Why won't he ask me out

Samantha • 🤷🏼‍♀️🤷🏼‍♀️🤷🏼‍♀️

I like a guy, and I'm pretty sure he likes me too. I flirt with him but he has only the most awkward and stupid responses like, "yeah lol" sometimes he flirts back but honestly it can be so hard, because he is terrible at holding a conversation. I tried hinting that I wanted to go somewhere but I had no one to go with, but he didn't take the hint. I really like him and we've been talking for like 2 weeks but I'm getting so tired of this and my family is just telling me to drop him, what should i do?