How do you ask someone without being direct?

I'm very VERY shy / introverted

That's okay. They may be your natural behavior, but it's also a choice. You can choose to overcome your social anxiety and be a social person. I was elite levels of shy growing up and I'm still incredibly introverted, but it hasn't prevented me from being a very social person when I want to be. Just because you think you aren't capable of being direct, doesn't mean you shouldn't be.

Here's the problem, you've created this acquaintanceship with this girl that you like through school-related conversation. That's a good starting point and there's nothing wrong with that. The problem is you've kept that as the primary reason to stay in touch. The context of your relationship is strictly about work. You've made no indication that you have a romantic interest in her, so asking her out is going to be a bit unexpected. For that reason, if you want to follow through with your plan, I think you need to be direct. Say, "Do you want to go on a date", and use the actual word date, so she knows what you mean. Obviously this is going to be very sudden.

Here's what I think a better approach is.

"It's awkward to me that we're talking like this a lot but have never even spoken irl do you want to go somewhere and get to know each other better"

Don't do that. In general, don't get in the habit of making yourself look insecure of unsure of yourself. If you build up a good reputation for yourself then it can be okay to call yourself out on your own uncomfortable/anxious feelings, but you must do so from a place of confidence not insecurity.

You stated that you don't talk to her in real life, so start. If you are going to date girls, you're going to have to spend time with them and talk with them in real life. If you can't do in the context of being friends/acquaintances then how can you ever hope to perform well on a date? Start just having friendly conversations. Avoid talking about school as much as possible. Get to know her, and let her know about you. Talk about your hobbies and passions and plans for the future. Become an actual person to her, not just some faceless bot that sends her text messages.

If things go well after that and you develop a good rapport in real life and still think asking her out is a good idea, THEN ask her to get a coffee with you some time. Even if you guys work out great as friends, there is still no guarantee that she has a romantic interest in you. You just have to put yourself in the best position to succeed, then shoot your shot as soon as you can so you don't waste too much time and energy on her.

/r/Advice Thread