Isn’t the whole point of going online to get offline? (Feel free to read that one again!) So many people ask me, “How do you just get offline?!” Or, “When is the appropriate time to ask someone you’ve met online out on a date … or a video chat?” While there’s no one right answer, I’ll start by saying this: the sooner the better.

Here’s the scenario: you’re having this great exchange of messages with someone on Hinge, for example, but it seems to be leading nowhere. There’s lots of back and forth and maybe even some banter, but there’s no mention of taking it to the next level, whatever “level” that means for you in COVID times. At this point, you have a few options:

1. Stop all communication. Clearly this person has no interest in meeting or talking off the dating site.

2. Keep sending messages for the rest of eternity.

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3. Suggest meeting/talking in a casual, non-aggressive way.

No surprise here … the choice is No. 3: Suggest meeting/talking in a casual way. You might be tempted to just stop writing to someone when it doesn’t seem to be leading to a date, but here’s why I’ll tell you not to do that:

Assume ignorance. These people don’t know what they’re doing, either! They have no idea when it’s appropriate to ask you out! To drive the point home, these are the most common questions I get from my clients: “When do I take this conversation offline? Should I suggest it? How?” Give people the benefit of the doubt.

As to the question of when it’s appropriate to ask: anytime! Let’s say you write to someone and he or she responds. You could ask to chat in the very next message. I’ve found that with my clients, there’s an 80% chance someone will say yes if he or she replied to your first message. You’ve passed the “looks” barrier and the “first message” barrier. You’re in. And of the 20%, they may not have agreed to meet regardless of how many messages you’ve sent! The odds are in your favor. In general, I recommend no more than about six messages back and forth or a week of messaging before scheduling something.

Now, how do you go about doing it? Here are a few examples of how to ask someone out online (well, ask for a video chat — darn COVID):

“I’m really enjoying our conversation. Should we ‘upgrade’ to a video date?”

“I’m really enjoying talking to you! Where should we go from here?”

“That’s a really good question! Much better story told live.”

“You ask great questions. I’m afraid my message back might turn into a novel if I try to answer them all. :) Would a video chat be easier?”

“Not sure the protocol these days, but should we do a video chat one night?”

“COVID dating is weird. Should we upgrade to a video call or something this week?”

Once you put the question out there, the other person has a few choices:

1. Agree.

2. Answer your message but ignore the part about the video date.

3. Not answer at all.

If the latter two, you no longer have to waste your time! And if the first one, you have a date on the books. Congratulations!

Erika Ettin is the founder of A Little Nudge, where she helps others navigate the often intimidating world of online dating. ©2020 Erika Ettin Distributed by Tribune Content Agency, LLC.