip to the Galapagos or your volunteer work with kids, you’re doing yourself a disservice.

What to wear instead: Keep it understatedly sexy. Whatever you’re comfortable and confident in—be that a ruffled neckline or even one-shouldered top that still provides décolleté coverage—will show that you’re comfortable in your own skin, but don’t want your skin to be the only thing they consider about you.

3. Yellow

If yellow is your favorite color, you feel your absolute best when wearing it, and doing so does not mean donning a Spongebob Squarepants t-shirt, then by all means, disregard this Don’t. That said, men and women agree that yellow is an unflattering color on almost everyone. Through a camera’s lens, it can make certain skin tones look pallid or sallow, and can reflect onto the lighter areas of your face making eyes look tired and teeth appear much duller than they are in real life. The brightness should come from your effervescent personality, not your clothing.

What to wear instead: Stick to the classics. Basic shades such as black and navy are universally flattering and won’t compete with the camera. If you’re jonesing for a little more color, jewel tones like emerald green and ruby red can make your eye and hair colors pop without being too jarring.

4. Hats

Many people are currently self conscious about their Quarantine Hair, making feeble attempts to hide their grown-out roots or extra inches of flow under baseball caps and wide-brim fedoras. When you’re making a CVS run, this is fine. But when you’re on a virtual date, you’re casting weird shadows on your face and causing the other person to wonder what exactly you’re hiding under there. The hat is supposed to be working for you, not against you. Take it off.

What to wear instead: If your hair situation really is so dire that you’re embarrassed to be seen, either try styling it in such a way that it’s presentable or simply confess that you, like most people across the country, haven’t had access to a salon or barber shop since March (it’s a great ice breaker!). If you admit that what you’re rocking isn’t your typical ‘do, feel free to send along photos of what you normally look like so they have some frame of reference to compare to.

5. Messy hair

Not wearing a hat does not mean letting whatever was under the hat go unattended to. A lopsided messy bun or rumpled cow lick doesn’t exactly say, “I was looking forward to this!” You could be wearing a stained yellow t-shirt (don’t), but if your hair looks clean and well-groomed, your date might agree to see you again. How well put together you appear starts at the top of your head, so the extra effort will be well worth it.

What to wear instead: While you shouldn’t feel the need to give yourself a Victoria’s Secret-esque blowout or spend 30 minutes perfecting your coif (and if you do, do you), running a brush through your hair and finishing with a spritz of hairspray before the date begins is a smart move. Paired with a nice blue sweater? You’re nailing it.

6. Sunglasses

This is not an early 2000s music video. There is no reason for you to be wearing sunglasses indoors. What people see when you pop up on the screen is their first impression of you, and if you’re wearing your shades inside at 8pm on a Friday, they’re bound to assume that you’re either hungover, high, just coming out of Lasik surgery, or channeling Anna Wintour, and that isn’t a good thing.

What to wear instead: Nothing. There is no alternative here.

7. Distracting jewelry

Cool earrings or an interesting necklace are fantastic conversation starters, and allow you to share your personality without saying a word. Your favorite jewelry will help you feel confident, which is the boost we all need when meeting someone new. Just make sure it’s a silent guest to your virtual date. Bangles jingling, clacking ring stacks, and lip piercings that make you tough to understand are just going to complicate things, and further sidetrack the conversation.

What to wear instead: Give a nod to Coco Chanel and take one thing off before you hit the “Join” button. If you have a signature piece that you always wear, leave it on and talk about it. However, if you’re so weighed down by baubles that you resemble Mr. T and sound like the ghost of Jacob Marley is passing through your living room, it’s all too much. 

Three Day Rule Matchmaking is an exclusive matchmaking company with experts dedicated to helping singles take charge of their dating lives. They customize matches to fit their members’ lifestyles, only introducing them to the best dates. To join Three Day Rule’s free and private online dating pool, sign up here or email Skylar at skylar@threedayrule.com.

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