Hi Mr Kip,
I'm a 22 year old guy and have always really struggled with relationship stuff but I'd like to help as best I can (I guess so others don't go through the same pain as me!) - could I ask are you someone who is still at school or are you at uni age? What sort of context are we dealing with, a fellow student or...?
Basically, yes I think something like a coffee date is an ideal place to start. To actually ask them out, I think you do need to go through a sort of routine of calming yourself through deep breathing and then sort of pumping up your confidence as best you can - not to the extent you end up talking really loudly etc. but just so that you have a sense that you appear confident and relaxed (even if you don't feel it inside!). Maybe try starting a conversation just with an unrelated question (Hi, how're you going, I heard that you recently did this/that, how was it?) and remember to smile! Smiling is the best, both for making you feel better, and for appearing confident/at ease with yourself - be prepared to laugh at yourself if you feel like you appear nervous. Even be open about how you are feeling eg 'look I feel a bit nervous about asking this but would you like to grab a coffee with me sometime?'
I know how terrifying it can be - honestly I do - but well done for even getting to the point of seriously considering it! I had a long term crush for years who I never asked out - I regret it all the time unfortunately! You might as well take the chance and gain the experience! Let me know how you go!
Hugh
