First of all, I'm new here, so "hi" to everyone and it's nice to meet you all .
So I have this childhood friend, one that I used to hang out with when I was younger, but stopped really hanging out with through high school and most of college. In recent years, she was helping my mom choose a dog to adopt (as she's heavily involved in the dog rescue community), and ever since I've been seeing more of her again and recently started to develop feelings towards her. Whether she's interested me, I don't know.
Something important I should mention, is that I started using a dating site about a year ago, and she started using the site herself about a few months ago. Up until she started seeing this guy she met on the site (maybe about a month - month and a half after starting), she used to initiate IM conversations with me frequently, used to ask me to have lunch/dinner with her, see a movie, go to adoption events, etc (anything involving money, we'd go dutch). I feel like the last 'hint' of interest that she may have left me with before these invites started to slow down, is that one day she texted me after she hung out with me in the earlier half of the day, and then the guy she met on the site later in the day, where the text mentioned how she wished I could have stayed longer and that she would have definitely invited me to where she went with this guy, but she didn't want the situation to be awkward. When I texted her back about how it was, she said it was 'fun', but she still wants to go out to eat with me in the next couple days assuming I was available, which I took her up on. So the next day during our lunch together, I asked her again about this guy, and she stated to me that they were just hanging out as friends and that he's a "very nice" guy.
Ever since that day (been a few weeks now, maybe a little more) she's sort of stopped contacting me with the exception of a few hangout invites, but I recently took her up on going to the dog beach with her where I didn't ask, but she updated me on how she was still seeing the guy from the dating site, and how he's "REALLY nice" and that I should meet him to see what I think. I know she's still searching though, as she also brought up how she recently went to a friend's wedding, where she had to stay at her friend's apartment and their roommates were flirting with her and that they were pretty interesting as well.
Finally this week, I decided I'd take matters into my own hands and ask her out to a fancy dinner (aside from a few hangout invites myself earlier on), and she told me she'd go if she had any money. To this I replied that I'd pay for her, to which she replied "aww that's too much", but she agreed to go after I insisted yet again.
Now being the shy guy that I am and not too understanding of women and the hints they drop, would you say this is a case of a girl who was interested in me, but started to feel like it wasn't mutual, hence the slow down of invites and her joining the dating site? I talked to someone else about this too, and she mentioned that the guys she's bringing up with me is to get me jealous and to try to get me to take the initiative with her. I have to admit that most all of my responses to her have been ambiguous though, so she probably doesn't have a clear idea whether I'm interested in her or not. For all I know, maybe she's just being a good friend and I'm reading too much into it - I really have no idea...