Dating is a complicated and often clumsy dance even in the best of times. Add in mask-wearing directives, social distancing and fear of a highly contagious virus for which there is no cure, and you get… well, an awful lot of people going out and doing some version of it anyway. A survey conducted by Everlywell — a company that makes at-home health tests — found that nearly one in four Americans ages 20 to 31 broke quarantine to have sexual contact with someone in April, when stay-at-home orders were at their peak.

How should you navigate a date when you’re not sure a kiss goodbye, let alone an in-person rendezvous, is on the table? Certain dating apps are trying to ease the process. Bumble now lets its users add a badge to their profiles that signifies what kind of dates they’re comfortable with: virtual, socially distanced or socially distanced with a mask. And on Lex, which caters to the queer community, users often preface their personal ads with their Covid-19 or antibody test results, said Kell Rakowski, the app’s founder. Still, meeting up in person — and any physical contact, be it a touch on the arm or sex — requires some pretty candid conversations.

Some people are only comfortable with video dates; others, and this isn’t hypothetical, are still willing to suggest a threesome before noon on a Tuesday. “I definitely didn’t have that one on my pandemic bingo card,” said Jen Livengood, 37, a Nashville television producer. (She declined.)

If you have text or Zoom fatigue, or aren’t in the market for another penpal, find out within the first few messages whether meeting up in person is on the table. Matt Minich, a 33-year-old doctoral student at the University of Wisconsin-Madison, suggests asking, “What does social distancing mean to you?” “A woman asked me that, and it’s a really good way of phrasing it,” Mr. Minich said. “It’s also a way to ask somebody out.”

Other people are more direct, asking for proof of Covid-19 or antibody test results, or suggesting both parties get tested before a meet-up, especially if they live in an area where testing is free. Tarryn Feldman, 36, a makeup artist who works in Nashville’s music industry, gets tested frequently because of her job. She currently has a “friend with benefits” (her description) and is rigorously honest with him about banal interactions that she would never normally discuss. “We check in,” Ms. Feldman said. “I’m not afraid to ask him anything about what he’s been doing and where he’s been.” When a houseguest’s personal trainer tested positive for Covid-19, for instance, Ms. Feldman informed her friend-with-benefits, and everyone got tested. (No one, except the trainer, had the coronavirus.)

For a first in-the-flesh date, keep it outside, where the risk of coronavirus transmission is lower. For the nearly 20 people interviewed for this article, walks were by far the top choice, followed by picnics and then backyard barbecues or a drink at a restaurant with outdoor seating. A clothing designer in Pomona, Calif., who requested anonymity because she didn’t want to be judged for her choices, went over to a man’s house for a dinner of takeout lamb and hummus after he’d produced a screenshot of a negative Covid test — and he’d just had the place cleaned. “He sprayed me down with Lysol and he had a HEPA filter right by his front door, which he said would get all the germs,” she explained. But it didn’t matter: They weren’t a good match and didn’t meet up again.

Nearly all the daters interviewed for this article skipped the masks except if there were other people around — though most know it’s not necessarily a rational choice. “There’s something psychologically when you like someone, you automatically trust that they don’t have the virus,” said Kaley Isabella, 31, who works in public relations in Los Angeles and has been dating a man she met during the pandemic. “It’s crazy. It doesn’t make someone safe just because you like them.”

Marie Helweg-Larsen, a professor of psychology at Dickinson College, says it’s true we are biased toward people we choose to go out with. We tend to underestimate our own risk, she wrote in an email, “and of course we want people we know/love to share our umbrella of invulnerability.”

This thinking can be tough to counteract; it requires recognizing your own bias in your risk assessment. “My best advice is to tell the date beforehand that you intend to wear a mask and would like the date to do so as well,” Dr. Helweg-Larsen wrote. “You can also practice what to say if the date is resisting (something simple like, ‘please put on your mask’ or, ‘you are protecting me with your mask’) or you can use non-verbal communication like stepping or turning away from someone.”

If you choose to mask up — and health experts say you should — expect some mixed signals, or no signals at all. Katie Kirby, 35, a delivery person for DoorDash in Pittsburgh, said face coverings also act as a dating filter; she doesn’t want to be out with anybody who won’t wear one.

But masks increase her anxiety. “I rely on facial expressions so when things are impeded it makes it harder for me to gauge things,” Ms. Kirby said. “And besides worrying that somebody might not be the best person, you’re also worried about a virus.”

For most daters, the biggest question isn’t, “Do you ask before getting physical?” but, “When do you ask?” Inquiring before you’ve met up in person can sound forward, but, according to couples who have already gone on a number of video dates, it’s essential.

“You don’t spend this much time on the phone with someone you don’t want to be physical with,” said Ike Diaz, 39, a video producer in Los Angeles. Mr. Diaz met a marketing manager named Esprit on The League, an app that vets its users based on criteria like where they went to school, for example; they video-dated for more than two months before each got Covid-19 tests so they could meet up for a picnic in late May. Before the date, she asked: “If we were to see each other, would it be an option for us to give each other a kiss?” (Mr. Diaz said that the attraction between the two was “palpable,” but that he had resolved to wait for a signal from her that she was comfortable.)

“I liked that she framed it as a hypothetical, so it wasn’t aggressive,” he said. And, yes, they kissed — and are still together.

If you’re not used to being direct, Rae McDaniel, a certified sex therapist in Chicago, advises calling out any scared feelings. “Saying, ‘I want to ask you something, but I’m nervous you’ll think/do/feel… ’ can turn down the volume on fear quite a bit by naming it instead of trying to ignore it,” said Mx. McDaniel, who uses they/them pronouns. They also suggested following a conversation formula they said has long been used by educators for communicating desires and boundaries about safer sex: Share the risks you’ve taken, then ask about the other person’s risk level and interest in getting closer.

You should also expect to discuss your private life with roommates, even if — and maybe especially if — those are your parents. Jessie Sholl, 51, a writer, left Brooklyn in March to live with her father and stepmother in Minneapolis. After self-quarantining for several weeks, Ms. Sholl wanted to go on an in-person date with a man she’d hooked up with over Christmas and had been Facetiming since she’d been back in town. “I had to tell them he wasn’t some guy I just met — that we had spent the night together,” she said. For the couple’s first in-person date, a socially distanced walk in April, Ms. Sholl’s father and stepmother stood in the doorway waving.

“It was like being back in high school,” Ms. Sholl said. “And then I heard my dad yell, ‘Stay six feet apart.’”

Finally, remember that no amount of coronavirus precautions will protect you from the dogs. After a month of Facetiming, Ms. Livengood went to a man’s house for their first in-person date in his backyard. He grilled filet mignon; she brought Ketel One vodka and mixed French 75s. They stayed six feet apart as he showed her around, but as the cocktails kicked in, “like on any normal date, we got more cuddly and tactile,” she said. They kissed.

At the end of the evening, he took her hands, looked deep into her eyes and said, “If you could just lose 10 or 15 pounds, you would be a knockout and I would consider leaving my girlfriend for you.” Ms. Livengood promptly went home and left her doctor a message about getting a coronavirus test.