Not Sure of My Situation

[Rollingwithlife]

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...

[Yet another guy]

You may have been friend zoned already, but I recommend you try anyway. What have you got to lose?
You should have made your move when you started getting feelings for her.

You haven't had the fancy dinner yet? Get flirty and ask her if she would like to date you. Avoid ambiguity, obviously.

[Rollingwithlife]

Thanks for the reply!

Haven't done the dinner deal yet - she needed to postpone it due to some sudden change in plans involving something with her family. So out of curiosity, does it even sound like she may have been interested at all?

[Yet another guy]

So out of curiosity, does it even sound like she may have been interested at all?

You can never be sure if there's any interest. Considering the fact that she took initiative contacting you and the amount of time she was willing to spend with you though, she seems more eager than any girl I've ever met. That's quite rare behaviour for a girl.

Good luck on your dinner

[Rollingwithlife]

Thanks! I may even come back to post the results.

Regarding the topic, I'm still interested in other people's responses as well.

[Lulu]

Maybe invite her to do something more casual and spur of the moment that she would hate to refuse- like "I have concert tickets for Tuesday and my buddy had to back out due to work so was hoping you might want to come along with me??" that way the date is at your expense- you are providing a nice time for her making her think of you as being "the man" and taking care of her- and it isn't too much pressure like a fancy, romantic dinner date! That is what I suggest... then try to be a little affectionate at the concert and see how she responds. Not creepy affectionate like gazing into her eyes or groping- just hand on her back or around her waist. Good luck!

[Rollingwithlife]

So in case anyone who read this is interested in what happened, I did finally tell her tonight how I felt as I dropped her off at her house. It was especially difficult on me though, considering that earlier on she told me that the guy she's hanging out with apparently had told her how he felt about her too, and how she was kind of on the fence about it even though she was flattered, she told him that she wanted to remain friends with him for now (and he sort of gave her some attitude about how serious he was), so of course there was more pressure on me to say anything tonight. In any case, the result was that she said she needed to think about it and take it all in, but did mention at some point that she did see me more as a brother than someone of romantic interest and was shocked that I had such feelings for her. For what it's worth, she is very honest in what she says (tells it as it is) and did mention how I thought I was a really great guy and very easy-going and comfortable to be around. I guess as far as the brother comment though, it sounds like she won't ever see me as anything more, but at the same time I'm feeling like maybe she could now that she knows that I'd have such feelings for her? Even after talking this out with her, I'm still contemplating whether to move on completely or consider the possibility of a potential future relationship. Maybe the best thing to do would be to wait a little while and see how it sinks in with her, as I'm sure it was completely left field with her considering how long I've known her for.

[Yet another guy]

Yeah, girls seem to have this tendency to start viewing people the've known for a while as siblings while guys seemingly develop deeper feelings for them.
That's why you should always make it clear to a girl that you're interested in her. She likely won't pick up on signals either.

[Rollingwithlife]

True, but I also didn't want to say anything until I was okay with letting her know how I felt too. I also feel like she's probably seen me as a friend long before I even developed feelings for her, so even the earliest I could have mentioned it and have been truthful in my confession (and I'm always being completely honest when I tell anyone how I feel), I think I would have gotten a similar reply. In any case, I guess only time will tell and at least I implied to her in other words that she now holds the ball, so if by chance she starts feeling the same way, to let me know.