This one is a doozy.
My (27f) best friend has been dating her boyfriend (26m) for over 5 years. Awhile back he reached out to me to help figure out ring size and the set up so he could make this the most magical day for her.
Having known my friend for over 20+ years, I know exactly how she wants her proposal to go and who she wants to be there, so I relayed all this information to him months ago via texts and over the phone. I even took the time to covertly find and confirm which ring she would love the most.
A little background: My friend is INCREDIBLY family and friend oriented, and in the past expressed to me on multiple occasions (especially during holiday season) that in the 5 years they’ve been together, he hasn’t really made much of an effort to indoctrinate himself into her family or friendships the way she has for his.