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I'd freak out if there were a question in every text. It's just not feeling comfortable.
I'll add that I'm a huge texter and texted with my bf every day (many texts per day) for 4 weeks before our first date.
The conversations will flow naturally if both are engaging.
With my bf, we didn't do many questions. Actually, I avoided them and at one point made the comment "oh no, not interview mode." He picked up on it. We touched all important topics by just letting the conversation flow.
Instead of questions in every reply to pass the ball back to the other. I find that the key is to keep it light and playful, yet with honesty and sharing who you are. Some banter to keep it going. If the other person is interested and compatible with me, they will be at the same level.
Helpful for me to think about. To me, leaving out a question is something I took to be a lack of interest in asking about the other person. But I can see I'm taking that very literally.
I think "light and playful" is where I went wrong here. For me, I want something more than light and playful. I did ask about prior relationships: what's something you learned in your last relationship that you want to bring to your next one?
To me, that's trying to get beneath the surface and understand what another person is looking for in a relationship. It seems like a totally normal thing to ask once you're past 40 and looking for a long-term relationship. But I'm also learning it's probably too intense for an initial conversation.
This is the kind of question that could be more natural in person but can easily feel like a canned way of testing somebody when asked over text.
Ahh. I see. Thank you for pointing this out.