In need of a bit of advice

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I'm totally inexperienced when it comes to relationships/dating, so I think I need a bit of advice on this before I decide what to do. Sorry if this is a bit long, any advice on it though would be very much appreciated!

There's a girl who used to go to the same school as me (we've since both left), we always used to get on well and we share some similar traits/opinions/interests too. We were never really close at school but she was always around and I'd talk to her fairly often. I've been attracted to her for a while.

Before Christmas I messaged her on Facebook (we were friends on there) to ask her about her thoughts on something we'd both been invited to. I obviously asked how she was doing too. I hoped deep down it would lead to more than that though.

Her response was really nice, she said it was really nice to hear from me which took me by surprise! Was not expecting her to be so interested in my message. So we ended up having a really good conversation on there for a number of weeks, and I found out we had more in common than I first thought too.

The thing we'd both been invited to ended up not happening, so I thought I'd be brave and ask her if she wanted to meet up with me sometime - without confessing how I actually felt about her. My reason for doing this was because I wanted to get to know her a bit better first before I decided whether I'd want to take it any further.

We did meet up last month and I think it seemed to go OK. I think I showed I was nervous but there weren't any awkward moments and the conversation was pretty much constant. Considering I'd never met up with a girl like that before I was pretty happy with how it went. I did really enjoy talking to her and I feel like if we met up again things would be so much easier. She seemed interested in seeing me again and we've spoken since too.

Basically, I'm really nervous to confess to her how I really feel. I'm just so worried it will go wrong and end up making things incredibly awkward. I'm also not sure of the right way to do it and I don't want to come across as too desperate etc.

What would be your advice in this situation? Should I just be honest with her and take the risk? And if so, how should I tell her? I'm also thinking 'what if she has a boyfriend' even though I'm 99% sure she doesn't and has never mentioned one.

In my opinion you got the hardest parts out of the way, initiating a meeting and keeping conversation going.

Just ask. If she's not interested you'd rather find out now before you get too much more attached. If you're really into her finding out she's not into you like that will hurt more the more time that passes.

I think it's going well so far, but you need to be careful and take it steady. I wouldn't rush something like this. What I would recommend is seeing how far you can get to being close to her, see if there's any slack you need to pick up before making any kind of move, and if you think that you've gotten as close as you ever could manage then "confess" after that.

I wouldn't want you to get ahead of yourself, but you don't necessarily have to take this advice. That's just my whole perspective on it.

I am far from a relationship expert, but I am married so I must have done something correct. I agree with the other posts, you don't really need to confess to how you feel about her, at least not yet. I would continue to talk with her via facebook or the phone, and try to get together for some more dates. I think the way you feel about each other will become apparent by these interactions, even if it is really hard for us Aspies to pick up the non-verbal cues. If she wants to continue to get together with you, then there must be something she really likes about you.

Thank you very much for all your advice, I think I'll probably try and go for a mixture of both the 'upfront' approach and the more distant approach. I do want to tell her how I feel because I'm not the greatest at picking up cues and understanding people's body language, so I feel like it would make sense just to be honest with her and see how she reacts. But at the same time, I'm not just going to come out and say it, I'll try and build up to it in conversation somehow and see how it goes.

Part of my reason for wanting to tell her upfront is because I've been way too cautious in the past with girls, I've always either never had the confidence to say anything or always made the classic mistake of 'waiting for the right time'. Part of me thinks I ought to just take a risk and maybe it will pay off.

It's also pretty hard to tell what someone thinks through messages, although she's been using lots of emojis which might be encouraging!

Should I wait until after the 14th to message her again do you think? Maybe its just me but I don't want her to think I'm doing it 'because its valentines day', that would just be so cheesy and awkward IMO.

The counter point here is, if she IS interested in you that way, not saying anything to her whatsoever on Valentine's Day would probably send the wrong message. It may make you appear disinterested or insensitive. I'd save "the question" for later, but at least send some happy V-Day wishes. Don't have to be a big gesture at all, but don't ignore it altogether either.

There is a fine line between rushing and taking a pragmatic approach, and it's difficult to tell either way which is which at times. I think taking it quickly could either pay off or be hazardous, but it's your decision if you want to take the 50/50 risk (it would be swayed a lot more in favour of either if you were to understand even a little about how close you both are).

Anyways, I wish you the best of luck.

What if she is wanting you to ask her out before valentine's day?

I don't know your situation well enough to give you advice on what to do, but I hope for your sake, things turn out for you the best way it possibly can for how either of you may feel for each other. I don't necessarily adhere to gender roles, so I'm more in the camp that if someone likes me enough or is interested in getting to know me better, they can initiate just as much as I can (and I hope they ask me out). That may also explain why I am not getting any traction anywhere when it comes to relationships, but it seems like a good thing that there are plans to see her again.