He's shy and NEVER initiates anything.. but I'm totally smitten! He seems to always be happy to hear from me but because he is so reserved about his feelings, I am terrified that I might be over stepping my bounds (as the woman/pursuer) so I only message him like a couple times a month. This is getting me NO WHERE! If you were/are a shy guy, could you give me some ideas of how you wish a girl you like would pursue you? Or perhaps she already got you and you have a story of how she accomplished breaking into your shell? Please share! Thanks :)
Most Helpful Girl
You can't beat around the bush with shy guys, you have to be direct about what you want. Some shy guys are easily frieghtened like deer, so be blunt and forward without being crude.
Simply ask him out on a date. A legit date. Don't use code words like hang out or chill, use the word date.
After the 2nd or 3rd date ask him if hell be your boyfriend
Bada being bada boom, simple.1