3 Steps To Keep the Conversation Going When You Can’t Meet In Person Because of the Gosh Darned World Pandemic

Advice by Chloe
5 min readApr 23, 2020

Most of my clients since the pandemic are struggling with conversations that lag or die out because they’re unable to transition from the dating app to an actual date. The struggle is understandable. It’s really hard to maintain a dynamic conversation via text for a long period of time. The conversation eventually falters, neither party knows what to say next, and the budding connection just sort-of dies. It sucks, but it’s a familiar reality to most of the people who are trying to date during this unique circumstance. It doesn’t have to be that way though. I even wrote each step down, just for you. I call it the STAIRCASE OF LOVE. Just joking, I don’t really call it that. It doesn’t have a name, but it’s really fucking useful. Here we go:

  1. Build her interest in you by focusing on what’s important to her and then asking questions about it.

Does she love skiing? Ask her about it- but do it in a personal way. Ask her questions she’ll have an emotional response to. You’re trying to build a connection with her and create a sense of familiarity.

  • ❌ “Where did you go on your last skiing trip?” If you ask a close-ended question, you will probably get a close-ended answer. Avoid questions that can be answered in one or two words.
  • ❌ “What was your last skiing trip like?” Don’t ask questions that are overwhelmingly broad. It’s difficult to answer because it’s so vague, and she’s likely to resort to a one or two worded nonanswer. When someone asks you how your day has been, you don’t give them an in-depth account, you say “it was good” and move on. Vague or super broad questions aren’t helpful for facilitating conversation.
  • ✔️ “Oh wow, that’s so cool! I never learned how to ski. What do you love about it?” You’re facilitating connection by asking her a question that will lead to an emotional response. Her answer will teach you so.much.more about her that the previous two, and it will be easier to turn into an engaging conversation.

2. Transition off the app

  • ❌ DON’T ask until you’ve built chemistry. Wait until she’s engaged in the conversation and clearly into you. If you try to transition too quickly, she won’t be invested enough to say yes, and she probably won’t say no- she’ll just ghost you.
  • ❌ DON’T wait too long. You should do it during the first conversation that the two of you develop chemistry. Don’t chicken out, don’t put it off. Do it at the height of chemistry.
  • ❌ DON’T ask for her number. A lot of girls are wary about giving out their number, and if she feels uncomfortable or awkward she’s unlikely to be straightforward about it, she’ll probably just ghost you.
  • ✔️Instead, give her your number, and tell her that you’d love to switch to text as soon as she’s comfortable. That way, if she’s cool with it, she’ll text you- but if she’s not ready yet she won’t feel pushed into a corner. “ I had a blast hanging out with you today. I haven’t had this much fun on Tinder in ages. I have to head to bed, but here’s my number. I’d love to switch over to text whenever you’re comfortable. No pressure though :)”

3. Ask Her Out On A Virtual Date

  • ❌ Texting is not a date. It’s a great way to develop some chemistry, get some witty banter in there, but it’s hard to keep a text conversation going for a long period of time and it takes a lot of work to keep it interesting.
  • ❌ A voice/video call is not a date. It’s a lot more personal than texting, and it’s great at increasing your connection and familiarity with each other- but when the conversation starts to dry up it’s going to get awkward. You don’t want a phone conversation to become a source of stress or to get boring.
  • ✔️ voice/video call + activity = date. Play Words With Friends, Draw Something, or an online board game together. You could buy Tabletop Simulator for less than the price of dinner and have an endless number of online board games to play, you could watch a movie, you could play Two Truths and a Lie, you could play 20 Questions, you could cook dinner together on video chat, etc… Your options are pretty limitless.
  • ✔️ Treat it like a date. Use the word date when you ask her, set a time and day, and then have everything prepared beforehand. If you want to play Two Truths and a Lie, go ahead and be thinking of a few interesting truths about yourself. If you want to play Tabletop, gift her the game if she doesn’t already have it, add her on Steam, and play a practice game with a friend if you aren’t familiar with the platform. If you want to watch a movie, make sure that you both have whatever streaming service it’s on. Preparation is key.

Virtual dating doesn’t have to be soul-crushing. The current state of our world isn’t ideal, but humans are pretty adaptable. Don’t get stuck in the same pattern, don’t try to carry on a text conversation for 3 months and expect it to end with a date, and don’t be too stubborn to adjust to your surroundings. You’ve got this… and if you don’t, you’ve got me. Hit me up and I’ll get you sorted ;)

If you’d like to book an appointment to improve your dating profile, learn how to build chemistry, or get a gift card for a friend, hit me up. If you’re on the fence, check out my testimonials!






Advice by Chloe

Dating consultant who got her start on Reddit. I write about dating and relationships and I’m always trying to make dating easier for dudes. AdvicebyChloe.com