The conversation between human and AI assistant.
How do I flirt with an awkward and shy guy?
That's good advice. What if I want to take things to the next level and ask him out on a date?
If you feel comfortable with it, you could try suggesting a casual hangout or activity that you both enjoy. Something low-pressure like grabbing coffee or seeing a movie could be a good way to get to know him better without putting too much pressure on either of you. Just be sure to approach the invite with a relaxed and friendly tone.