What are the appropriate ways to initiate a relationship?

Answer 1

This depends heavily on the person you are trying to initiate a relationship with. Do you want to wow them, sweep them off their feet? Have you known them for a long time, or only a little while, or do you not know them at all? That really should determine how you approach them. If you're friends, just ask them if they are interested in you that way, or ask them if they may be interested in going out on a date. If you haven't known them for very long, asking them to go out on a date is probably your best option. Make sure you are going to do something they want to go do as well--if this person likes music maybe ask if they want to go to a concert, or if they like art an art museum, or if they like coffee a cafe... you get the idea.

If you do ask them out, ask them out yourself. This is a little intimidating sometimes, so maybe you want to send them an email or a note. Make sure you specify that this is a DATE, not a 'hang-out' as that sends the wrong message. Above all, don't be too afraid of rejection. It can hurt to have someone say 'no,' but that just means it wasn't the right person or it wasn't the right time, and it gives you an opportunity to move forward with your life without wondering what could have happened if you never asked at all.