This is my first post here, and I'm really just looking for a spot of advice.
It's quite an awkward post because admittedly, this is stuff that a 30-something woman should have in the bag by now, but I have been out of the dating loop for so long that I'm a little out of my depth when it comes to this stuff.
For a touch of context, I've known this guy since I was in high school. We're now both in our early thirties, and we've remained friends since high school, albeit mainly online friends. It's been a long time since I've seen him in person.
At school, I had feelings for him. It wasn't something that was returned for one reason or another, and so I moved on. Things never got awkward between us. It was what it was. I moved on.
Fast forward a few years, and we're still in contact. Over the years, we've managed to have a few albeit brief conversations over FB but usually, those conversations fizzle out after a day or two. Then we wouldn't speak again for a while after that where the same pattern would arise.
Over the past couple of weeks, things have changed. We're now messaging each other every day, multiple times a day. Often from mid-morning until the early hours. Most of it is just banter, but it's such a difference that I'm curious about him and I want pursue it.
But i'm in a conundrum because I don't want to do anything that may jeopardise a great friendship. If he's not interested in me like that, and I pursue it and have read the signals wrong, it could mean that he would stop talking to me altogether.
Yet, I don't want to potentially miss out on something great (because I really think we'd be great together) just because I was too afraid to try.
So, in your experience, if a guy messages a woman every day, even when he's out with friends, does that indicate some level of interest? I know it's likely that he's just viewing me as another of his friends and I'm barking up the wrong tree (would not be the first time...) but I don't know how to proceed with this one. Or if I even should.