I am mildly ashamed that I have to ask such an elementary question, but here I am.
I am at 50+ years of age and 7 years post divorce taking my first plunge into the world of online dating.
I put up my profile and some pictures and at first I was just validation farming with no real intent to start dating while I work on some health issues.
But then things changed and I started seriously considering it. Right now I have 2 women that I am chatting with.
One for about 4 days now, but the pace is slow, basically one back and forth per day with long pauses in between, mostly from her side.
Then yesterday another woman liked my profile so I am also chatting with her.
Tbh I am more attracted to woman #1, but I find both attractive for different reasons
Also tbh there is still a chance I decide I am not ready yet, but at this point I am thinking if all goes well, go on a date/meet and see if maybe I really like one of them.
So my questions:
-I am so far using Chat GPT to help me with general advice, which is perhaps not ideal. But tonight I pasted in one of my responses to woman #1 to see what it thought.
It basically said my responses were ok because they showed that I was listening, but it was not flirty/fun and didn't move the conversation along.
I have to admit, it is harder than I thought to keep a text conversation interesting once you have asked a few basic questions.
So how do you make it more interesting? I feel like I am trying to be polite and nice instead of just being myself.
-how do i know when it's time to ask her out rather than keep texting? Is there a time rule eg 3-5 days? Or depends on how the conversation is going?
-when I do want to ask her out, is it ok to ask her where she wants to go? Give a few options and see what she likes? I know women want men to plan but does that mean I can't ask for input and should just choose whether we go for dinner vs a coffee/walk or something?
-Also in the case that I ask both women out, at what point does it become unethical and I need to decide between one or the other?
Thanks for any responses. I actually have never properly dated since my ex wife and I just kind of got together.