reason help: I need dating help! - Help.com

I’m always suspicious of when things go poorly and people don’t know why it happened ^^

Also, in my experience, it’s not enough for a person to be great. You have to be able to get along well with them, their friends, their family, to fit into a lot of the things they enjoy doing. Basically, people live in different environments. And people from too different of environments don’t seem to get along well with each other. So I’d suggest getting to know a lot about him as a friend before deciding to date. I’ve known some people for years, and I’m still surprised when I learn new things about them.

if your friend “Lucy” is REALLY okay with it, and you aren’t afraid of “John” mysteriously dumping you in the same way, then I’d say go for it. But seriously, you need to double triple quadruple check with “Lucy” first because she’s your friend and those kind of situations usually end up only knowing one of the two people involved afterwards. As in, it’s either “Lucy” or “John”. Can’t have both.

Also, I can’t help noticing (And I may be completely off here) that this John might have left Lucy for you.
Eh?

Well, in the right context, dating doesn’t make things awkward if it’s a continuation and deepening of a friendship.
I think some people go about it wrong when they get too focused on trying to have ‘romantic’ dates. Dating can be merely spending time with someone you enjoy spending time with, and pursuing a much deeper friendship.
Perhaps that’s because many people date without considering what their goal in dating is. Where do you want it to go and what is the outcome you desire? Because knowing where you are going and where you are helps finding out how to get there.