Nervous to ask out brother's friend
Adapted from a recent online discussion.
I've known my brother's friend for years, but I don't know him well. I see him in a group setting every few months, and we have always been flirty. I'd like to get to know him better one-on-one but ... how?
I usually wait for the other person to initiate but that hasn't happened here -- should I take that as a sign?
The thought of asking him out makes me feel like my throat is closing up. The idea of a "date" and sitting across the dinner table from someone making small talk -- hang on, my throat is closing up again ... OK, it passed.
How do people do this?! On a regular basis?!
I'm going to be seeing him at a party in a couple of weeks. Do you have any ideas on how to go about this?
And if you're thinking I should enlist my brother's help in setting me up: He is very protective (and large and intimidating) and his friends are not "allowed" to date me. This could be why the friend is flirty but hasn't tried to take it any further. I don't care what my brother says, but he definitely won't be of any help in making it happen.
-- Asking Someone Out
Have you said to your brother that his protectiveness is anachronistic bull and that the only person who decides who is "allowed" to date you is you?