Is it ever appropriate to flirt with a fellow participant during a Zoom call by sending private messages whilst the call is going on?

The group is not work-related. It was set up for the benefit of single people who live alone, who would like to socialise on a Friday evening and are currently unable to because of the lockdown / quarantine.

Both I and the other participant are single and available, I believe there is a good chance I would be compatible with her, and she lives close to me. But, of course, one of the disadvantages of Zoom chats is that you can't make eye contact with another person or have proper one-on-one conversations. There is the facility to send private text messages but I don't know how she'd react to it. So I've come round to the view that it would be a bad idea. For now, I'll just keep up the weekly meetings and try to send out subtle signals that I'm interested in her. When we (the group) are able to have a real-life meeting (March? April?) I can ask her out in person, if I'm still minded to.

In theory, the Wakefield Travelodge would be handy for us both, but Government rules say that visitor accommodation should only open for those who have to travel for work purposes "and for a limited number of other exemptions which will be set out in law”. The exceptions are as yet unspecified. So we'd probably have to take our laptops and work ID. Or bribe the staff, and I don't know what the going rate is.

 

  Thank you for not providing me with more details!

  The only thing you didn’t specify is how long the flirting has gone on (once again, I am NOT asking you to tell me). That makes a big difference on what you should do now before the group meets in March. If you’ve only been flirting a couple of weeks, don’t change anything just yet. If it’s been at least a month, that was over the holidays, so many people are focused on inner circles more than starting something new with an unknown entity. If it’s been a couple of months or more, it’s time to move, Pal, much for the same reason that holidays have ended.

  Some people read more into flirting than is really there. Make sure you’re not misinterpreting her as flirting with you when it’s really just t she’s being nice or being friendly. MANY men make that mistake. “Wow, she really wants me.” The next thing you know, you’re marrying women from Canada or having midnight banter with sapio-sexual types or you have imaginary Harems in your basement or you’re flying to Minnesota every month just to drive past her house and hope she looks out the window right at that second . . . wait, those are purely fictional examples. I digress. Make sure you’re not imagining something that’s not there.

  There is safe flirting and dangerous flirting. For instance, I’m an incorrigible flirt, but a married one who won’t cheat, so when I flirt, it’s not with the ends in mind of making the beast with two backs. Which of you flirted first and the percentage of who flirts more cones into play next. Many women don’t initiate, so if your friend did, there’s hope for you. If you initiated and she warmed up to you, either then or later, there’s hope for you. If there are several restraining orders against you, you’re done.

  Waiting until the whole group meets is too slow. You don’t know if you’re the only peacock strutting around her, and between now and March, someone else’s flumes may flutter in front of her eyes. Waiting until the day of the event might be peacock palace around there, so you want to flourish alone with her prior to. 

  If I were in your position, I’d gauge how serious her flirting is, and I’d consider whether or not my own flirting should advance to an invitation for mugs of hot chocolate [I despise coffee] or something like that. The fact that neither of you are in relationships makes it a green light to me. The only question is timing. Jump too quickly,  and you scare her off (more restraining orders). Move too slowly and she loses interest or thinks you’ve lost interest.
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Thanks for the advice, Randy. By Friday I'll have a plan of sorts. But if it doesn't work out the way I anticipated, I'll accept it with equanimity, as I'm sure other opportunities will arise before long. I'm not putting all my eggs in one basket relationship-wise, just as I'm sure she isn't.

 

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And then there is the reality when you do loose interest and it becomes obvious to her. 

 

  The looseness level of my interest doesn’t waver, it has never increased nor decreased.
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  (Both I and the other participant Both she and I are single)

When listing people, always include yourself last, and she’s not some robotic test subject, she’s not merely a generic faceless vision, she’s the woman in whom you are interested. Loosen up. 

 

  About the TraveLodge: you’re both single, flip a coin as to which of your residences it will be.

You two are the last ones who need an In-And-Out Inn. Free up a room at the local Dodge-Lodge for those who can make the best use of it.

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