Edit: I'm not sure how to edit the title. I meant "noob needs advice"

I am a super noob with flirting. I have never had idea how to do it. In the past, when I was younger, I tried some awkward attempts but always failed and felt ridiculous, embarrassed, so I decided to give up and wait for girls to make the first move. After all for them it's easier, I thought. They have higher chances of success.

So all the girls I've been with are girls who made the first move or girls met on a dating app or clubs.

Dating apps are different because there is a sort of codified behaviour behind them: you match, you chat, you ask them out. When you're out you know why you're out and if they accept to see you a second time you know you've been successful.

Club interaction is more or less codified too. If I approach a girl, it's obvious what I want. If I ask for her phone number and she gives it to me and if then we text and meet again it's all an obvious codified behaviour which both of you know.

What really confuses me though is flirting with someone you met outside of such contexts. Everything is very ambiguous and this is the territory where I gave up and started waiting for their move.

A colleague or a friend of a friend for example.

So, because I want to grow up, because I want to dump dating apps and because I'm tired of being chosen and want to start choosing I decided I have to risk again. I have to walk outside my comfort zone and map this unknown territory by making mistakes.

There's this colleague, I've always liked her. We both share interest for metal music so we started talking about it. I started feeling like she found excuses to talk to me (but this might have happened just in my perception).

One day, because I just wanted some physical interaction with her, I poked her side, under the ribs while she was walking past me. She laughed and she poked back and every time she met me afterwards she poked me playfully in the same place.

I took that as a good sign.

I also had the feeling she kind of blushed every time she was talking to me.

This went on for 3 or 4 months. Then she went away, to the upper floor, working in the same hospital but different ward and place.

Once I commented one of her Facebook stories teasing her. We chatted a bit but she was a bit passive and the convo ended at some point.

One day I met her by chance and since we had a night out planned with my colleagues (she knows all of them and some of them are her close friends) I invited her. She accepted. I said that to the guy who was organising the night out and she was added to the list for the restaurant. The rest of the communication with her was done by her friends to arrange the night.

2 days before the night out though she messaged me on Facebook messenger saying "heyyyyy, Friday?". We texted a bit etc etc etc but she had no reasons to message me because she communicated with her friend about the night out. So I took that as a good sign. The conversations ended soon too tho. She ended it with "see you there".

She didn't make it to the night out because one of her kids was sick.

The day after I texted her, asking if everything was OK. We texted for a bit, she asked questions about the night, if we had fun, how the food was, the she ended it. I tried to continue asking about her plans for the weekend but her replies where quick, to the point and self conclusive so I dropped it.

Every time we're texting there is the same pattern. She talks, she laughs, once she even messaged me first, she interacts playfully until a certain point when she drops it.

I didn't know what to do. I thought the poke and all the rest, the fact she accepted my invite (but her friends were there so probably this does not count), the fact she messaged me before the night out, as signs of interest in some way.

If she was more talkative in the chats it would have been natural to ask her out but she cut every single conversation.

So I didn't know what to think but I knew I wanted to do that leap out of my comfort zone and risk it.

So 3 or 4 days later I texted her

- how was you weekend spent cleaning the house?

- it was fun ahahah. I didn't do much really.

(another self conclusive message that cut the conversation so I thought I'd cut to the chase and get my answer)

- when you want a break from house chores let's go for a drink.

- live music ahahah

- sounds like a plan. I'm on call this Saturday tho so let's have a look what's on next weekend.

- sure! I can't this weekend too as it's midterm.

- cool! Let's keep an eye on what's on next weekend then.

- sounds good.

OK. She accepted my invite.

Now, Because I went way out of my comfort zone and because I haven't really mapped this territory I'm feeling anxious and I would like a hand to read the situation.

Did she get what my intentions are? Is she interested or she thinks we're friends?

What do I do now? I was thinking to wait a few days just in case she messages me, otherwise Wednesday or Thursday I message. I'll have a look for any musical events in town and propose them. If there isn't any interesting events I'll write something like "didn't find any interesting live music events but we can still go for a drink. At the end the company is what matters more".

Is that a good strategy? Or shall I drop it if she doesn't message me because it shows she's not interested?

Thank you in advance and please be merciful and patient with a noob.