I've been asked this question directly twice, excluding online 'see how many people you can rack up' requests of course. It is a simple yes or no question granted, but both times I was unsure of what to say.
Once was a cop moonlighting as a security guard in a building where I was temping. The woman who was supposed to give the front desk my name forgot so I had to wait for someone to come down and get me. There happened to be a giant party that day so no one was answering their phone. In the meantime, this guy who introduced himself as Angel began talking to me. When he asked me if I wanted to be friends I honestly didn't hear him. He was a little offended and asked why not when I didn't answer. I said, why not what? He said, be friends. Why is everyone so afraid of cops? I assured him I was not afraid and after a pause relented to being his friend, so long as it didn't require me giving him my number and meeting up with him later. It was awkward but he actually wasn't creepy so it was ok.
The more memorable request occurred while I was in college and sounded something like this:
...
ring, ring...
HB: hello?
M: hi (pause) is HB there?
HB: this is her.
M: hi. um...this is matt somethingorother (pause) i have class with you. 155?
HB: yes, matt. hi.
M: hi. (pause)
HB: so...
M: so...what are you doing?
HB: i'm sorry?
M: (pause) are you busy?
HB: matt can i ask why you are calling?
M: um (long pause) do you want to be my friend?
HB: o wow my dinner is boiling over, I really have to go, I'm sorry- I'll see you in class I can't talk I'm sorry...
clickHB: (to self) no
way that just happened.
Oddly enough, my incredibly compassionate response did not deter him from his plight. He called again another day and my roommate answered, who by now had heard the whole story. I was in the room freaking out about first him calling again and second what she was saying to him.
..
ring, ring...
Roomie: hello?
M: hi (pause) is HB there?
Roomie: who's calling?
M: (pause) this is matt somethingorother (pause) i have class with her.
Roomie: hi matt (my eyes grow very big) HB isn't home right now can I take a message?
M: (pause) um...i have class with her and i wanted to know if she wanted to be friends.
Roomie: matt can i be honest with you?
M: (no response)
Roomie: you really can't just call people up and ask to be their friend. it doesn't work like that.
M: (pause) well how does it work?
Roomie: it has to happen naturally.
M: (pause) but what do i do then?
Roomie: i don't know. you chat with people in class, maybe see if you have the same interests and meet after class. it just develops.
M: (pause) will you be my friend?
Roomie: what did i just tell you?
M: i don't know what to do. i've tried everything.
Roomie: i'm sorry matt. you'll find a friend soon. just let it happen. don't try so hard.
M: ok. bye.
Roomie: bye.
clickI felt extremely bad for him, being that socially inept must be harshly isolating, but really, how does one make it to 19 and not have at least an idea about how to relate to others?