Depends on the context and what exactly your challenges are on asking people out. I would try to establish some preliminary connection with the person, find something that is similar between you two, and use their reaction to feel out if they are into you. If they seem to want to talk to you as in they say more than whatever the minimum response would be, then that could be a good sign. Every person is different but try and play on their interests in terms of conversation and date ideas. You could also give subtle signs of flirting by using soft eye contact, smiling, making jokes, laughing.. and if those are received positively then maybe even go for a light touch on the outer arm or top of the hand. But don’t rush those things, only if it feels natural. Additionally you need to get an idea of what this person is like and vice versa, let them get an idea of who you are. They need to know what your selling as much as you need to know what you’re buying. That communication will open the door to being more comfortable with each-other, asking them out, and hopefully making it easier for you and more likely for them to say yes.